Issue 16, 2020

Diastereoselective olefin amidoacylation via photoredox PCET/nickel-dual catalysis: reaction scope and mechanistic insights

Abstract

The selective 1,2-aminoacylation of olefins provides opportunities for the rapid construction of nitrogen-containing molecules. However, the lack of CO-free acylation reactions has limited their application. By using photoredox proton-coupled electron transfer (PCET)/Ni dual-catalysis, a highly regio- and diastereoselective amidoacylation of unactivated olefins has been developed. Various acyl electrophiles are compatible, including alkyl- and aryl acyl chlorides and anhydrides, as well as in situ activated carboxylic acids. Hammett studies and other mechanistic experiments to elucidate features of the diastereoselectivity, a transient absorption study of the PCET step, as well as computational evidence, provide an in-depth understanding of the disclosed transformation.

Graphical abstract: Diastereoselective olefin amidoacylation via photoredox PCET/nickel-dual catalysis: reaction scope and mechanistic insights

Supplementary files

Article information

Article type
Edge Article
Submitted
10 Mär 2020
Accepted
01 Apr 2020
First published
01 Apr 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 4131-4137

Diastereoselective olefin amidoacylation via photoredox PCET/nickel-dual catalysis: reaction scope and mechanistic insights

S. Zheng, S. Zhang, B. Saeednia, J. Zhou, J. M. Anna, X. Hong and G. A. Molander, Chem. Sci., 2020, 11, 4131 DOI: 10.1039/D0SC01459A

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