Glycinamide hydrochloride as a transient directing group: Synthesis of 2-benzylbenzaldehydes by C(sp³)−H arylation

References

• Chen, X. Y.; Ozturk, S.; Sorensen, E. J. Pd-Catalyzed Ortho C–H Hydroxylation of Benzaldehydes Using a Transient Directing Group. Org. Lett. 2017, 19, 6280–6283. DOI: 10.1021/acs.orglett.7b02906.
   PubMed Web of Science ®Google Scholar
• Zhao, Q.; Poisson, T.; Pannecoucke, X.; Besset, T. The Transient Directing Group Strategy: A New Trend in Transition-Metal-Catalyzed C–H Bond Functionalization. Synthesis 2017, 49, 4808–4826. DOI: 10.1055/s-0036-1590878.
   Web of Science ®Google Scholar
• Gandeepan, P.; Ackermann, L. Transient Directing Groups for Transformative C–H Activation by Synergistic Metal Catalysis. Chem 2018, 4, 199–222. DOI: 10.1016/j.chempr.2017.11.002.
   Web of Science ®Google Scholar
• Chen, X. Y.; Sorensen, E. J. Pd-Catalyzed, Ortho C–H Methylation and Fluorination of Benzaldehydes Using Orthanilic Acids as Transient Directing Groups. J. Am. Chem. Soc. 2018, 140, 2789–2792. DOI: 10.1021/jacs.8b00048.
   PubMed Web of Science ®Google Scholar
• Hu, X. X.; Liu, J. B.; Wang, L. L.; Huang, F.; Sun, C. Z.; Chen, D. Z. The Stabilizing Effect of the Transient Imine Directing Group in the Pd(II)-Catalyzed C(sp3)–H Arylation of Free Primary Amines. Org. Chem. Front. 2018, 5, 1670–1678. DOI: 10.1039/C8QO00094H.
   Web of Science ®Google Scholar
• Xu, J.; Liu, Y.; Zhang, J.; Xu, X.; Jin, Z. Palladium-Catalyzed Enantioselective C(sp2)-H arylation of ferrocenyl ketones enabled by a chiral transient directing group. Chem. Commun. (Camb.) 2018, 54, 689–692. DOI: 10.1039/C7CC09273C.
   PubMed Web of Science ®Google Scholar
• Niu, B.; Yang, K.; Lawrence, B.; Ge, H. Transient Ligand-Enabled Transition Metal-Catalyzed C–H Functionalization. ChemSusChem 2019, 12, 2955–2969. DOI: 10.1002/cssc.201900151.
   PubMed Web of Science ®Google Scholar
• Huang, J.; Ding, J.; Ding, T. M.; Zhang, S.; Wang, Y.; Sha, F.; Zhang, S. Y.; Wu, X. Y.; Li, Q. Cobalt-Catalyzed Ortho-C(sp2)-H Amidation of Benzaldehydes with Dioxazolones Using Transient Directing Groups. Org. Lett. 2019, 21, 7342–7345. DOI: 10.1021/acs.orglett.9b02632.
   PubMed Web of Science ®Google Scholar
• Qiao, H.; Sun, B.; Yu, Q.; Huang, Y. Y.; Zhou, Y.; Zhang, F. L. Palladium-Catalyzed Direct Ortho-C–H Selenylation of Benzaldehydes Using Benzidine as a Transient Directing Group. Org. Lett. 2019, 21, 6914–6918. DOI: 10.1021/acs.orglett.9b02530.
   PubMedGoogle Scholar
• Shang, Y.; Jonnada, K.; Yedage, S. L.; Tu, H.; Zhang, X.; Lou, X.; Huang, S.; Su, W. Rhodium(III)-Catalyzed Indole Synthesis at Room Temperature Using the Transient Oxidizing Directing Group Strategy. Chem. Commun. 2019, 55, 9547–9550. DOI: 10.1039/C9CC04529E.
