Organophotocatalytic ring opening/remote trifluoromethylselenolation of cycloalkanols

An organophotocatalytic ring opening/remote trifluoromethylselenolation of cycloalkanols is reported. This reaction proceeds the radical ring-opening in a photocatalytic system without metal catalysis under mild conditions, followed by the formation of the remote C(sp3)-SeCF3 bond in the presence of PhSO2SeCF3. The reaction brings out highly reactive to prepare trifluoromethylselenolated carbonyl compounds, suitable for a variety of aryl cyclic alcohols, while compatible with different ring systems with high yield, including 26 examples, the highest isolated yield of 93%. (c) 2022 Elsevier Ltd. All rights reserved.

Automated summary

An organophotocatalytic ring opening/remote trifluoromethylselenolation reaction of cycloalkanols is reported. This reaction proceeds via radical ring-opening in a photocatalytic system without metal catalysis under mild conditions, followed by the formation of remote C(sp3)-SeCF3 bond. The reaction shows high yield and compatibility with various aryl cyclic alcohols and different ring systems.