Acid-promoted selective synthesis of trifluoromethylselenolated benzofurans with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate

A Bronsted acid-promoted trifluoromethylselenolation of benzofurans was disclosed by using Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate as a stable and easily prepared electrophilic trifluoromethylselenolating reagent. A wide range of SeCF3-substituted benzofuran derivatives were obtained in moderate to good yields with excellent regioselectivity. The tandem cyclization/trifluoromethylselenolation procedure of 1-methoxy-2-(arylethynyl)benzenes were also realized by engaging FeCl3 as the catalyst. (C) 2021 Elsevier Ltd. All rights reserved.

Automated summary

A Bronsted acid-promoted trifluoromethylselenolation of benzofurans using a stable and easily prepared electrophilic trifluoromethylselenolating reagent was disclosed, resulting in a range of SeCF3-substituted benzofuran derivatives with moderate to good yields and excellent regioselectivity. Additionally, a tandem cyclization/trifluoromethylselenolation procedure of specific compounds was achieved by employing FeCl3 as the catalyst.