   PubMedGoogle Scholar
• Wang, Y. F.; Xu, W. G.; Sun, B.; Yu, Q. Q.; Li, T. J.; Zhang, F. L. Monodentate Transient Directing Group Assisted Pd-Catalyzed Direct Dehydrogenative Cross-Coupling of Benzaldehydes with Arenes toward 9-Fluorenones. J. Org. Chem. 2019, 84, 13104–13111. DOI: 10.1021/acs.joc.9b02139.
   PubMed Web of Science ®Google Scholar
• Guan, Z.; Chen, S.; Huang, Y.; Yao, H. Rhodium(III)-Catalyzed Intramolecular Olefin Hydroarylation of Aromatic Aldehydes Using a Transient Directing Group. Org. Lett. 2019, 21, 3959–3962. DOI: 10.1021/acs.orglett.9b01101.
   PubMed Web of Science ®Google Scholar
• Li, F.; Zhou, Y.; Yang, H.; Wang, Z.; Yu, Q.; Zhang, F. L. Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C–H Methoxylation and Chlorination of Benzaldehydes. Org. Lett. 2019, 21, 3692–3965. DOI: 10.1021/acs.orglett.9b01158.
   PubMed Web of Science ®Google Scholar
• Zhang, X. L.; Pan, G. F.; Zhu, X. Q.; Guo, R. L.; Gao, Y. R.; Wang, Y. Q. Dehydrogenative β-Arylation of Saturated Aldehydes Using Transient Directing Groups. Org. Lett. 2019, 21, 2731–2735. DOI: 10.1021/acs.orglett.9b00695.
   PubMed Web of Science ®Google Scholar
• Dong, C.; Wu, L.; Yao, J.; Wei, K. Palladium-Catalyzed β-C–H Arylation of Aliphatic Aldehydes and Ketones Using Amino Amide as a Transient Directing Group. Org. Lett. 2019, 21, 2085–2089. DOI: 10.1021/acs.orglett.9b00366.
   PubMedGoogle Scholar
• Wu, Y. J.; Shi, B. F. Transition Metal-Catalyzed C − H Activation via Imine-Based Transient Directing Group Strategy. Chin. J. Org. Chem 2020. DOI: 10.6023/cjoc202003057.
   Web of Science ®Google Scholar
• Liao, G.; Wu, Y. J.; Shi, B. F. Noncovalent Interaction in Transition Metal-Catalyzed Selective C − H Activation. Acta Chim. Sinica 2020, 78, 289–298. DOI: 10.6023/A20020027.
   Web of Science ®Google Scholar
• Yao, Q. J.; Zhang, S.; Zhan, B. B.; Shi, B. F. Atroposelective Synthesis of Axially Chiral Biaryls by Palladium-Catalyzed Asymmetric C–H Olefination Enabled by a Transient Chiral Auxiliary. Angew. Chem. Int. Ed. Engl. 2017, 56, 6617–6621. DOI: 10.1002/anie.201701849.
   PubMed Web of Science ®Google Scholar
• Liao, G.; Yao, Q. J.; Zhang, Z. Z.; Wu, Y. J.; Huang, D. Y.; Shi, B. F. Scalable, Stereocontrolled Formal Syntheses of (+)-Isoschizandrin and (+)-Steganone: Development and Applications of Palladium(II)-Catalyzed Atroposelective C–H Alkynylation(+). Angew. Chem. Int. Ed. Engl. 2018, 57, 3661–3665. DOI: 10.1002/anie.201713106.
   PubMed Web of Science ®Google Scholar
• Liao, G.; Li, B.; Chen, H. M.; Yao, Q. J.; Xia, Y. N.; Luo, J.; Shi, B. F. Pd-Catalyzed Atroposelective C–H Allylation through β-O Elimination: Diverse Synthesis of Axially Chiral Biaryls. Angew. Chem. Int. Ed. Engl. 2018, 57, 17151–17155. DOI: 10.1002/anie.201811256.
