Mechanisms of Bisphosphine Iron-Catalyzed C(SP²)-C(SP³) Cross-Coupling Reactions: Inner-Sphere or Outer-Sphere Arylation?

References

• de Meijere, A.; BräSe, S.; Oestreich, M.; Eds.; Metal‐Catalyzed Cross‐Coupling Reactions and More, 1, 2 and 3; Wiley-VCH Verlag GmbH: Weinheim, 2014.
   Google Scholar
• Briffis, A.; Centomo, P.; Zotto, A. D.; Zecca, M. Pd Metal Catalysts for Cross-Couplings and Related Reactions in the 21st Century: A Critical Review. Chem. Rev. 2018, 118, 2249–2295. DOI: 10.1021/acs.chemrev.7b00443.
   PubMed Web of Science ®Google Scholar
• Seechurn, C. C. C. J.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize. Angew. Chem. Int. Ed. 2012, 51, 5062–5085. DOI: 10.1002/anie.201107017.
   PubMed Web of Science ®Google Scholar
• Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis. Angew. Chem. Int. Ed. 2005, 44, 4442–4489. DOI: 10.1002/anie.200500368.
   PubMed Web of Science ®Google Scholar
• Kharasch, M. S.; Fields, E. K. Factors Determining the Course and Mechanisms of Grignard Reactions. IV. The Effect of Metallic Halides on the Reaction of Aryl Grignard Reagents and Organic Halides. J. Am. Chem. Soc. 1941, 63, 2316–2320. DOI: 10.1021/ja01854a006.
   Google Scholar
• Tamura, M.; Kochi, J. Vinylation of Grignard Reagents. Catalysis by Iron. J. Am. Chem. Soc. 1971, 93, 1487–1489. DOI: 10.1021/ja00735a030.
   Web of Science ®Google Scholar
• Tamura, M.; Kochi, J. Coupling of Grignard Reagents with Organic Halides. Synthesis. 1971, 303–305. DOI: 10.1055/s-1971-35043.
   Google Scholar
• Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. DOI: 10.1021/cr00039a007.
   Web of Science ®Google Scholar
• Stille, J. K. The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]. Angew. Chem. Int. Ed. 1986, 25, 508–524. DOI: 10.1002/anie.198605081.
   Web of Science ®Google Scholar
• Negishi, E. Palladium- or Nickel-Catalyzed Cross Coupling. A New Selective Method for Carbon-Carbon Bond Formation. Acc. Chem. Res. 1982, 15, 340–348. DOI: 10.1021/ar00083a001.
   Web of Science ®Google Scholar
• Martin, R.; Buchwald, S. L. Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands. Acc. Chem. Res. 2008, 41, 1461–1473. DOI: 10.1021/ar800036s.
   PubMed Web of Science ®Google Scholar
• For Recent Reviews on Nickel-Catalyzed Cross-Coupling Reactions, See: (A) Tasker, S. Z.; Stanley, E. A.; Jamison, T. F. Recent Advances in Homogeneous Nickel Catalysis. Nature. 2014, 509, 299–309. DOI: 10.1038/nature13274. (b) Weix, D. J. Methods and Mechanisms for Cross-Electrophile Coupling of Csp2Halides with Alkyl Electrophiles. Acc. Chem. Res. 2015, 48, 1767–1775. DOI: 10.1021/acs.accounts.5b00057. (c) Klein, A.; Sandleben, A.; Vogt, N. Synthesis, Structure and Reactivity of Cyclometalated Nickel(II) Complexes: A Review and Perspective. Proc. Natl. Acad. Sci., India, Sect. A Phys. Sci. 2016, 86, 533–549. DOI: 10.1007/s40010-016-0289-6. (d) Budnikova, Y. H.; Vicic, D. A.; Klein, A. Exploring Mechanisms in Ni Terpyridine Catalyzed C–C Cross-Coupling Reactions—A Review. Inorganics. 2018, 6, 18. DOI:10.3390/inorganics6010018.
   PubMed Web of Science ®Google Scholar
• Han, F. Transition-Metal-Catalyzed Suzuki–Miyaura Cross-Coupling Reactions: A Remarkable Advance from Palladium to Nickel Catalysts. Chem. Soc. Rev. 2013, 42, 5270–5298. DOI: 10.1039/C3CS35521G.
   PubMed Web of Science ®Google Scholar
• The cost of Iron and palladium comes from Sigma-Aldrich, Inc., United States, 2018.
   Google Scholar
• Barbalace, K. Periodic Table of Elements. EnvironmentalChemistry.com (accessed April 14, 2007).
   Google Scholar
• U. S. Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research (CDER), Center for Biologics Evaluation and Research (CBER). Q3D Elemental Impurities Guidance for Industry. September, 2015.
   Google Scholar
• Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Functionalization of Organic Molecules by Transition‐Metal‐Catalyzed C(sp3)-H Activation. Chem. Eur. J. 2010, 16, 2654–2672. DOI: 10.1002/chem.200902374. For reviews using alkyl halides in cross-coupling reactions, see: (a) Rudolph, A.; Lautens, M. Secondary Alkyl Halides in Transition-Metal-Catalyzed Cross-Coupling Reactions. Angew. Chem. Int. Ed. 2009, 48, 2656–2670. DOI: 10.1002/anie.200803611. (b) Sherry, B. D.; Fürstner, A. The Promise and Challenge of Iron-Catalyzed Cross Coupling. Acc. Chem. Res. 2008, 41, 1500–1511. DOI: 10.1021/ar800039x. (c) Bauer, I.; Knölker, H.-J. Iron Catalysis in Organic Synthesis. Chem. Rev. 2015, 115, 3170–3387. DOI: 10.1021/cr500425u. (d) Jana, R.; Pathak, T. P.; Sigman, M. S. Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners. Chem. Rev. 2011, 111, 1417–1492. DOI: 10.1021/cr100327p.
