Issue 19, 2022

Redox-neutral ketyl radical coupling/cyclization of carbonyls with N-aryl acrylamides through consecutive photoinduced electron transfer

Abstract

While the reductive ketyl couplings of carbonyls have been widely explored, we report in this work on a redox-neutral umpolung carbonyl coupling reaction through ketyl radical formation by consecutive photoinduced electron transfer (ConPET) under metal- and additive-free conditions. The donor–acceptor cyanoarene-based fluorophore, 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN), was used as an efficient photocatalyst. It undergoes ConPET to form the excited radical anion (4CzIPN˙*) possessing high reductive potential without an external electron donor. This mild and simple photocatalytic system allows highly efficient coupling/cyclization of N-aryl acrylamides and carbonyls and provides straightforward access to structurally useful hydroxyalkyl oxindoles with formal 100% atom economy.

Graphical abstract: Redox-neutral ketyl radical coupling/cyclization of carbonyls with N-aryl acrylamides through consecutive photoinduced electron transfer

Supplementary files

Article information

Article type
Paper
Submitted
24 may 2022
Accepted
12 iyl 2022
First published
13 iyl 2022

Green Chem., 2022,24, 7403-7409

Redox-neutral ketyl radical coupling/cyclization of carbonyls with N-aryl acrylamides through consecutive photoinduced electron transfer

Z. Qu, T. Tian, Y. Tan, X. Ji, G. Deng and H. Huang, Green Chem., 2022, 24, 7403 DOI: 10.1039/D2GC01966C

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