   PubMed Web of Science ®Google Scholar
• Liao, G.; Chen, H. M.; Xia, Y. N.; Li, B.; Yao, Q. J.; Shi, B. F. Synthesis of Chiral Aldehyde Catalysts by Pd-Catalyzed Atroposelective C–H Naphthylation. Angew. Chem. Int. Ed. Engl. 2019, 58, 11464–11468. DOI: 10.1002/anie.201906700.
   PubMed Web of Science ®Google Scholar
• Zhang, S.; Yao, Q. J.; Liao, G.; Li, X.; Li, H.; Chen, H. M.; Hong, X.; Shi, B. F. Enantioselective Synthesis of Atropisomers Featuring Pentatomic Heteroaromatics by Pd-Catalyzed C–H Alkynylation. ACS Catal. 2019, 9, 1956–1961. DOI: 10.1021/acscatal.8b04870.
   Web of Science ®Google Scholar
• Chen, H. M.; Zhang, S.; Liao, G.; Yao, Q. J.; Xu, X. T.; Zhang, K.; Shi, B. F. Pd-Catalyzed Atroposelective C–H Allylation and Alkenylation: Access to Enantioenriched Atropisomers Featuring Pentatomic Heteroaromatics. Organometallics 2019, 38, 4022–4028. DOI: 10.1021/acs.organomet.9b00490.
   Web of Science ®Google Scholar
• Song, H.; Li, Y.; Yao, Q. J.; Jin, L.; Liu, L.; Liu, Y. H.; Shi, B. F. Synthesis of Axially Chiral Styrenes through Pd-Catalyzed Asymmetric C–H Olefination Enabled by an Amino Amide Transient Directing Group. Angew. Chem. Int. Ed. Engl. 2020, 59, 6576–6580. DOI: 10.1002/anie.201915949.
   PubMedGoogle Scholar
• Wu, Y. J.; Yao, Q. J.; Chen, H. M.; Liao, G.; Shi, B. F. Palladium-Catalyzed ortho-C–H Silylation of Biaryl Aldehydes Using a Transient Directing Group. Sci. China Chem. 2020, 63, 875–880. DOI: 10.1007/s11426-020-9694-3.
   Web of Science ®Google Scholar
• He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J. Q. Palladium-Catalyzed Transformations of Alkyl C–H Bonds. Chem. Rev. 2017, 117, 8754–8786. DOI: 10.1021/acs.chemrev.6b00622.
   PubMed Web of Science ®Google Scholar
• Sambiagio, C.; Schönbauer, D.; Blieck, R.; Dao-Huy, T.; Pototschnig, G.; Schaaf, P.; Wiesinger, T.; Zia, M. F.; Wencel-Delord, J.; Besset, T.; et al. A Comprehensive Overview of Directing Groups Applied in Metal-Catalysed C–H functionalisation chemistry. Chem. Soc. Rev. 2018, 47, 6603–6743. DOI: 10.1039/C8CS00201K.
   PubMed Web of Science ®Google Scholar
• Zhu, R. Y.; Farmer, M. E.; Chen, Y. Q.; Yu, J. Q. A Simple and Versatile Amide Directing Group for C–H Functionalizations. Angew. Chem. Int. Ed. Engl. 2016, 55, 10578–10599. DOI: 10.1002/anie.201600791.
   PubMed Web of Science ®Google Scholar
• Chu, J. C. K.; Rovis, T. Complementary Strategies for Directed C(sp3)-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer. Angew. Chem. Int. Ed. Engl. 2018, 57, 62–101. DOI: 10.1002/anie.201703743.
   PubMed Web of Science ®Google Scholar
• Lyons, T. W.; Sanford, M. S. Palladium-Catalyzed Ligand-Directed C–H functionalization reactions. Chem. Rev. 2010, 110, 1147–1169. DOI: 10.1021/cr900184e.
   PubMed Web of Science ®Google Scholar
• Li, B. J.; Shi, Z. J. From C(sp2)-H to C(sp3)-H: Systematic Studies on Transition Metal-Catalyzed Oxidative C–C Formation. Chem. Soc. Rev. 2012, 41, 5588–5598. DOI: 10.1039/C2CS35096C.
