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

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–accept...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2022-10, Vol.24 (19), p.7403-7409
Main Authors: Qu, Zhonghua, Tian, Tong, Tan, Yongbo, Ji, Xiaochen, Deng, Guo-Jun, Huang, Huawen
Format: Article
Language:English
Subjects:
Aromatic compounds
Atom economy
Carbonyl compounds
Carbonyls
Couplings
Electron transfer
Green chemistry
Photocatalysis
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Summary: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.
ISSN:1463-9262
1463-9270
DOI:10.1039/D2GC01966C