Issue 3, 2020

Photocatalyst- and transition-metal-free α-allylation of N-aryl tetrahydroisoquinolines mediated by visible light

Abstract

A convenient and efficient α-allylation of N-aryl tetrahydroisoquinolines has been achieved. This transformation can be realized under only visible light irradiation without the aid of transition metals or photocatalysts. The mechanism involves a novel in situ-generated electron-donor–acceptor (EDA) complex between the N-aryl tetrahydroisoquinolines and an allyl or a benzyl bromide. Irradiation with purple light triggered single-electron transfer (SET) from the N-aryl tetrahydroisoquinolines to the allyl or benzyl bromide of the EDA complex, inducing the formation of the corresponding allyl or benzyl radical and the subsequent radical–radical coupling. This approach represents the first example of a photocatalyst- and transition-metal-free α-allylic and benzylic functionalization of N-aryl tetrahydroisoquinolines.

Graphical abstract: Photocatalyst- and transition-metal-free α-allylation of N-aryl tetrahydroisoquinolines mediated by visible light

Supplementary files

Article information

Article type
Communication
Submitted
17 آذر 1398
Accepted
23 دی 1398
First published
23 دی 1398

Green Chem., 2020,22, 646-650

Photocatalyst- and transition-metal-free α-allylation of N-aryl tetrahydroisoquinolines mediated by visible light

Z. Li, P. Ma, Y. Tan, Y. Liu, M. Gao, Y. Zhang, B. Yang, X. Huang, Y. Gao and J. Zhang, Green Chem., 2020, 22, 646 DOI: 10.1039/C9GC04191E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements