Copper-catalyzed asymmetric sp³ C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

Scholarly Works

• Borah, B.; Chowhan, L. R. Photocatalytic asymmetric cross-dehydrogenative coupling of tetrahydroisoquinoline scaffolds. Tetrahedron Letters 2025, 164, 155630. doi:10.1016/j.tetlet.2025.155630
• Chhavi; Jha, R. K.; Parganiha, D.; Sharangi, S.; Kumar, S. Blue-Light-Irradiated Copper-Catalyzed Regio-tunable Double C-H/C-H Cross-Coupling Reaction: A Sustainable Approach to Construct C2-Indolyl-1,4-naphthoquinones. The Journal of organic chemistry 2025, 90, 8917–8935. doi:10.1021/acs.joc.5c00513
• Liu, Y.; Li, X.; Li, J. Photocatalytic and electrocatalytic α-C–H functionalization of tertiary amines. Tetrahedron 2024, 166, 134234. doi:10.1016/j.tet.2024.134234
• Newar, U. D.; Boruah, D. J.; Bhuyan, A.; Nayak, A.; Maurya, R. A. Visible-light-induced copper-catalyzed oxidative esterification of α-azidoketones with diazoacetates: access to α-acyloxyacetates. Organic & biomolecular chemistry 2024, 22, 5414–5418. doi:10.1039/d4ob00590b
• Jia, Y.; He, X.-K.; Lu, L.-Q.; Xiao, W.-J. Asymmetric Oxidation Using Photocatalysis. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering; Elsevier, 2024. doi:10.1016/b978-0-323-96025-0.00113-7
• Faure, C.; Yuan, Y.; Belmont, P.; Brachet, E. Asymmetric Dual Catalytic Processes: Transition Metal Catalysis and Photoredox Catalysis. Comprehensive Chirality; Elsevier, 2024; pp 236–250. doi:10.1016/b978-0-32-390644-9.00143-8
• Cong, F.; Zhang, W.; Zhang, G.; Liu, J.; Zhang, Y.; Zhou, C.; Wang, L. Visible light as a sole requirement for alkylation of α-C(sp3)-H of N-aryltetrahydroisoquinolines with alkylboronic acids. Organic & biomolecular chemistry 2023, 21, 8910–8917. doi:10.1039/d3ob01154b
• Sana, S.; Dastari, S.; Reddy, D. S.; Tokala, R.; Sathish, M.; Sonti, R.; Shankaraiah, N. Visible-light-mediated photocatalytic sequential N-arylation: an eco-friendly synthetic route to unsymmetrical diarylamines and the imatinib drug. Organic Chemistry Frontiers 2023, 10, 4573–4580. doi:10.1039/d3qo00894k
• Liang, K.; Zhang, D.; Su, Y.; Lu, L.; Hu, J.; Chen, Y.-H.; Zhang, X.; Lei, A.; Yi, H. Fragile intermediate identification and reactivity elucidation in electrochemical oxidative α-C(sp3)-H functionalization of tertiary amines. Chemical science 2023, 14, 4152–4157. doi:10.1039/d3sc00527e
• Song, L.; Cai, L.; Gong, L.; Van der Eycken, E. V. Photoinduced copper-catalyzed enantioselective coupling reactions. Chemical Society reviews 2023, 52, 2358–2376. doi:10.1039/d2cs00734g
• Akita, M. doi:10.1002/9783527834242.chf0210
• Kumar, V.; Mantry, L.; Maayuri, R.; Gandeepan, P. doi:10.1002/9783527834242.chf0052
• Xu, J.-H.; Liu, Z.-K.; Tang, Y.-L.; Gao, Y.; Hu, X.-Q. Merging strain-release and copper catalysis: the selective ring-opening cross-coupling of 1,2-oxazetidines with boronic acids. Chemical communications (Cambridge, England) 2022, 58, 4180–4183. doi:10.1039/d2cc00461e
• Wei, B.; Qin, J.-H.; Yang, Y.-Z.; Xie, Y.-X.; Ouyang, X.-H.; Song, R.-J. Electrochemical radical C(sp3)–H arylation of xanthenes with electron-rich arenes. Organic Chemistry Frontiers 2022, 9, 816–821. doi:10.1039/d1qo01714d
• Song, L.; Fu, N. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering - Single-Electron Strategies in Organometallic Methods: Photoredox, Electrocatalysis, Radical Relay, and Beyond. Comprehensive Organometallic Chemistry IV; Elsevier, 2022; pp 339–403. doi:10.1016/b978-0-12-820206-7.00094-9
• Lu, F.-D.; Chen, J.; Jiang, X.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Recent advances in transition-metal-catalysed asymmetric coupling reactions with light intervention. Chemical Society reviews 2021, 50, 12808–12827. doi:10.1039/d1cs00210d
• Holmberg-Douglas, N.; Nicewicz, D. A. Photoredox-Catalyzed C-H Functionalization Reactions. Chemical reviews 2021, 122, 1925–2016. doi:10.1021/acs.chemrev.1c00311
• Tashrifi, Z.; Khanaposhtani, M. M.; Larijani, B.; Mahdavi, M. C1-Functionalization of 1,2,3,4-Tetrahydroisoquinolines (THIQs). Asian Journal of Organic Chemistry 2021, 10, 2421–2439. doi:10.1002/ajoc.202100407
• Deng, Z.; Feng, J.; Zhou, F.; Ouyang, Y.; Ma, H.; Zhou, W.; Zhang, X.; Cai, Q. Copper(I)–catalyzed intramolecular asymmetric C-arylation of acyclic β-ester amides: enantioselective formation of chiral oxindoles. Organic Chemistry Frontiers 2021, 8, 4211–4216. doi:10.1039/d1qo00568e
• Li, Y.; Ye, Z.; Cai, J.; Gong, L. Visible-Light-Promoted Asymmetric Catalysis by Chiral Complexes of First-Row Transition Metals. Synthesis 2020, 53, 1570–1583. doi:10.1055/a-1344-2473

Explore citations to this article at