   PubMed Web of Science ®Google Scholar
• (A) Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. Iron-Catalyzed Cross-Coupling of Primary and Secondary Alkyl Halides with Aryl Grignard Reagents. J. Am. Chem. Soc. 2004, 126, 3686–3687. DOI: 10.1021/ja049744t. (b) Hatakeyama, T.; Kondo, Y.; Fujiwara, Y.; Takaya, H.; Ito, S.; Nakamura, E.; Nakamura, M. Iron-Catalysed Fluoroaromatic Coupling Reactions Under Catalytic Modulation With 1,2-Bis(diphenylphosphino)Benzene. Chem. Commun. 2009, 0, 1216–1218. DOI: 10.1039/B820879D. (c) Hatakeyama, T.; Hashimoto, T.; Kondo, Y.; Fujiwara, Y.; Seike, H.; Takaya, H.; Tamada, Y.; Ono, T.; Nakamura, M. Iron-Catalyzed Suzuki-Miyaura coupling of Alkyl Halides. J. Am. Chem. Soc. 2010, 132, 10674–10676. DOI: 10.1021/ja103973a. (d) Hatakeyama, T.; Okada, Y.; Yoshimoto, Y.; Nakamura, M. Tuning Chemoselectivity in Iron‐Catalyzed Sonogashira‐Type Reactions Using a Bisphosphine Ligand with Peripheral Steric Bulk: Selective Alkynylation of Nonactivated Alkyl Halides. Angew. Chem. Int. Ed. 2011, 50, 10973–10976. DOI: 10.1002/anie.201104125. (e) Hatakeyama, T.; Fujiwara, Y.; Okada, Y.; Itoh, T.; Hashimoto, T.; Kawamura, S.; Ogata, K.; Takaya, H.; Nakamura, M. Kumada–Tamao–Corriu Coupling of Alkyl Halides Catalyzed by an Iron–Bisphosphine Complex. Chem. Lett. 2011, 40, 1030–1032. DOI: 10.1246/cl.2011.1030. (f) Hatakeyama, T.; Hashimoto, T.; Kathriarachchi, K. K. A. D. S.; Zenmyo, T.; Seike, H.; Nakamura, M. Iron-catalyzed alkyl-alkyl Suzuki-Miyaura coupling. Angew. Chem. Int. Ed. 2012, 51, 8834–8837. DOI: 10.1002/anie.201202797. (g) Kawamura, S.; Nakamura, M. Ligand-controlled Iron-catalyzed Cross Coupling of Benzylic Chlorides with Aryl Grignard Reagents. Chem. Lett. 2013, 42, 183–185. DOI: 10.1246/cl.2013.183. (h) Nakagawa, N.; Hatakeyama, T.; Nakamura, M. Iron-catalyzed Suzuki–Miyaura Coupling Reaction of Unactivated Alkyl Halides with Lithium Alkynylborates. Chem. Lett. 2015, 44, 486–488. DOI: 10.1246/cl.141167. (i) Adak, L.; Kawamura, S.; Toma, G.; Takenaka, T.; Isozaki, K.; Takaya, H.; Orita, A.; Li, H. C.; Shing, T. K. M.; Nakamura, M. Synthesis of Aryl C-Glycosides via Iron-Catalyzed Cross Coupling of Halosugars: Stereoselective Anomeric Arylation of Glycosyl Radicals. J. Am. Chem. Soc. 2017, 139, 10693–10701. DOI: 10.1021/jacs.7b03867.
   PubMed Web of Science ®Google Scholar
• Dongol, K. G.; Koh, H.; Sau, M.; Chai, C. L. L. Iron‐Catalysed Sp3–Sp3 Cross‐Coupling Reactions of Unactivated Alkyl Halides with Alkyl Grignard Reagents. Adv. Synth. Catal. 2007, 349, 1015–1018. DOI: 10.1002/adsc.200600383.
   Google Scholar
• (A) Bedford, R. B.; Huwe, M.; Wilkinson, M. C. Iron-Catalysed Negishi Coupling of Benzylhalides and Phosphates. Chem. Commun. 2009, 600–602. DOI: 10.1039/B818961G. (b) Adams, C. J.; Bedford, R. B.; Carter, E.; Gower, N. J.; Haddow, M. F.; Harvey, J. N.; Huwe, M.; Cartes, M. A.; Mansell, S. M.; Mendoza, C.; Murphy, D. M.; Neeve, E. C.; Nunn, J. Iron(I) in Negishi Cross-Coupling Reactions. J. Am. Chem. Soc. 2012, 134, 10333–10336. DOI: 10.1021/ja303250t. (c) Bedford, R. B.; Carter, E.; Cogswell, P. M.; Gower, N. J.; Haddow, M. F.; Harvey, J. N.; Murphy, D. M.; Neeve, E. C.; Nunn, J. Simplifying Iron–Phosphine Catalysts for Cross‐Coupling Reactions. Angew. Chem. Int. Ed. 2013, 52, 1285–1288. DOI: 10.1002/anie.201207868. (d) Bedford, R. B.; Brenner, P. B.; Carter, E.; Carvell, T. W.; Cogswell, P. M.; Gallagher, T.; Harvey, J. N.; Murphy, D. M.; Neeve, E. C.; Nunn, J.; Pye, D. R. Expedient Iron‐Catalyzed Coupling of Alkyl, Benzyl and Allyl Halides with Arylboronic Esters. Chem. Eur. J. 2014, 20, 7935–7938. DOI: 10.1002/chem.201402174.
   PubMed Web of Science ®Google Scholar
• Sun, C.-L.; Krause, H.; Fürstner, A. A Practical Procedure for Iron‐Catalyzed Cross‐Coupling Reactions of Sterically Hindered Aryl‐Grignard Reagents with Primary Alkyl Halides. Adv. Synth. Catal. 2014, 356, 1281–1291. DOI: 10.1002/adsc.201301089.
   Web of Science ®Google Scholar
• (A) Toriyama, F.; Cornella, J.; Wimmer, L.; Chen, T. G.; Dixon, D. D.; Creech, G.; Baran, P. S. Redox-Active Esters in Fe-Catalyzed C–C Coupling. J. Am. Chem. Soc. 2016, 138, 11132–11135. DOI: 10.1021/jacs.6b07172. (b) Edwards, J. T.; Merchant, R. R.; McClymont, K. S.; Knouse, K. W.; Qin, T.; Malins, L. R.; Vokits, B.; Shaw, S. A.; Bao, D.-H.; We, F.-L.; Zhou, T.; Eastgate, M. D.; Baran, P. S. Decarboxylative Alkenylation. Nature. 2017, 545, 213–218. DOI: 10.1038/nature22307. (c) Sandfort, F.; O’Neill, M. J.; Cornella, J.; Wimmer, L.; Baran, P. S. Alkyl−(Hetero)Aryl Bond Formation via Decarboxylative Cross‐Coupling: A Systematic Analysis. Angew. Chem. Int. Ed. 2017, 56, 3319–3323. DOI: 10.1002/anie.201612314.
   PubMed Web of Science ®Google Scholar
• (A) Tellis, J. C.; Primer, D. N.; Molander, G. A. Single-Electron Transmetalation in Organoboron Cross-Coupling by Photoredox/Nickel Dual Catalysis. Science. 2014, 345, 433–436. DOI: 10.1126/science.1253647. (b) Hartwig, J. F. Organotransition Metal Chemistry: From Bonding to Catalysis; University Science; Sausalito, CA, 2010.