   PubMed Web of Science ®Google Scholar
• Li, H.; Li, B. J.; Shi, Z. J. Challenge and Progress: Palladium-Catalyzed sp3 C–H Activation. Catal. Sci. Technol. 2011, 1, 191–206. DOI: 10.1039/c0cy00076k.
   Web of Science ®Google Scholar
• He, G.; Wang, B.; Nack, W. A.; Chen, G. Syntheses and Transformations of α-Amino Acids via Palladium-Catalyzed Auxiliary-Directed sp3 C–H Functionalization. Acc. Chem. Res. 2016, 49, 635–645. DOI: 10.1021/acs.accounts.6b00022.
   PubMed Web of Science ®Google Scholar
• Zhang, Q.; Shi, B. F. From Reactivity and Regioselectivity to Stereoselectivity: An Odyssey of Designing PIP Amine and Related Directing Groups for C–H Activation. Chin. J. Chem. 2019, 37, 647–656. DOI: 10.1002/cjoc.201900090.
   Web of Science ®Google Scholar
• Chen, Z.; Rong, M. Y.; Nie, J.; Zhu, X. F.; Shi, B. F.; Ma, J. A. Catalytic Alkylation of Unactivated C(sp3)-H bonds for C(sp3)-C(sp3) bond formation. Chem. Soc. Rev. 2019, 48, 4921–4942. DOI: 10.1039/C9CS00086K.
   PubMed Web of Science ®Google Scholar
• John-Campbell, S. S.; Bull, J. A. Intramolecular Palladium(II)/(IV) Catalysed C(sp3)-H arylation of tertiary aldehydes using a transient imine directing group. Chem. Commun. (Camb.) 2019, 55, 9172–9175. DOI: 10.1039/C9CC03644J.
   PubMed Web of Science ®Google Scholar
• Yang, K.; Li, Q.; Liu, Y.; Li, G.; Ge, H. Catalytic C–H Arylation of Aliphatic Aldehydes Enabled by a Transient Ligand. J. Am. Chem. Soc. 2016, 138, 12775–12778. DOI: 10.1021/jacs.6b08478.
   PubMed Web of Science ®Google Scholar
• Hong, K.; Park, H.; Yu, J. Q. Methylene C(sp3)-H Arylation of Aliphatic Ketones Using a Transient Directing Group. ACS Catal. 2017, 7, 6938–6941. DOI: 10.1021/acscatal.7b02905.
   PubMed Web of Science ®Google Scholar
• John-Campbell, S. S.; Ou, A. K.; Bull, J. A. Palladium-Catalyzed C(sp3)-H Arylation of Primary Amines Using a Catalytic Alkyl Acetal to Form a Transient Directing Group. Chemistry 2018, 24, 17838–17843. DOI: 10.1002/chem.201804515.
   PubMed Web of Science ®Google Scholar
• Wu, Y.; Chen, Y. Q.; Liu, T.; Eastgate, M. D.; Yu, J. Q. Pd-Catalyzed γ-C(sp3)-H Arylation of Free Amines Using a Transient Directing Group. J. Am. Chem. Soc. 2016, 138, 14554–14557. DOI: 10.1021/jacs.6b09653.
   PubMed Web of Science ®Google Scholar
• Lin, H.; Wang, C.; Bannister, T. D.; Kamenecka, T. M. Site-Selective γ-C(sp3)-H and γ-C(sp2)-H Arylation of Free Amino Esters Promoted by a Catalytic Transient Directing Group. Chemistry 2018, 24, 9535–9541. DOI: 10.1002/chem.201802465.
   PubMed Web of Science ®Google Scholar
• Yu, X.; Lu, X. Efficient Synthesis of 9-Tosylaminofluorene Derivatives by Boron Trifluoride Etherate-Catalyzed Aza-Friedel–Crafts Reaction of in Situ Generated N-Tosylbenzaldimines. Adv. Synth. Catal. 2011, 353, 569–574. DOI: 10.1002/adsc.201000732.
