Issue 44, 2023

Visible light as a sole requirement for alkylation of α-C(sp3)–H of N-aryltetrahydroisoquinolines with alkylboronic acids

Abstract

An alkylation of α-C(sp3)–H at N-aryltetrahydroisoquinolines with alkylboronic acids was developed under visible-light irradiation in the absence of additional photocatalyst. The reaction proceeded well, tolerating a variety of functional groups, and featured low-cost and mild reaction conditions. A preliminary mechanistic study indicated that an electron donor–acceptor (EDA) complex between an electron-rich N-aryltetrahydroisoquinoline and an electron-poor alkylboronic acid was involved in the reaction.

Graphical abstract: Visible light as a sole requirement for alkylation of α-C(sp3)–H of N-aryltetrahydroisoquinolines with alkylboronic acids

Supplementary files

Article information

Article type
Paper
Submitted
21 Jul 2023
Accepted
05 Oct 2023
First published
15 Oct 2023

Org. Biomol. Chem., 2023,21, 8910-8917

Visible light as a sole requirement for alkylation of α-C(sp3)–H of N-aryltetrahydroisoquinolines with alkylboronic acids

F. Cong, W. Zhang, G. Zhang, J. Liu, Y. Zhang, C. Zhou and L. Wang, Org. Biomol. Chem., 2023, 21, 8910 DOI: 10.1039/D3OB01154B

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