Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts

Scholarly Works

• Li, Q.; Han, Y.; Pu, J.; Jia, X.; Han, L.; Hou, J.; Wei, L.; Ma, W. Research Progress on the Formation of C-C Bonds through Photoinduced Cross-coupling Reactions Involving Katritzky Salts. Mini-Reviews in Organic Chemistry 2025, 22, 621–637. doi:10.2174/0118756298307537240722112735
• Templ, J.; Schnürch, M. Strategies for Using Quaternary Ammonium Salts as Alternative Reagents in Alkylations. Chemistry (Weinheim an der Bergstrasse, Germany) 2024, 30, e202400675. doi:10.1002/chem.202400675
• 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
• Filipović, A.; Džambaski, Z.; Bondžić, A. M.; Bondžić, B. P. Visible-light promoted photoredox catalysis in flow: addition of biologically important α‑amino radicals to michael acceptors. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 2023, 22, 2259–2270. doi:10.1007/s43630-023-00448-8
• Wang, P.; Meng, K.; Guo, S.; Wang, M.; Gao, Y.; Wang, Y. Photoinduced α‐Alkylation of Tetrahydroisoquinolines with Organoboron Reagent Enabled by Organic Photocatalyst. European Journal of Organic Chemistry 2023, 26. doi:10.1002/ejoc.202201157
• Pu, J.; Jia, X.; Han, L.; Li, Q. Research Progress of Visible Light Promoted C—N Bond Fracture to Construct C—C Bond. Chinese Journal of Organic Chemistry 2023, 43, 2591. doi:10.6023/cjoc202302002
• Elavarasan, S.; Preety, J.; Abinaya, R.; Saravanan, T.; Balasubramanian, K. K.; Venkatramaiah, N.; Baskar, B. Visible Light Driven Metal-Free Photoredox Catalyzed α-benzylation and α-oxygenation of N-substituted Tetrahydroisoquinolines: Applications to Synthesis of Natural Products. Chemistry, an Asian journal 2022, 17, e202200878. doi:10.1002/asia.202200878
• Gao, Y.; Jiang, S.; Mao, N.-D.; Xiang, H.; Duan, J.-L.; Ye, X.-Y.; Wang, L.-W.; Ye, Y.; Xie, T. Recent Progress in Fragmentation of Katritzky Salts Enabling Formation of C-C, C-B, and C-S Bonds. Topics in current chemistry (Cham) 2022, 380, 25. doi:10.1007/s41061-022-00381-x
• Dorsheimer, J. R.; Ashley, M. A.; Rovis, T. Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines. Journal of the American Chemical Society 2021, 143, 19294–19299. doi:10.1021/jacs.1c10150
• Guo, X.; Shao, B.-r.; Jiang, W.-f.; Shi, L. The Photocatalyst-Free Cross-Dehydrogenative Coupling Reaction Enabled by Visible-Light Direct Excitation of Substrate. The Journal of organic chemistry 2021, 86, 15743–15752. doi:10.1021/acs.joc.1c01775
• Boldt, A. M.; Dickinson, S. I.; Ramirez, J. R.; Benz-Weeden, A. M.; Wilson, D. S.; Stevenson, S. M. Reactions of benzyltriphenylphosphonium salts under photoredox catalysis. Organic & biomolecular chemistry 2021, 19, 7810–7815. doi:10.1039/d1ob01570b
• Ma, P.; Liu, Y.; Chen, L.; Zhao, X.; Yang, B.; Zhang, J. Photocatalyst- and additive-free decarboxylative alkylation of N-aryl tetrahydroisoquinolines induced by visible light. Organic Chemistry Frontiers 2021, 8, 2473–2479. doi:10.1039/d1qo00261a
• Filipović, A.; Džambaski, Z.; Vasiljević-Radović, D.; Bondžić, B. P. Visible light promoted photoredox C(sp3)-H bond functionalization of tetrahydroisoquinolines in flow. Organic & biomolecular chemistry 2021, 19, 2668–2675. doi:10.1039/d0ob02582h
• Sambiagio, C.; Ferrari, M.; van Beurden, K.; Della Ca, N.; van Schijndel, J.; Noël, T. Continuous-Flow Synthesis of Pyrylium Tetrafluoroborates: Application to Synthesis of Katritzky Salts and Photoinduced Cationic RAFT Polymerization. Organic letters 2021, 23, 2042–2047. doi:10.1021/acs.orglett.1c00178
• Berger, K. J.; Levin, M. D. Reframing primary alkyl amines as aliphatic building blocks. Organic & biomolecular chemistry 2021, 19, 11–36. doi:10.1039/d0ob01807d
• Rickertsen, D. R. L.; Ma, L.; Paul, A.; Abboud, K. A.; Seidel, D. Traceless Redox-Annulations of Alicyclic Amines. SynOpen (2017) 2020, 04, 123–131. doi:10.1055/s-0040-1706004
• Ashley, M. A.; Rovis, T. Photoredox-Catalyzed Deaminative Alkylation via C-N Bond Activation of Primary Amines. Journal of the American Chemical Society 2020, 142, 18310–18316. doi:10.1021/jacs.0c08595

Explore citations to this article at