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Decatungstate Catalyzed Synthesis of Trifluoromethylthioesters from Aldehydes via a Radical Process
Journal article   Peer reviewed

Decatungstate Catalyzed Synthesis of Trifluoromethylthioesters from Aldehydes via a Radical Process

Zhegao Ye, Ziran Lei, Xiaodong Ye, Liejin Zhou, Yanan Wang, Zheliang Yuan, Feng Gao and Robert Britton
Journal of organic chemistry, Vol.87(1), pp.765-775
07/01/2022
PMID: 34882428

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
Here we report a mild and general method for the trifluoromethylthiolation of aldehydes using N-trifluorometh-ylthiosaccharin as the CF3S radical source and sodium decatungstate (NaDT) as the photocatalyst. This reaction proceeds via hydrogen atom abstraction by photoactivated DT and features good functional groups and substrate tolerance. Generally, electronrich aldehydes demonstrate better reactivity than electron-deficient ones and good selectivity is observed for the trifluoromethylthiolation of aldehydic C-H bonds over tertiary and benzylic C-H bonds. Preliminary mechanistic studies have shown that a free radical process is involved.

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