   PubMed Web of Science ®Google Scholar
• Daifuku, S. L.; Kneebone, J. L.; Snyder, B. E. R.; Neidig, M. L. Iron(II) Active Species in Iron–Bisphosphine Catalyzed Kumada and Suzuki–Miyaura Cross-Couplings of Phenyl Nucleophiles and Secondary Alkyl Halides. J. Am. Chem. Soc. 2015, 137, 11432–11444. DOI: 10.1021/jacs.5b06648.
   PubMed Web of Science ®Google Scholar
• Daifuku, S. L.; Al-Afyouni, M. H.; Snyder, B. E. R.; Kneebone, J. L.; Neidig, M. L. A Combined Mössbauer, Magnetic Circular Dichroism, and Density Functional Theory Approach for Iron Cross-Coupling Catalysis: Electronic Structure, in Situ Formation, and Reactivity of Iron-Mesityl-Bisphosphines. J. Am. Chem. Soc. 2014, 136, 9132–9143. DOI: 10.1021/ja503596m.
   PubMed Web of Science ®Google Scholar
• Kneebone, J. L.; Brennessel, W. W.; Neidig, M. L. Intermediates and Reactivity in Iron-Catalyzed Cross-Couplings of Alkynyl Grignards with Alkyl Halides. J. Am. Chem. Soc. 2017, 139, 6988–7003. DOI: 10.1021/jacs.7b02363.
   PubMed Web of Science ®Google Scholar
• Jin, M.; Adak, L.; Nakamura, M. Iron-Catalyzed Enantioselective Cross-Coupling Reactions of α-Chloroesters with Aryl Grignard Reagents. J. Am. Chem. Soc. 2015, 137, 7128–7134. DOI: 10.1021/jacs.5b02277.
   PubMed Web of Science ®Google Scholar
• For a Review on Transition-Metal-Catalyzed Asymmetric Cross-Coupling Reactions, See: Cherney, A. H.; Kadunce, N. T.; Reisman, S. E. Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents to Construct C–C Bonds. Chem. Rev. 2015, 115, 9587–9652. DOI: 10.1021/acs.chemrev.5b00162.
   PubMed Web of Science ®Google Scholar
• Choi, J.; Fu, G. C. Transition Metal–Catalyzed Alkyl-Alkyl Bond Formation: Another Dimension in Cross-Coupling Chemistry. Science. 2017, 356, 152–160. DOI: 10.1126/science.aaf7230.
   Web of Science ®Google Scholar
• Mao, J.; Liu, F.; Wang, M.; Wu, L.; Zheng, B.; Liu, S.; Zhong, J.; Bian, Q.; Walsh, P. J. Cobalt–Bisoxazoline-Catalyzed Asymmetric Kumada Cross-Coupling of Racemic α-Bromo Esters with Aryl Grignard Reagents. J. Am. Chem. Soc. 2014, 136, 17662–17668. DOI: 10.1021/ja5109084.
   PubMed Web of Science ®Google Scholar
• For Reviews on Exploration of Mechanism of Iron-Catalyzed Cross-Coupling Reactions, See: (A) Parchomyk, T.; Koszinowski, K. Iron-Catalyzed Cross-Coupling: Mechanistic Insight for Rational Applications in Synthesis. Synthesis. 2017, 49, 3269–3280. DOI: 10.1055/s-0036-1588428. (b) Bedford, R. B. How Low Does Iron Go? Chasing the Active Species in Fe-Catalyzed Cross-Coupling Reactions. Acc. Chem. Res. 2015, 48, 1485–1493. DOI: 10.1021/acs.accounts.5b00042. (c) Mako, T. L.; Byers, J. A. Recent advances in iron-catalysed cross coupling reactions and their mechanistic underpinning. Inorg. Chem. Front. 2016, 3, 766–790. DOI: 10.1039/C5QI00295H. (d) Hedström, A.; Izakian, Z.; Vreto, I.; Wallentin, C.; Norrby, P. On the Radical Nature of Iron‐Catalyzed Cross‐Coupling Reactions. Chem. Eur. J. 2015, 21, 5946–5953. DOI: 10.1002/chem.201406096. (e) Cassani, C.; Bergonzini, G.; Wallentin, C. Active Species and Mechanistic Pathways in Iron-Catalyzed C–C Bond-Forming Cross-Coupling Reactions. ACS Catal. 2016, 6, 1640–1648. DOI: 10.1021/acscatal.5b02441.
   Web of Science ®Google Scholar
• Lee, W.; Zhou, J.; Gutierrez, O. Mechanism of Nakamura’s Bisphosphine-Iron-Catalyzed Asymmetric C(sp2)–C(sp3) Cross-Coupling Reaction: The Role of Spin in Controlling Arylation Pathways. J. Am. Chem. Soc. 2017, 139, 16126–16133. DOI: 10.1021/jacs.7b06377.
   PubMed Web of Science ®Google Scholar
• Sharma, A. K.; Sameera, W. M. C.; Jin, M.; Adak, L.; Okuzono, C.; Iwamoto, T.; Kato, M.; Nakamura, M.; Morokuma, K. DFT and AFIR Study on the Mechanism and the Origin of Enantioselectivity in Iron-Catalyzed Cross-Coupling Reactions. J. Am. Chem. Soc. 2017, 139, 16117–16125. DOI: 10.1021/jacs.7b05917.
   PubMed Web of Science ®Google Scholar
• Czaplik, W. M.; Mayer, M.; Cvengroš, J.; von Wangelin, A. Coming of Age: Sustainable Iron‐Catalyzed Cross‐Coupling Reactions. J. ChemSusChem. 2009, 2, 396–417. DOI: 10.1002/cssc.200900055.
   PubMed Web of Science ®Google Scholar
• Hedström, A.; Lindstedt, E.; Norrby, P. On the Oxidation State of Iron in Iron-Mediated C–C Couplings. J. Organomet. Chem. 2013, 748, 51–55. DOI: 10.1016/j.jorganchem.2013.04.024.
   Web of Science ®Google Scholar
• Bedford, R. B.; Brenner, P. B.; Carter, E.; Clifton, J.; Cogswell, P. M.; Gower, N. J.; Haddow, M. F.; Harvey, J. N.; Kehl, J. A.; Murphy, D. M.; et al. Iron Phosphine Catalyzed Cross-Coupling of Tetraorganoborates and Related Group 13 Nucleophiles with Alkyl Halides. Organometallics. 2014, 33, 5767–5780. DOI: 10.1021/om500518r.