   Web of Science ®Google Scholar
• Kuninobu, Y.; Tatsuzaki, T.; Matsuki, T.; Takai, K. Indium-Catalyzed Construction of Polycyclic Aromatic Hydrocarbon Skeletons via Dehydration. J. Org. Chem. 2011, 76, 7005–7009. DOI: 10.1021/jo200861s.
   PubMed Web of Science ®Google Scholar
• Hussain, A.; Parrick, J. Formation of 1-Chlorobenzocyclobutene, Anthracene or Benzofuran by Flash Vacuum Pyrolysis. Tetrahedron Lett 1983, 24, 609–612. DOI: 10.1016/S0040-4039(00)81477-X.
   Web of Science ®Google Scholar
• Rafiq, S. M.; Sivasakthikumaran, R.; Karunakaran, J.; Mohanakrishnan, A. K. Synthesis of Annulated Anthracenes, Carbazoles, and Thiophenes Involving Bradsher-Type Cyclodehydration or Cyclization–Reductive-Dehydration Reactions. Eur. J. Org. Chem. 2015, 2015, 5099–5114. DOI: 10.1002/ejoc.201500493.
   Web of Science ®Google Scholar
• Charlton, J. L.; Plourde, G. L.; Koh, K.; Secco, A. S. Asymmetric Synthesis of Podophyllotoxin Analogs. Can. J. Chem. 1990, 68, 2022–2027. DOI: 10.1139/v90-309.
   Web of Science ®Google Scholar
• Durst, T.; Kozma, E. C.; Charlton, J. L. Stereoselectivity in the Diels-Alder Reaction of Phenyl- and Oxy-Substituted o-Quinodimethanes. J. Org. Chem. 1985, 50, 4829–4833. DOI: 10.1021/jo00224a035.
   Web of Science ®Google Scholar
• Runyon, S. P.; Mosier, P. D.; Roth, B. L.; Glennon, R. A.; Westkaemper, R. B. Potential Modes of Interaction of 9-Aminomethyl-9,10-dihydroanthracene (AMDA) Derivatives with the 5-HT2A Receptor: A Ligand Structure-Affinity Relationship, Receptor Mutagenesis and Receptor Modeling Investigation. J. Med. Chem. 2008, 51, 6808–6828. DOI: 10.1021/jm800771x.
   PubMed Web of Science ®Google Scholar
• Patel, B. A.; Ashby, C. R.; Hardej, D.; Talele, T. T. The Synthesis and SAR Study of Phenylalanine-Derived (Z)-5-Arylmethylidene Rhodanines as anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Compounds. Bioorg. Med. Chem. Lett. 2013, 23, 5523–5527. DOI: 10.1016/j.bmcl.2013.08.059.
   PubMed Web of Science ®Google Scholar
• Wang, F.; Ueda, W. Aerobic Oxidation of Alcohols over Novel Crystalline Mo-V-O Oxide. Appl. Catal. A Gen 2008, 346, 155–163. DOI: 10.1016/j.apcata.2008.05.021.
   Web of Science ®Google Scholar
• Ganesamoorthy, S.; Shanmugasundaram, K.; Karvembu, R. Mild Oxidation of Alcohols with Periodic Acid Catalyzed by [Ru(acac)2(CH3CN)2]PF6 in Water. Catal. Commun 2009, 10, 1835–1838. DOI: 10.1016/j.catcom.2009.06.010.
   Web of Science ®Google Scholar
• Chan, G. H.; Ong, D. Y.; Yen, Z.; Chiba, S. Reduction of N,N-Dimethylcarboxamides to Aldehydes by Sodium Hydride–Iodide Composite. Helv. Chim. Acta 2018, 101, e1800049. DOI: 10.1002/hlca.201800049.
