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Photoredox Catalytic Trifluoromethylation and Perfluoroalkylation of (Hetero)Arenes Using Trifluoroacetic and Related Carboxylic Acids

181 Pages Posted: 10 Jun 2020 Sneak Peek Status: Review Complete

See all articles by Dehang Yin

Dehang Yin

Chinese Academy of Sciences (CAS) - Shanghai Institute of Organic Chemistry

Dengquan Su

Chinese Academy of Sciences (CAS) - Shanghai Institute of Organic Chemistry

Jian Jin

Chinese Academy of Sciences (CAS) - CAS Key Laboratory of Synthetic Chemistry of Natural Substances

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Abstract

A mild and practical method has been achieved that allows for the direct C–H trifluoromethylation, perfuoroalkylation and chlorodifluoromethylation of (hetero)arenes using inexpensive, abundant trifluoroacetic acid and the related carboxylic acids. A diverse array of arenes and heteroarenes were successfully transformed into valued fluoroalkylated compounds. The combination of photoredox catalysis and a diaryl sulfoxide provides a platform for the facile generation of fluoroalkyl radicals from the corresponding fluoroalkyl carboxylic acids under mild conditions.

Keywords: photoredox catalysis, trifluoromethylation, perfluoroalkylation, trifluoroacetic acid, arenes

Suggested Citation

Yin, Dehang and Su, Dengquan and Jin, Jian, Photoredox Catalytic Trifluoromethylation and Perfluoroalkylation of (Hetero)Arenes Using Trifluoroacetic and Related Carboxylic Acids. Available at SSRN: https://ssrn.com/abstract=3606764 or http://dx.doi.org/10.2139/ssrn.3606764
This is a paper under consideration at Cell Press and has not been peer-reviewed.

Dehang Yin

Chinese Academy of Sciences (CAS) - Shanghai Institute of Organic Chemistry

Building 7, NO. 80 Zhongguancun Road
Beijing, 100190
China

Dengquan Su

Chinese Academy of Sciences (CAS) - Shanghai Institute of Organic Chemistry

Building 7, NO. 80 Zhongguancun Road
Beijing, 100190
China

Jian Jin (Contact Author)

Chinese Academy of Sciences (CAS) - CAS Key Laboratory of Synthetic Chemistry of Natural Substances

Building 7, NO. 80 Zhongguancun Road
Beijing, Beijing 100190
China

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