   Web of Science ®Google Scholar
• Huang, Z.; Jin, L.; Feng, Y.; Peng, P.; Yi, H.; Lei, A. Iron‐Catalyzed Oxidative Radical Cross‐Coupling/Cyclization between Phenols and Olefins. Angew. Chem. Int. Ed. 2013, 52, 7151–7155. DOI: 10.1002/ange.201210023.
   PubMed Web of Science ®Google Scholar
• Ma, Y.; Zhang, D.; Yan, Z.; Wang, M.; Bian, C.; Gao, X.; Bunel, E. E.; Lei, A. Iron-Catalyzed Oxidative C–H/C–H Cross-Coupling between Electron-Rich Arenes and Alkenes. Org. Lett. 2015, 17, 2174–2177. DOI: 10.1021/acs.orglett.5b00775.
   PubMed Web of Science ®Google Scholar
• Muñoz, S. B., III; Daifuku, S. L.; Brennessel, W. W.; Neidig, M. L. Isolation, Characterization, and Reactivity of Fe8Me12 –: Kochi’S S = 1/2 Species in Iron-Catalyzed Cross-Couplings with MeMgBr and Ferric Salts. J. Am. Chem. Soc. 2016, 138, 7492–7495. DOI: 10.1021/jacs.6b03760.
   PubMed Web of Science ®Google Scholar
• Carpenter, S. H.; Neidig, M. L. A Physical‐Inorganic Approach for the Elucidation of Active Iron Species and Mechanism in Iron‐Catalyzed Cross‐Coupling. Isr. J. Chem. 2017, 57, 1106–1116. DOI: 10.1002/ijch.201700036.
   PubMed Web of Science ®Google Scholar
• Wunderlich, S. H.; Knochel, P. Preparation of Functionalized Aryl Iron(II) Compounds and a Nickel‐Catalyzed Cross‐Coupling with Alkyl Halides. Angew. Chem. Int. Ed. 2009, 48, 9717–9720. DOI: 10.1002/anie.200905196.
   PubMed Web of Science ®Google Scholar
• Meyer, S.; Orben, C. M.; Demeshko, S.; Dechert, S.; Meyer, F. Synthesis and Characterization of Di- and Tetracarbene Iron(II) Complexes with Chelating N-Heterocyclic Carbene Ligands and Their Application in Aryl Grignard–Alkyl Halide Cross-Coupling. Organometallics. 2011, 30, 6692–6702. DOI: 10.1021/om200870w.
   Web of Science ®Google Scholar
• Trage, C.; Schröder, D.; Schwarz, H. Coordination of Iron(III) Cations to β‐Keto Esters as Studied by Electrospray Mass Spectrometry: Implications for Iron‐Catalyzed Michael Addition Reactions. Chem. Eur. J. 2005, 11, 619–627. DOI: 10.1002/chem.200400715.
   PubMed Web of Science ®Google Scholar
• Parchomyk, T.; Koszinowski, K. Ate Complexes in Iron‐Catalyzed Cross‐Coupling Reactions. Chem. Eur. J. 2016, 22, 15609–15613. DOI: 10.1002/chem.201603574.
   PubMed Web of Science ®Google Scholar
• Bedford, R. B.; Brenner, P. B.; Elorriaga, D.; Harvey, J. N.; Nunn, J. The Influence of the Ligand Chelate Effect on Iron-Amine-Catalysed Kumada Cross-Coupling. Dalton Trans. 2016, 45, 15811–15817. DOI: 10.1039/c6dt01823h.
   PubMed Web of Science ®Google Scholar
• Bedford, R. B.; Brenner, P. B.; Carter, E.; Cogswell, P. M.; Haddow, M. F.; Harvey, J. N.; Murphy, D. M.; Nunn, J.; Woodall, C. H. TMEDA in Iron‐Catalyzed Kumada Coupling: Amine Adduct versus Homoleptic “Ate” Complex Formation. Angew. Chem. Int. Ed. 2014, 53, 1804–1808. DOI: 10.1002/anie.201308395.
   PubMed Web of Science ®Google Scholar
• Noda, D.; Sunada, Y.; Hatakeyama, T.; Nakamura, M.; Nagashima, H. Effect of TMEDA on Iron-Catalyzed Coupling Reactions of ArMgX with Alkyl Halides. J. Am. Chem. Soc. 2009, 131, 6078–6079. DOI: 10.1021/ja901262g.
   PubMed Web of Science ®Google Scholar
• Fürstner, A.; Martin, R.; Krause, H.; Seidel, G.; Goddard, R.; Lehmann, C. W. Preparation, Structure, and Reactivity of Nonstabilized Organoiron Compounds. Implications for Iron-Catalyzed Cross Coupling Reactions. J. Am. Chem. Soc. 2008, 130, 8773–8787. DOI: 10.1021/ja801466t.
   PubMed Web of Science ®Google Scholar
• Hohenberg, P.; Kohn, W. Inhomogeneous Electron Gas. Phys. Rev. 1964, 136, B864–B871. DOI: 10.1103/PhysRev.136.B864.
   Web of Science ®Google Scholar
• Kohn, W.; Sham, L. J. Self-Consistent Equations Including Exchange and Correlation Effects. Phys. Rev. 1965, 140, A1133–A1138. DOI: 10.1103/PhysRev.140.A1133.
   Web of Science ®Google Scholar
• Parr, R. G. Density Functional Theory. Annu. Rev. Phys. Chem. 1983, 34, 631–656. DOI: 10.1146/annurev.pc.34.100183.003215. (b) Geerlings, P.; De Proft, F.; Langenaeker, W. Conceptual Density Functional Theory. Chem. Rev. 2003, 103, 1793–1873. DOI: 10.1021/cr990029p. (c) Sousa, S. F.; Fernandes, P. A.; Ramos, M. J. General Performance of Density Functionals. J. Phys. Chem. A 2007, 111, 10439–10452. DOI: 10.1021/jp0734474. (d) Cohen, A. J.; Mori-Sánchez, P.; Yang, W. Challenges for Density Functional Theory. Chem. Rev. 2012, 112, 289–320. DOI: 10.1021/cr200107z. (e) Jones, R. O. Density functional theory: Its origins, rise to prominence, and future. Rev. Mod. Phys. 2015, 87, 897–923. DOI: 10.1103/RevModPhys.87.897. (f) Mardirossian, N.; Head-Gordon, M. Thirty years of density functional theory in computational chemistry: an overview and extensive assessment of 200 density functionals. Mol. Phys. 2017, 115, 2315–2372. DOI: 10.1080/00268976.2017.1333644. (g) Cramer, C. J.; Truhlar, D. G. Density functional theory for transition metals and transition metal chemistry. Phys. Chem. Chem. Phys. 2009, 11, 10757–10816. DOI: 10.1039/b907148b. (h) Neese, F. A critical evaluation of DFT, including time-dependent DFT, applied to bioinorganic chemistry. J. Biol. Inorg. Chem. 2006, 11, 702–711. DOI: 10.1007/s00775-006-0138-1. (i) Neese, F. Prediction of molecular properties and molecular spectroscopy with density functional theory: From fundamental theory to exchange-coupling. Coord. Chem. Rev. 2009, 253, 526–563. DOI: 10.1016/j.ccr.2008.05.014.
