Copper-catalyzed cyanoisopropylation of beta-keto esters using azos: synthesis of beta-dicarbonyls bearing an alfa-tertiary nitrile moiety

References

• (a) Hu, P.; Chai, J.; Duan, Y.; Liu, Z.; Cui, G.; Chen, L. Progress in Nitrile-Based Polymer Electrolytes for High Performance Lithium Batteries. J. Mater. Chem. A 2016, 4, 10070-10083. DOI: 10.1039/C6TA02907H(b) Miller, J. S.; Manson, J. L. Designer Magnets Containing Cyanides and Nitriles. Acc. Chem. Res. 2001, 34, 563-570. DOI: 10.1021/ar0000354.
   Web of Science ®Google Scholar
• (a) Fleming, F. F.; Yao, L.; Ravikumar, P. C.; Funk, L.; Shook, B. C. Nitrile-Containing Pharmaceuticals: Efficacious Roles of the Nitrile Pharmacophore. J. Med. Chem. 2010, 53, 7902-7917. DOI: 10.1021/jm100762r. (b) Fleming, F. F. Nitrile-Containing Natural Products. Nat. Prod. Rep. 1999, 16, 597-606. DOI: 10.1039/A804370A.
   PubMed Web of Science ®Google Scholar
• Elnagdi, M. H.; Sherif, S. M.; Mohareb, R. M. The Synthetic Potentialities of Nitriles in Heterocyclic Synthesis. Heterocycles 1987, 26, 497-536. DOI: 10.3987/R-1987-02-0497.
   Web of Science ®Google Scholar
• (a) You, X.; Xie, X.; Wang, G.; Xiong, M.; Sun, R.; Chen, H.; Liu, Y. Nickel‐Catalyzed [2 + 2 + 2] Cycloaddition of Alkyne‐Nitriles with Alkynes Assisted by Lewis Acids: Efficient Synthesis of Fused Pyridines. Chem. Eur. J. 2016, 22, 16765-16769. DOI: 10.1002/chem.201603829. (b) Varelas, J. G.; Khanal, S.; O'Donnell, M. A.; Mulcahy, S. P. Concise Synthesis of Annulated Pyrido[3,4-b]indoles via Rh(I)-Catalyzed Cyclization. Org. Lett. 2015, 17, 5512-5514. DOI: 10.1021/acs.orglett.5b02807. (c) Azab, M. E.; Rizk, S. A.; Amr, A. E. E. Synthesis of Some Novel Heterocyclic and Schiff Base Derivatives as Antimicrobial Agents. Molecules 2015, 20, 18201−18218. DOI: 10.3390/molecules201018201. (d) Xia, G.; Han, X.; Lu, X. Pd(II)-Catalyzed One-Step Construction of Cycloalkane-Fused Indoles and Its Application in Formal Synthesis of (±)-Aspidospermidine. Org. Lett. 2014, 16, 2058-2061. DOI: 10.1021/ol500662f. (e) D'Souza, B. R.; Lane, T. K.; Louie, J. Iron-Catalyzed Cycloaddition of Alkynenitriles and Alkynes. Org. Lett. 2011, 13, 2936-2939. DOI: 10.1021/ol2009939. (f) Garcia, P.; Moulin, S.; Miclo, Y.; Leboeuf, D.; Gandon, V.; Aubert, C.; Malacria, M. Synthesis of Tricyclic Fused 3‐Aminopyridines Through Intramolecular CoI‐Catalyzed [2 + 2+2] Cycloaddition Between Ynamides, Nitriles, and Alkynes. Chem. Eur. J. 2009, 15, 2129-2139. DOI: 10.1002/chem.200802301.
