Direct a-Trifluoromethylthiolation of Carboxylic Acids Enabled by Boron Catalysis

Kai Sun,Chung-Yang Dennis Huang,Masaya Sawamura,Yohei Shimizu

SYNLETT（2023）

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摘要

A boron-catalyzed direct a-trifluoromethylthiolation of carboxylic acids was developed. Catalytically generated boron enediolates reacts with electrophilic SCF3 reagent, N-SCF3-phthalimide, to provide a-SCF3 carboxylic acids without the need of substrate pre-activation. The method is applicable to direct modification of bioactive carboxylic acids. Data science analyses provided suitable models for substrate clas-sification as well as yield prediction.

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关键词

carboxylic acid, boron catalyst, trifluoromethylthiolation, data science, drug modification, fluorine compounds

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