   Web of Science ®Google Scholar
• Alberto, M. E.; Marino, T.; Russo, N.; Sicilia, E.; Toscano, M. The Performance of Density Functional Based Methods in the Description of Selected Biological Systems and Processes. Phys. Chem. Chem. Phys. 2012, 14, 14943–14953. DOI: 10.1039/c2cp41836c.
   PubMed Web of Science ®Google Scholar
• Peverati, R.; Truhlar, D. G. Quest for a Universal Density Functional: The Accuracy of Density Functionals across a Broad Spectrum of Databases in Chemistry and Physics. Philos. Trans. R. Soc. A. 2014, 372, 20120476. DOI: 10.1098/rsta.2012.0476.
   Web of Science ®Google Scholar
• Sun, J.; Remsing, R. C.; Zhang, Y.; Sun, Z.; Ruzsinszky, A.; Peng, H.; Yang, Z.; Paul, A.; Waghmare, U.; Wu, X.; et al. Accurate First-Principles Structures and Energies of Diversely Bonded Systems from an Efficient Density Functional. Nat. Chem. 2016, 8, 831–836. DOI: 10.1038/NCHEM.2535.
   PubMed Web of Science ®Google Scholar
• Bowman, D. N.; Jakubikova, E. Low-Spin versus High-Spin Ground State in Pseudo-Octahedral Iron Complexes. Inorg. Chem. 2012, 51, 6011–6019. DOI: 10.1021/ic202344w.
   PubMed Web of Science ®Google Scholar
• Pinter, B.; Chankisjijev, A.; Geerlings, P.; Harvey, J. N.; De Proft, F., Conceptual Insights into DFT Spin‐State Energetics of Octahedral Transition‐Metal Complexes through a Density Difference Analysis. Chem. Eur. J. 2018, 24, 5281–5292. DOI: 10.1002/chem.201704657.
   PubMed Web of Science ®Google Scholar
• Roemelt, M.; Maganas, D.; DeBeer, S.; Neese, F. A Combined DFT and Restricted Open-Shell Configuration Interaction Method Including Spin-Orbit Coupling: Application to Transition Metal L-Edge X-Ray Absorption Spectroscopy. J. Chem. Phys. 2013, 138, 204101. DOI: 10.1063/1.4804607.
   PubMed Web of Science ®Google Scholar
• Reiher, M.; Salomon, O.; Hess, B. A. Reparameterization of Hybrid Functionals Based on Energy Differences of States of Different Multiplicity. Theor. Chem. Acc. 2001, 107, 48–55. DOI: 10.1007/s00214-001-0300-3.
   Web of Science ®Google Scholar
• Salomon, O.; Reiher, M.; Hess, B. A. Assertion and Validation of the Performance of the B3LYP* Functional for the First Transition Metal Row and the G2 Test Set. J. Chem. Phys. 2002, 117, 4729–4737. DOI: 10.1063/1.1493179.
   Web of Science ®Google Scholar
• Reiher, M. Theoretical Study of the Fe(phen)2(NCS)2 Spin-Crossover Complex with Reparametrized Density Functionals. Inorg. Chem. 2002, 41, 6928–6935. DOI: 10.1021/ic025891l.
   PubMed Web of Science ®Google Scholar
• Görling, A. Orbital- and State-Dependent Functionals in Density-Functional Theory. J. Chem. Phys. 2005, 123, 062203. DOI: 10.1063/1.1904583.
   PubMed Web of Science ®Google Scholar
• Swart, M. Metal–Ligand Bonding in Metallocenes: Differentiation between Spin State, Electrostatic and Covalent Bonding. Inorg. Chim. Acta. 2007, 360, 179–189. DOI: 10.1016/j.ica.2006.07.073.
   Web of Science ®Google Scholar
• Swart, M. Accurate Spin-State Energies for Iron Complexes. J. Chem. Theory Comput. 2008, 4, 2057–2066. DOI: 10.1021/ct800277a.
   PubMed Web of Science ®Google Scholar
• Swart, M.; Groenhof, A. R.; Ehlers, A. W.; Lammertsma, K. Validation of Exchange−Correlation Functionals for Spin States of Iron Complexes. J. Phys. Chem. A. 2004, 108, 5479–5483. DOI: 10.1021/jp049043i.
   Web of Science ®Google Scholar
• Fouqueau, A.; Casida, M. E.; Daku, L. M. L.; Hauser, A.; Neese, F. Comparison of Density Functionals for Energy and Structural Differences between the High- [5t2g:(T2g)4(Eg)2][5t2g:(T2g)4(Eg)2] and Low- [1a1g:(T2g)6(Eg)0][1a1g:(T2g)6(Eg)0] Spin States of iron(II) Coordination Compounds. II. More Functionals and the Hexaminoferrous Cation, [Fe(Nh3)6]2+. J. Chem. Phys. 2005, 122, 044110. DOI: 10.1063/1.1839854.
   PubMed Web of Science ®Google Scholar
• Fouqueau, A.; Mer, S.; Casida, M. E.; Daku, L. M. L.; Hauser, A.; Mineva, T.; Neese, F. Comparison of Density Functionals for Energy and Structural Differences between the High- [5t2g:(T2g)4(Eg)2][5t2g: (T2g)4(Eg)2] and Low- [1a1g:(T2g)6(Eg)0][1a1g: (T2g)6(Eg)0] Spin States of the Hexaquoferrous Cation [Fe(H2o)6]2+. J. Chem. Phys. 2004, 120, 9473–9486. DOI: 10.1063/1.1710046.
   PubMed Web of Science ®Google Scholar
• Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields. J. Phys. Chem. 1994, 98, 11623–11627. DOI: 10.1021/j100096a001.
   Web of Science ®Google Scholar
• (A) Purvis, G. D., III; Bartlett, R. J. A Full Coupled‐Cluster Singles and Doubles Model: The Inclusion of Disconnected Triples. J. Chem. Phys. 1982, 76, 1910–1918. DOI: 10.1063/1.443164. (b) Klopper, W.; Noga, J.; Koch, H.; Helgaker, T. Multiple Basis Sets in Calculations of Triples Corrections in Coupled-Cluster Theory. Theor. Chem. Acc. 1997, 97, 164–176. DOI: 10.1007/s002140050250. (c) Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. A Fifth-Order Perturbation Comparison of Electron Correlation Theories. Chem. Phys. Lett. 1989, 157, 479–483. DOI: 10.1016/S0009-2614(89)87395-6.
