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Updated: Sep 5, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Nickel-catalyzed Thioester Transfer Reaction with sp2-Hybridized Electrophiles
Xiaopeng Wu1, Jinhang Li1, Siyu Xia1
1State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
Abstract:
We report a thioacylation transfer reaction based on nickel-catalyzed C-C bond cleavage of thioesters with sp2-hybridized electrophiles. Aryl bromides, iodides, and alkenyl triflates can participate in thioester transfer reaction of aryl thioesters, affording a wide range of structurally diverse new thioesters in yields of up to 98% under mild reaction conditions. With this protocol, it is possible to construct alkenyl thioesters from the corresponding ketones through the generation of alkenyl triflates.
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