Issue 4, 2023

Visible light-mediated NHC and photoredox co-catalyzed 1,2-sulfonylacylation of allenes via acyl and allyl radical cross-coupling

Abstract

Allyl radicals serve as a crucial intermediate in the radical functionalization of fundamental raw materials and have received increasing attention. Despite their significance, radical cross-couplings involving allyl radicals are rare and mainly focus on couplings with aryl or benzyl radical analogs. Herein, we realized radical 1,2-sulfonylacylation of allenes via an unprecedented cross-coupling between an NHC-stabilized acyl radical and a delocalized allyl radical. Cheap and stable sulfinates and readily accessible acyl sources could be installed into allene units with excellent regioselectivity by the cooperation of visible light catalysis and NHC catalysis. This versatile protocol provides an attractive strategy for valuable sulfonyl-containing multi-substituted allyl ketones under extremely mild conditions with broad functional group tolerance, which might open a new avenue for the radical difunctionalization of allenes.

Graphical abstract: Visible light-mediated NHC and photoredox co-catalyzed 1,2-sulfonylacylation of allenes via acyl and allyl radical cross-coupling

Supplementary files

Article information

Article type
Research Article
Submitted
16 12 2022
Accepted
31 12 2022
First published
03 1 2023

Org. Chem. Front., 2023,10, 1047-1055

Visible light-mediated NHC and photoredox co-catalyzed 1,2-sulfonylacylation of allenes via acyl and allyl radical cross-coupling

L. Wang, J. Sun, J. Xia, R. Ma, G. Zheng and Q. Zhang, Org. Chem. Front., 2023, 10, 1047 DOI: 10.1039/D2QO01993K

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