   Web of Science ®Google Scholar
• (A) Andersson, K.; Malmqvist, P.-Å.; Roos, B. O.; Sadlej, A. J.; Wolinski, K. Second-Order Perturbation Theory with a CASSCF Reference Function. J. Phys. Chem. 1990, 94, 5483–5488. DOI: 10.1021/j100377a012. (b) Andersson, K.; Malmqvist, P.-Å.; Roos, B. O. Second‐Order Perturbation Theory with a Complete Active Space Self‐Consistent Field Reference Function. J. Chem. Phys. 1992, 96, 1218–1226. DOI: 10.1063/1.462209. (c) Andersson, K. Different Forms of the Zeroth-Order Hamiltonian in Second-Order Perturbation Theory with a Complete Active Space Self-Consistent Field Reference Function. Theor. Chim. Acta. 1995, 91, 31–46. DOI: 10.1063/1.462209.
   Web of Science ®Google Scholar
• Hay, P. J.; Wadt, W. R. Ab Initio Effective Core Potentials for Molecular Calculations. Potentials for K to Au Including the Outermost Core Orbitals. J. Chem. Phys. 1985, 82, 299–310. DOI: 10.1063/1.448975.
   Web of Science ®Google Scholar
• (A) Weeks, J. D.; Hazi, A.; Rice, S. A. On the Use of Pseudopotentials in the Quantum Theory of Atoms and Molecules. Adv. Chem. Phys. 1969, 16, 283–342. (b) Bardsley, J. N. Pseudopotentials in Atomic and Molecular Physics. Case Stud. At. Phys. 1974, 4, 299–368. DOI: 10.1016/b978-0-7204-0331-2.50009-3. (c) Krauss, M.; Stevens, W. J. Effective Potentials in Molecular Quantum Chemistry. Ann. Rev. Phys. Chem. 1984, 35, 357–385. DOI: 10.1146/annurev.pc.35.100184.002041. (d) von Szentpaly, L.; Fuentealba, P.; Preuss, H.; Stoll, H. Pseudopotential Calculations on Rb+2, Cs+2, RbH+, CsH+ and the Mixed Alkali Dimer Ions. Chem. Phys. Lett. 1982, 93, 555–559. DOI: 10.1016/0009-2614(82)83728-7. (e) Dolg, M.; Wedig, U.; Stoll, H.; Preuss, H. Energy-Adjusted Ab Initio Pseudopotentials for the First Row Transition Elements. J. Chem. Phys. 1987, 86, 866–872. DOI: 10.1063/1.452288.
   Google Scholar
• Becke, A. D. Density‐Functional Thermochemistry. III. The Role of Exact Exchange. J. Chem. Phys. 1993, 98, 5648–5652. DOI: 10.1063/1.464913. (b) Hertwig, R. H.; Koch, W. On the parameterization of the local correlation functional. What is Becke-3-LYP? Chem. Phys. Lett. 1997, 268, 345–351. DOI: 10.1016/S0009-2614(97)00207-8. (c) Lee, C. T.; Yang, W. T.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 1988, 37, 785–789. DOI: 10.1103/PhysRevB.37.785.
   Web of Science ®Google Scholar
• (A) Zhao, Y.; Truhlar, D. G. Density Functionals with Broad Applicability in Chemistry. Acc. Chem. Res. 2008, 41, 157–167. DOI: 10.1021/ar700111a. (b) Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals. Theor. Chem. Acc. 2008, 120, 215–241. DOI: 10.1007/s00214-007-0310-x.
   PubMed Web of Science ®Google Scholar
• Zhao, Y.; Truhlar, D. G. A New Local Density Functional for Main-Group Thermochemistry, Transition Metal Bonding, Thermochemical Kinetics, and Noncovalent Interactions. J. Chem. Phys. 2006, 125, 194101. DOI: 10.1063/1.2370993.
   PubMed Web of Science ®Google Scholar
• (A) Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple. Phys. Rev. Lett. 1996, 77, 3865–3868. DOI: 10.1103/PhysRevLett.78.1396. (b) Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple. Phys. Rev. Lett. 1997, 78, 1396–1396.DOI: 10.1103/PhysRevLett.78.1396.
   PubMed Web of Science ®Google Scholar
• (A) Ditchfield, R.; Hehre, W. J.; Pople, J. A. Self‐Consistent Molecular‐Orbital Methods. IX. An Extended Gaussian‐Type Basis for Molecular‐Orbital Studies of Organic Molecules. J. Chem. Phys. 1971, 54, 724–728. DOI: 10.1063/1.1674902. (b) Hehre, W. J.; Ditchfield, R.; Pople, J. A. Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules. J. Chem. Phys. 1972, 56, 2257–2261. DOI: 10.1063/1.1677527. (c) Hariharan, P. C.; Pople, J. A. The Influence of Polarization Functions on Molecular Orbital Hydrogenation Energies. Theor. Chem. Acc. 1973, 28, 213–222. DOI: 10.1007/BF00533485. (d) Hariharan, P. C.; Pople, J. A. Accuracy of AH n Equilibrium Geometries by Single Determinant Molecular Orbital Theory. Mol. Phys. 1974, 27, 209–214. DOI: 10.1080/00268977400100171. (e) Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; DeFrees, D. J.; Pople, J. A.; Gordan, M. S. Self‐Consistent Molecular Orbital Methods. XXIII. A Polarization‐Type Basis Set for Second‐Row Elements. J. Chem. Phys. 1982, 77, 3654–3665. DOI: 10.1063/1.444267. (f) Binning Jr., R. C.; Curtiss, L. A. Compact Contracted Basis Sets for Third‐Row Atoms: Ga–Kr. J. Comp. Chem. 1990, 11, 1206–1216.DOI: 10.1002/jcc.54111013.