   PubMed Web of Science ®Google Scholar
• (a) Wang, B.; Xue, P.; Gu, P. Intramolecular Schmidt Reaction of Acyl Chlorides with Alkyl Azides: Preparation of Pyrrolizine by Intramolecular Capture of Intermediates with Alkenes or Alkynes. Chem. Commun. 2015, 51, 2277-2279. DOI: 10.1039/C4CC07166B. (b) Yu, Z.; Brannigan, J. A.; Rangachari, K.; Heal, W. P.; Wilkinson, A. J.; Holder, A. A.; Leatherbarrow, R. J.; Tate, E. W. Discovery of Pyridyl-based Inhibitors of Plasmodium falciparum N-myristoyltransferase. Med. Chem. Commun. 2015, 6, 1767-1772. DOI: 10.1039/C5MD00242G. (c) Streuff, J.; Feurer, M.; Bichovski, P.; Frey, G.; Gellrich, U. Enantioselective Titanium(III)‐Catalyzed Reductive Cyclization of Ketonitriles. Angew. Chem. Int. Ed. 2012, 51, 8661-8664. DOI: 10.1002/anie.201204469.
   PubMed Web of Science ®Google Scholar
• (a) Zhou, J.; Yu, G.; Huang, F. Supramolecular Chemotherapy Based on Host-Guest Molecular Recognition: A Novel Strategy in the Battle Against Cancer with a Bright Future. Chem. Soc. Rev. 2017, 46, 7021-7053. DOI: 10.1039/C6CS00898D. (b) Stoffelen, C.; Huskens, J. Soft Supramolecular Nanoparticles by Noncovalent and Host-Guest Interactions. Small 2016, 12, 96-119. DOI: 10.1002/smll.201501348. (c) Wei, P.; Yan, X.; Huang, F. Supramolecular Polymers Constructed by Orthogonal Self-Assembly Based on Host-Guest and Metal-Ligand Interactions. Chem. Soc. Rev. 2015, 44, 815-832. DOI: 10.1039/C4CS00327F.
   PubMed Web of Science ®Google Scholar
• (a) Demir, A. S.; Emrullahoglu, M. An Effective New Synthesis of 2-Aminopyrrole-4-Carboxylates. Tetrahedron 2005, 61, 10482-10489. DOI: 10.1016/j.tet.2005.08.050. (b) Michael, J. P.; de Koning, C. B.; van der Westhuyzen, C. W.; Fernandes, M. A. Influence of Ring Size on the Outcome of Sulfide Contraction Reactions with Thiolactams. Isolation of Bicyclic Ketene S,N-acetals and Thioisomünchnones. J. Chem. Soc. Perkin Trans. 1 2001, 2055-2062. DOI: 10.1039/B103560F.
   Web of Science ®Google Scholar
• Wang, C.; Li, Y.; Gong, M.; Wu, Q.; Zhang, J.; Kim, J. K.; Huang, M.; Wu, Y. Method for Direct Synthesis of α-Cyanomethyl-β-Dicarbonyl Compounds with Acetonitrile and 1,3-Dicarbonyls. Org. Lett. 2016, 18, 4151-4153. DOI: 10.1021/acs.orglett.6b01871.
   PubMed Web of Science ®Google Scholar
• (a) Chu, X.; Ge, D.; Shen, Z.; Loh, T. Recent Advances in Radical-Initiated C(sp3)-H Bond Oxidative Functionalization of Alkyl Nitriles. ACS Catal. 2018, 8, 258-271. DOI: 10.1021/acscatal.7b03334. (b) López, R.; Palomo, C. Cyanoalkylation: Alkylnitriles in Catalytic C-C Bond‐Forming Reactions. Angew. Chem. Int. Ed. 2015, 54, 13170-13184. DOI: 10.1002/anie.201502493.