   Web of Science ®Google Scholar
• Bhattacharya, A. K.; Miller, B. Rearrangement and Fragmentation Reactions of Blocked Aromatic Alcohols. J. Am. Chem. Soc. 1983, 105, 3242–3247. DOI: 10.1021/ja00348a046.
   Web of Science ®Google Scholar
• Sun, A. D.; Leung, K.; Restivo, A. D.; Laberge, N. A.; Takasaki, H.; Love, J. A. Nickel-Catalyzed Csp2-Csp3 Bond Formation by carbon-fluorine activation. Chemistry 2014, 20, 3162–3168. DOI: 10.1002/chem.201303809.
   PubMed Web of Science ®Google Scholar
• Cong, X.; Tang, H.; Zeng, X. Regio- and Chemoselective Kumada-Tamao-Corriu Reaction of Aryl Alkyl Ethers Catalyzed by Chromium Under Mild Conditions. J. Am. Chem. Soc. 2015, 137, 14367–14372. DOI: 10.1021/jacs.5b08621.
   PubMed Web of Science ®Google Scholar
• Zhang, F. L.; Hong, K.; Li, T. J.; Park, H.; Yu, J. Q. Organic chemistry. Functionalization of C(sp3)-H bonds using a transient directing group. Science 2016, 351, 252–256. DOI: 10.1126/science.aad7893.
   PubMed Web of Science ®Google Scholar
• Tang, M.; Yu, Q.; Wang, Z.; Zhang, C.; Sun, B.; Yi, Y.; Zhang, F. L. Synthesis of Polycyclic Aromatic Hydrocarbons (PAHs) via a Transient Directing Group. Org. Lett. 2018, 20, 7620–7623. DOI: 10.1021/acs.orglett.8b03359.
   PubMed Web of Science ®Google Scholar
• Park, H.; Yoo, K.; Jung, B.; Kim, M. Direct Synthesis of Anthracenes from o-Tolualdehydes and Aryl Iodides through Pd(II)-Catalyzed sp3 C–H Arylation and Electrophilic Aromatic Cyclization. Tetrahedron 2018, 74, 2048–2055. DOI: 10.1016/j.tet.2018.03.006.
   Web of Science ®Google Scholar
• Wang, J. L.; Dong, C.; Wu, L. F.; Xu, M. K.; Lin, J.; Wei, K. Palladium-Catalyzed β-C − H Arylation of Ketones Using Amino Amide as a Transient Directing Group: Applications to Synthesis of Phenanthridinone Alkaloids. Adv. Synth. Catal. 2018, 360, 3709–3715. DOI: 10.1002/adsc.201800489.
   Google Scholar
• Ma, F.; Lei, M.; Hu, L. Acetohydrazone: A Transient Directing Group for Arylation of Unactivated C(sp3)-H Bonds. Org. Lett. 2016, 18, 2708–2711. DOI: 10.1021/acs.orglett.6b01170.
   PubMed Web of Science ®Google Scholar
• Wen, F.; Li, Z. Semicarbazide: A Transient Directing Group for C(sp3)−H Arylation of 2-Methylbenzaldehydes. Adv. Synth. Catal. 2020, 362, 133–138. DOI: 10.1002/adsc.201901392.
   Web of Science ®Google Scholar
• Wang, X.; Ding, J.; Vittal, J. Syntheses, Structures and Properties of Copper(II) Complexes Containing N-(2-Hydroxybenzyl)-Amino Amide Ligands. Inorg. Chim. Acta 2006, 359, 3481–3490. DOI: 10.1016/j.ica.2006.01.006.
   Google Scholar
• Yu, W.; Huang, G.; Zhang, Y.; Liu, H.; Dong, L.; Yu, X.; Li, Y.; Chang, J. I2-Mediated Oxidative C-O bond formation for the synthesis of 1,3,4-oxadiazoles from aldehydes and hydrazides. J. Org. Chem. 2013, 78, 10337–10343. DOI: 10.1021/jo401751h.
   PubMed Web of Science ®Google Scholar