   Web of Science ®Google Scholar
• (A) McLean, A. D.; Chandler, G. S. Contracted Gaussian Basis Sets for Molecular Calculations. I. Second Row Atoms, Z=11–18. J. Chem. Phys. 1980, 72, 5639–5648. DOI: 10.1063/1.438980. (b) Raghavachari, K.; Binkley, J. S.; Seeger, R.; Pople, J. A. Self‐Consistent Molecular Orbital Methods. XX. A Basis Set for Correlated Wave Functions. J. Chem. Phys. 1980, 72, 650–654. DOI: 10.1063/1.438955. (c) Blaudeau, J.-P.; McGrath, M. P.; Curtiss, L. A.; Radom, L. Extension of Gaussian-2 (G2) Theory to Molecules Containing Third-Row Atoms K and Ca. J. Chem. Phys. 1997, 107, 5016–5021. DOI: 10.1063/1.474865. (d) Wachters, A. J. H. Gaussian Basis Set for Molecular Wavefunctions Containing Third‐Row Atoms. J. Chem. Phys. 1970, 52, 1033–1036. DOI: 10.1063/1.1673095. (e) Hay, P. J. Gaussian Basis Sets for Molecular Calculations. The Representation of 3d Orbitals in Transition‐Metal Atoms. J. Chem. Phys. 1977, 66, 4377–4384. DOI: 10.1063/1.433731. (f) McGrath, M. P.; Radom, L. Extension of Gaussian‐1 (G1) Theory to Bromine‐Containing Molecules. J. Chem. Phys. 1991, 94, 511–516. DOI: 10.1063/1.460367.
   Web of Science ®Google Scholar
• Grimme, S. Accurate Description of Van Der Waals Complexes by Density Functional Theory Including Empirical Corrections. J. Comput. Chem. 2004, 25, 1463–1473. DOI: 10.1002/jcc.20078. (b) Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J. Chem. Phys. 2010, 132, 154104. DOI: 10.1063/1.3382344. (c) Grimme, S. Density functional theory with London dispersion corrections. WIRES Comput. Mol. Sci. 2011, 1, 211–228. DOI: 10.1002/wcms.30. (d) Ehrlich, S.; Moellmann, J.; Grimme, S. Dispersion-Corrected Density Functional Theory for Aromatic Interactions in Complex Systems. Acc. Chem. Res. 2012, 46, 916–926. DOI: 10.1021/ar3000844.
   PubMed Web of Science ®Google Scholar
• (A) Klamt, A.; Schüürmann, G. COSMO: A New Approach to Dielectric Screening in Solvents with Explicit Expressions for the Screening Energy and Its Gradient. J. Chem. Soc. Perkin Trans. 1993, 2, 799–805. DOI: 10.1039/P29930000799. (b) Tomasi, J.; Persico, M. Molecular Interactions in Solution: An Overview of Methods Based on Continuous Distributions of the Solvent. Chem. Rev. 1994, 94, 2027–2094. DOI: 10.1021/cr00031a013. (c) Andzelm, J.; Kölmel, C.; Klamt, A. Incorporation of Solvent Effects into Density Functional Calculations of Molecular Energies and Geometries. J. Chem. Phys. 1995, 103, 9312–9320. DOI: 10.1063/1.469990. (d) Barone, V.; Cossi, M. Quantum Calculation of Molecular Energies and Energy Gradients in Solution by a Conductor Solvent Model. J. Phys. Chem. A 1998, 102, 1995–2001. DOI: 10.1021/jp9716997. (e) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. Energies, Structures, and Electronic Properties of Molecules in Solution with the C‐PCM Solvation Model. J. Comput. Chem. 2003, 24, 669–681. DOI: 10.1002/jcc.10189.
   Google Scholar
• Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions. J. Phys. Chem. B. 2009, 113, 6378–6396. DOI: 10.1021/jp810292n.
   PubMed Web of Science ®Google Scholar
• (A) Runge, E.; Gross, E. K. U. Density-Functional Theory for Time-Dependent Systems. Phys. Rev. Lett. 1984, 52, 997–1000. DOI: 10.1103/PhysRevLett.52.997. (b) Gross, E. K. U.; Kohn, W. Time-Dependent Density-Functional Theory. Adv. Quantum Chem. 1990, 21, 255–291. DOI:10.1016/S0065-3276(08)60600-0. (c) van Leeuwen, R. Key Concepts in Time-Dependent Density-Functional Theory. Int. J. Mod. Phys. B 2001, 15, 1969–2023. DOI: 10.1142/S021797920100499X. (d) Onida, G.; Reining, L.; Rubio, A. Electronic Excitations: Density-Functional Versus Many-Body Green’s-Function Approaches. Rev. Mod. Phys. 2002, 74, 601–659. DOI: 10.1103/RevModPhys.74.601.
   Web of Science ®Google Scholar
• Fleischauer, V. E.; Muñoz, S. B., III; Neate, P. G. N.; Brennessel, W. W.; Neidig, M. L. NHC and Nucleophile Chelation Effects on Reactive iron(II) Species in Alkyl–Alkyl Cross-Coupling. Chem. Sci. 2018, 9, 1878–1891. DOI: 10.1039/c7sc04750a.
   PubMed Web of Science ®Google Scholar
• Muñoz, S. B., III; Daifuku, S. L.; Sears, J. D.; Baker, T. M.; Carpenter, S. H.; Brennessel, W. W.; Neidig, M. L. The N‐Methylpyrrolidone (NMP) Effect in Iron‐Catalyzed Cross‐Coupling with Simple Ferric Salts and MeMgBr. Angew. Chem. Int. Ed. 2018, 57, 6496–6500. DOI: 10.1002/ANIE.201802087.
   PubMed Web of Science ®Google Scholar
• Al-Afyouni, M. H.; Fillman, K. L.; Brennessel, W. W.; Neidig, M. L. Isolation and Characterization of a Tetramethyliron(III) Ferrate: An Intermediate in the Reduction Pathway of Ferric Salts with MeMgBr. J. Am. Chem. Soc. 2014, 136, 15457–15460. DOI: 10.1021/ja5080757.
   PubMed Web of Science ®Google Scholar
• Kneebone, J. L.; Fleischauer, V. E.; Daifuku, S. L.; Shaps, A. A.; Bailey, J. M.; Iannuzzi, T. E.; Neidig, M. L. Electronic Structure and Bonding in Iron(II) and Iron(I) Complexes Bearing Bisphosphine Ligands of Relevance to Iron-Catalyzed C–C Cross-Coupling. Inorg. Chem. 2016, 55, 272–282. DOI: 10.1021/acs.inorgchem.5b02263.
   PubMed Web of Science ®Google Scholar
• Fillman, K. L.; Przyojski, J. A.; Al-Afyouni, M. H.; Tonzetich, Z. J.; Neidig, M. L. A Combined Magnetic Circular Dichroism and Density Functional Theory Approach for the Elucidation of Electronic Structure and Bonding in Three- and Four-Coordinate iron(II)–N-heterocyclic Carbene Complexes. Chem. Sci. 2015, 6, 1178–1188. DOI: 10.1039/c4sc02791d.
