Organoelectrophotocatalytic Generation of Acyl Radicals from Formamides and Aldehydes: Access to Acylated 3‑CF3‑2-Oxindoles

Organoelectrophotocatalytic generation of acyl radicals from formamides and aldehydes to synthesize acylated 3-CF3-2-oxindoles has been developed. This protocol features a monocatalytic system using 9,10-phenanthrenequinone (PQ) both as a catalyst and as a hydrogen atom transfer (HAT) reagent, which...

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Bibliographic Details
Published in:Organic letters 2023-09, Vol.25 (38), p.7014-7019
Main Authors: He, Hong, Wan, Qinhui, Hou, Zhong-Wei, Zhou, Quan, Wang, Lei
Format: Article
Language:English
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Summary:Organoelectrophotocatalytic generation of acyl radicals from formamides and aldehydes to synthesize acylated 3-CF3-2-oxindoles has been developed. This protocol features a monocatalytic system using 9,10-phenanthrenequinone (PQ) both as a catalyst and as a hydrogen atom transfer (HAT) reagent, which avoids the use of an external HAT reagent, metal reagent, and oxidant. A variety of acylated 3-CF3-2-oxindoles have been obtained in satisfactory yields from CF3-substituted N-arylacrylamides via a tandem radical cyclization.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c02607