   Web of Science ®Google Scholar
• (a) Li, Y.; Chang, Y.; Li, Y.; Cao, C.; Yang, J.; Wang, B.; Liang, D. Iron-Catalyzed exo-Selective Synthesis of Cyanoalkyl Indolines via Cyanoisopropylarylation of Unactivated Alkenes. Adv. Synth. Catal. 2018, 360, 2488-2492. DOI: 10.1002/adsc.201800296. (b) Liang, D.; Dong, Q.; Xu, P.; Dong, Y.; Li, W.; Ma, Y. Synthesis of CF3CH2-Containing Indolines by Transition-Metal-Free Aryltrifluoromethylation of Unactivated Alkenes. J. Org. Chem. 2018, 83, 11978−11986. DOI: 10.1021/acs.joc.8b01861. (c) Liang, D.; Ge, D.; Lv, Y.; Huang, W.; Wang, B.; Li, W. Silver-Catalyzed Radical Arylphosphorylation of Unactivated Alkenes: Synthesis of 3-Phosphonoalkyl Indolines. J. Org. Chem. 2018, 83, 4681−4691. DOI: 10.1021/acs.joc.8b00450. (d) Liang, D.; Li, Y.; Gao, S.; Li, R.; Li, X.; Wang, B.; Yang, H. Amide-Assisted Radical Strategy: Metal-Free Direct Fluorination of Arenes in Aqueous Media. Green Chem. 2017, 19, 3344-3349. DOI: 10.1039/c7gc00356k. (e) Liang, D.; Li, X.; Lan, Q.; Huang, W.; Yuan, L.; Ma, Y. Tin Tetrachloride Pentahydrate-Catalyzed Regioselective Chlorohydroxylation of α,β-Unsaturated Ketones in Water with Selectfluor as a Chlorine Source. Tetrahedron Lett. 2016, 57, 2207-2210. DOI: 10.1016/j.tetlet.2016.04.028.
   Web of Science ®Google Scholar
• (a) Li, Y.; Liang, D.; Chang, Y.; Li, X.; Fu, S.; Yuan, Y.; Wang, B. Metal-Free and Selective Cleavage of Unstrained Carbon-Carbon Single Bonds: Synthesis of β-Ketosulfones from β-Chlorohydrins and Sodium Sulfinates. Synth. Commun. 2017, 47, 2044-2052. DOI: 10.1080/00397911.2017.1362439. (b) Li, Y.; Liang, D.; Li, X.; Huang, W.; Yuan, L.; Wang, B.; Cheng, P. Br2- or HBr-Catalyzed Synthesis of Asymmetric 3,3-Di(indolyl)indolin-2-ones. Heterocycl. Commun. 2017, 23, 29-34. DOI: 10.1515/hc-2016-0071. (c) Liang, D.; Li, X.; Wang, C.; Dong, Q.; Wang, B.; Wang, H. Regioselective and Efficient Bromination of Anilides on Water Using HBr and Selectfluor. Tetrahedron Lett. 2016, 57, 5390-5394. DOI: 10.1016/j.tetlet.2016.10.092. (d) Liang, D.; Li, X.; Zhang, W.; Li, Y.; Zhang, M.; Cheng, P. Br2 as a Novel Lewis Acid Catalyst for Friedel-Crafts Alkylation of Indoles with α,β-Unsaturated Ketones. Tetrahedron Lett. 2016, 57, 1027-1030. DOI: 10.1016/j.tetlet.2016.01.078. (e) Liang, D.; Li, X.; Li, Y.; Yang, Y.; Gao, S.; Cheng, P. Br2-Catalyzed Regioselective Dehydrative Coupling of Indoles with Acyloins: Direct Synthesis of α-(3-Indolyl) Ketones. RSC Adv. 2016, 6, 29020-29025. DOI: 10.1039/c6ra03321k.
   Web of Science ®Google Scholar
• Krys, P.; Matyjaszewski, K. Kinetics of Atom Transfer Radical Polymerization. Eur. Polym. J. 2017, 89, 482-523. DOI: 10.1016/j.eurpolymj.2017.02.034.
   Web of Science ®Google Scholar
• Studer, A.; Curran, D. P. Catalysis of Radical Reactions: A Radical Chemistry Perspective. Angew. Chem. Int. Ed. 2016, 55, 58-102. DOI: 10.1002/anie.201505090.
