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Organic Photoredox Catalyzed Direct Hydroamination of Ynamides with Azoles.

Authors :
Wang, Ban
Mccabe, Gavin E.
Parrish, Mitchell J.
Singh, Jujhar
Zeller, Matthias
Deng, Yongming
Source :
Advanced Synthesis & Catalysis. Mar2022, Vol. 364 Issue 6, p1179-1184. 6p.
Publication Year :
2022

Abstract

Disclosed herein is a photoinduced selective hydroamination of ynamides with nitrogen heteroaromatic nucleophiles. By using an organocatalytic photoredox system, a direct method to construct a diverse of (Z)‐α‐azole enamides from ynamides and pyrazoles, as well as triazoles, benzotriazoles, indazoles, and tetrazoles, is developed, thus providing a photocatalytically synthetic route to heterocyclic motifs common in medicinal agents. Based on the mechanistic studies, the hydroamination is postulated to operate via a mechanism in which the single‐electron oxidation of ynamide and the intermediacy of an alkyne radical cation, is responsible for the observed reactivity. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
16154150
Volume :
364
Issue :
6
Database :
Academic Search Index
Journal :
Advanced Synthesis & Catalysis
Publication Type :
Academic Journal
Accession number :
155809160
Full Text :
https://doi.org/10.1002/adsc.202101410