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Oxidative Amidation of Amines in Tandem with Transamidation: A Route to Amides Using Visible-Light Energy.

Authors :
Nandi J
Vaughan MZ
Sandoval AL
Paolillo JM
Leadbeater NE
Source :
The Journal of organic chemistry [J Org Chem] 2020 Jul 17; Vol. 85 (14), pp. 9219-9229. Date of Electronic Publication: 2020 Jun 26.
Publication Year :
2020

Abstract

A methodology is reported for preparing amides using amines as an acyl source. The protocol involves the visible-light-promoted oxidative amidation of amines with pyrazole to synthesize N -acyl pyrazoles followed by transamidation. By combining photoredox catalysis with oxoammonium cations in the presence of sodium persulfate as a terminal oxidant, the N -acyl pyrazoles could be prepared efficiently and effectively using blue LEDs. The transamidation step was performed without the need to purify the N -acyl pyrazole intermediate, and a range of amides were generated in good to excellent yields.

Details

Language :
English
ISSN :
1520-6904
Volume :
85
Issue :
14
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
32539393
Full Text :
https://doi.org/10.1021/acs.joc.0c01222