   PubMed Web of Science ®Google Scholar
• (a) Tang, S.; Liu, Y.; Gao, X.; Wang, P.; Huang, P.; Lei, A. Multi-Metal-Catalyzed Oxidative Radical Alkynylation with Terminal Alkynes: A New Strategy for C(sp3)-C(sp) Bond Formation. J. Am. Chem. Soc. 2018, 140, 6006-6013. DOI: 10.1021/jacs.8b02745. (b) Zhang, X.; Huang, H. Copper-Catalyzed Oxidative Coupling of AIBN and Ketone-Derived Enoxysilanes to γ-Ketonitriles. Org. Lett. 2018, 20, 4998-5001. DOI: 10.1021/acs.orglett.8b02154. (c) Irudayanathan, F. M.; Lee, S. Selective Synthesis of (E)- and (Z)-Allyl Nitriles via Decarboxylative Reactions of Alkynyl Carboxylic Acids with Azobis(Alkylcarbonitriles). Org. Lett. 2017, 19, 2318-2321. DOI: 10.1021/acs.orglett.7b00860. (d) Liu, B.; Wang, C.; Hu, M.; Song, R.; Chen, F.; Li, J. Copper-promoted [2 + 2+2] Annulation of 1,n-Enynes Through Decomposition of Azobis(alkyl nitrile)S. Chem. Commun. 2017, 53, 1265-1268. DOI: 10.1039/C6CC09063J. (e) Song, W.; Yan, P.; Shen, D.; Chen, Z.; Zeng, X.; Zhong, G. Synthesis of Cyano-Containing Phenanthridine Derivatives via Catalyst-, Base-, and Oxidant-Free Direct Cyanoalkylarylation of Isocyanides. J. Org. Chem. 2017, 82, 4444-4448. DOI: 10.1021/acs.joc.7b00343. (f) Lan, X.; Wang, N.; Bai, C.; Lan, C.; Zhang, T.; Chen, S.; Xing, Y. Unactivated C(sp3)-H Bond Functionalization of Alkyl Nitriles with Vinylarenes and Mechanistic Studies, Org. Lett. 2016, 18, 5986-5989. DOI: 10.1021/acs.orglett.6b02692. (g) Leifert, D.; Artiukhin, D. G.; Neugebauer, J.; Galstyan, A.; Strassert, C. A.; Studer, A. Radical Perfluoroalkylation-Easy Access to 2-Perfluoroalkylindol-3-imines via Electron Catalysis. Chem. Commun. 2016, 52, 5997-6000. DOI: 10.1039/C6CC02284G. (h) Deng, Y.; Tang, S.; Ding, G.; Wang, M.; Li, J.; Li, Z.; Yuan, L.; Sheng, R. Radical-Mediated Divergent Cyclization of Benzamides Toward Perfluorinated or Cyanated Isoquinolinediones. Org. Biomol. Chem. 2016, 14, 9348-9353. DOI: 10.1039/C6OB01550F. (i) Wei, W.; Wen, J.; Yang, D.; Guo, M.; Tian, L.; You, J.; Wang, H. Copper-Catalyzed Cyanoalkylarylation of Activated Alkenes with AIBN: A Convenient and Efficient Approach to Cyano-Containing Oxindoles. RSC Adv. 2014, 4, 48535-48538. DOI: 10.1039/C4RA09022E.
   PubMed Web of Science ®Google Scholar
• Roberts, B. P. Polarity-Reversal Catalysis of Hydrogen-Atom Abstraction Reactions: Concepts and Applications in Organic Chemistry. Chem. Soc. Rev. 1999, 28, 25-35. DOI: 10.1039/a804291h.
   Web of Science ®Google Scholar
• (a) Hu, A.; Guo, J.; Pan, H.; Zuo, Z. Selective Functionalization of Methane, Ethane, and Higher Alkanes by Cerium Photocatalysis. Science 2018, 361, 668-672. DOI: 10.1126/science.aat9750. (b) Trowbridge, A.; Reich, D.; Gaunt, M. J. Multicomponent Synthesis of Tertiary Alkylamines by Photocatalytic Olefin-hydroaminoalkylation. Nature 2018, 561, 522-527. DOI: 10.1038/s41586-018-0537-9. (c) Guo, X.; Wenger, O. S. Reductive Amination by Photoredox Catalysis and Polarity-Matched Hydrogen Atom Transfer. Angew. Chem. Int. Ed. 2018, 57, 2469-2473; DOI: 10.1002/anie.201711467. (d) Le, C.; Liang, Y.; Evans, R. W.; Li, X.; MacMillan, D. W. C. Selective sp3 C-H Alkylation via Polarity-Matchbased Cross-Coupling. Nature 2017, 547, 79−83. DOI: 10.1038/nature22813.
   PubMed Web of Science ®Google Scholar