   PubMed Web of Science ®Google Scholar
• Iannuzzi, T. E.; Gao, Y.; Baker, T. M.; Deng, L.; Neidig, M. L. Magnetic Circular Dichroism and Density Functional Theory Studies of Electronic Structure and Bonding in cobalt(II)–N-heterocyclic Carbene Complexes. Dalton Trans. 2017, 46, 13290–13299. DOI: 10.1039/c7dt01748k.
   PubMed Web of Science ®Google Scholar
• Hoyt, J. M.; Shevlin, M.; Margulieux, G. W.; Krska, S. W.; Tudge, M. T.; Chirik, P. J. Synthesis and Hydrogenation Activity of Iron Dialkyl Complexes with Chiral Bidentate Phosphines. Organometallics. 2014, 33, 5781–5790. DOI: 10.1021/om500329q.
   Web of Science ®Google Scholar
• Rousseau, L.; Brémond, E.; Lefèvre, G. Assessment of the Ground Spin State of iron(I) Complexes: Insights from DFT Predictive Models. New J. Chem. 2018, 42, 7612–7616. DOI: 10.1039/c7nj04816e.
   Web of Science ®Google Scholar
• Ehrlich, N.; Kreye, M.; Baabe, D.; Schweyen, P.; Freytag, M.; Jones, P. G.; Walter, M. D. Synthesis and Electronic Ground-State Properties of Pyrrolyl-Based Iron Pincer Complexes: Revisited. Inorg. Chem. 2017, 56, 8415–8422. DOI: 10.1021/acs.inorgchem.7b01078.
   PubMed Web of Science ®Google Scholar
• Holloway, L. R.; Clough, A. J.; Li, J. Y.; Tao, E. L.; Tao, F.; Li, L. A Combined Experimental and Theoretical Study of Dinitrosyl Iron Complexes Containing Chelating bis(diphenyl)phosphinoX (X = Benzene, Propane and Ethylene): X-Ray Crystal Structures and Properties Influenced by the Presence or Absence of π-bonds in Chelating Ligands. Polyhedron. 2014, 70, 29–38. DOI: 10.1016/j.poly.2013.12.019.
   PubMed Web of Science ®Google Scholar
• Roy, S.; Mazinani, S. K. S.; Groy, T. L.; Gan, L.; Tarakeshwar, P.; Mujica, V.; Jones, A. K. Catalytic Hydrogen Evolution by Fe(II) Carbonyls Featuring a Dithiolate and a Chelating Phosphine. Inorg. Chem. 2014, 53, 8919–8929. DOI: 10.1021/ic5012988.
   PubMed Web of Science ®Google Scholar
• Pascualini, M. E.; Stoian, S. A.; Ozarowski, A.; Abboud, K. A.; Veige, A. S. Solid State Collapse of a High-Spin Square-Planar Fe(II) Complex, Solution Phase Dynamics, and Electronic Structure Characterization of an Fe(II)2 Dimer. Inorg. Chem. 2016, 55, 5191–5200. DOI: 10.1021/acs.inorgchem.6b00075.
   PubMed Web of Science ®Google Scholar
• Pascualini, M. E.; Di Russo, N. V.; Thujis, A. E.; Ozarowski, A.; Stoian, S. A.; Abboud, K. A.; Christou, G.; Veige, A. S. A High-Spin Square-Planar Fe(II) Complex Stabilized by A Trianionic Pincer-Type Ligand and Conclusive Evidence for Retention of Geometry and Spin State in Solution. Chem. Sci. 2015, 6, 608–612. DOI: 10.1039/c4sc02634a.
   PubMed Web of Science ®Google Scholar
• Barreca, D.; Carraro, G.; Gasparotto, A.; Maccato, C.; Seraglia, R.; Tabacchi, G. An iron(II) Diamine Diketonate Molecular Complex: Synthesis, Characterization and Application in the CVD of Fe2O3 Thin Films. Inorg. Chim. Acta. 2012, 380, 161–166. DOI: 10.1016/j.ica.2011.10.036.
   Web of Science ®Google Scholar
• Schmidt, V. A.; Kennedy, C. R.; Bezdek, M. J.; Chirik, P. J. Selective [1,4]-Hydrovinylation of 1,3-Dienes with Unactivated Olefins Enabled by Iron Diimine Catalysts. J. Am. Chem. Soc. 2018, 140, 3443–3453. DOI: 10.1021/jacs.8b00245.
   PubMed Web of Science ®Google Scholar
• Baker, T. M.; Mako, T. L.; Vasilopoulos, A.; Li, B.; Byers, J. A.; Neidig, M. L. Magnetic Circular Dichroism and Density Functional Theory Studies of Iron(II)-Pincer Complexes: Insight into Electronic Structure and Bonding Effects of Pincer N-Heterocyclic Carbene Moieties. Organometallics. 2016, 35, 3692–3700. DOI: 10.1021/acs.organomet.6b00651.
   Web of Science ®Google Scholar
• (A) Hedstrom, A.; Lidstedt, E.; Norrby, P.-O. On the Oxidation State of Iron in Iron-Mediated C–C Couplings. J. Organomet. Chem. 2013, 748, 51–55. DOI: 10.1016/j.jorganchem.2013.04.024. (b) Ren, Q.; An, S.; Huang, Z.; Wu, N.; Shen, X. New Insights into the Mechanism of Iron-Catalyzed Cross-Coupling Reactions. J. Organomet. Chem. 2017, 844, 8–15. DOI: 10.1039/c4dt03491k. (c) Clémancey, M.; Cantat, T.; Blondin, G.; Latour, J.; Dorlet, P.; Lefèvre, G. Halogen Atom Transfer Mechanism of Iron-Catalyzed Direct Arylation to Form Biaryl Using Density Functional Theory calculations. Inorg. Chem. 2017, 56, 3834–3848. DOI: 10.1016/j.jorganchem.2017.05.035. (d) Structural Insights into the Nature of Fe0 and FeI Low-Valent Species Obtained upon the Reduction of Iron Salts by Aryl Grignard Reagents. DOI: 10.1021/acs.inorgchem.6b02616.
   Web of Science ®Google Scholar
• Chen, Z.; Zhang, D.; Jin, Y.; Yang, Y.; Su, N. Q.; Yang, W. Multireference Density Functional Theory with Generalized Auxiliary Systems for Ground and Excited States. J. Phys. Chem. Lett. 2017, 8, 4479–4485. DOI: 10.1021/acs.jpclett.7b01864.
   PubMed Web of Science ®Google Scholar
• Schröder, D.; Shaik, S.; Schwarz, H. Two-State Reactivity as a New Concept in Organometallic Chemistry. Acc. Chem. Res. 2000, 33, 139–145. DOI: 10.1021/ar990028j.
   PubMed Web of Science ®Google Scholar