Issue 43, 2022

Visible-light-induced dual catalysis for N-α C(sp3)–H amination and alkenylation of N-alkyl benzamides

Abstract

The amination and alkenylation of the C(sp3)–H bond at the N-α position of secondary benzamides were both realized in this work by using N-hydroxyphthalimide (NHPI) imidate esters as substrates under a dual catalysis involving a photoredox catalyst and hydrogen atom transfer (HAT) catalyst. The developed methods significantly extended the scope of applications of the N-α position C(sp3)–H bond functionalization with regard to secondary N-alkylamides. More importantly, new reaction models in photoredox catalysis have been established. Based on corresponding experiments and density functional theory (DFT) calculations on the critical reaction steps combined with information reported previously, we proposed a synergistic photo- and organocatalytic reaction process for the C(sp3)–H bond functionalization and also clarified the occurrence of a chain process in the reaction pathway.

Graphical abstract: Visible-light-induced dual catalysis for N-α C(sp3)–H amination and alkenylation of N-alkyl benzamides

Supplementary files

Article information

Article type
Edge Article
Submitted
17 Jun 2022
Accepted
30 Sep 2022
First published
12 Oct 2022
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., 2022,13, 12851-12857

Visible-light-induced dual catalysis for N-α C(sp3)–H amination and alkenylation of N-alkyl benzamides

L. Li, X. Gu, M. Shi and Y. Wei, Chem. Sci., 2022, 13, 12851 DOI: 10.1039/D2SC03385B

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