Ketone Synthesis via Irradiation-Induced Generation of a Persistent Ketyl Radical from Acyl Azolium Salts

A novel three-component α-acylated difunctionalization of alkenes strategy has been developed on the basis of a direct hydrogen atom transfer (HAT) process of photoinduced acyl azolium salts. With simple irradiation without the catalyst, a variety of olefins can be directly converted into ketone der...

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Bibliographic Details
Published in:Organic letters 2023-09, Vol.25 (35), p.6522-6527
Main Authors: Li, Shihao, Zheng, Chenglong, Wang, Sheng, Li, Xiao-Xuan, Zhang, Qi, Fan, Shilu, Feng, Yi-Si
Format: Article
Language:English
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Summary:A novel three-component α-acylated difunctionalization of alkenes strategy has been developed on the basis of a direct hydrogen atom transfer (HAT) process of photoinduced acyl azolium salts. With simple irradiation without the catalyst, a variety of olefins can be directly converted into ketone derivatives, including 1,4-dione, β-silyl ketone, 1,5-dione, etc. Mechanistic investigations indicated that the unique reactivity of the acyl azonium triplet excited state is crucial to the strategy’s success.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c02300