Copper-Catalyzed Oxidative Trifluoromethylation of Aromatic Alkenes for the Synthesis of α-Trifluoromethylated Ketones

作者：Wang, Jiali; Liu, Hongjian; Qi, Chaorong^*

来源：Asian Journal of Organic Chemistry, 2024.

DOI：10.1002/ajoc.202300638

• alkenes
• copper catalysis
• ketones
• oxidation
• trifluoromethylation

A copper-catalyzed oxidative trifluoromethylation of aromatic alkenes has been developed successfully, providing access to a variety of valuable alpha-trifluoromethyl-substituted ketones using Togni's reagent as the trifluoromethyl source. The use of affordable copper catalyst and readily available alkenes as the feedstock, broad substrate scope, mild conditions, and operational simplicity are the attractive features of the method. Preliminary mechanistic studies revealed that both dimethyl sulfoxide (DMSO) and air might function as the oxidant for the transformation. @@@ A new method for the synthesis of a wide range of synthetically valuable alpha-trifluoromethylated ketones has been established via a copper-catalyzed oxidative trifluoromethylation of aromatic alkenes. The use of affordable copper catalyst and readily available alkenes as the feedstocks, mild conditions and broad substrate scope are the attractive features of the protocol. image