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Updated: Aug 9, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Deacylative Thiolation by Redox-Neutral Aromatization-Driven C-C Fragmentation of Ketones
Xukai Zhou1, Daniel Pyle1, Zining Zhang1
1Department of Chemistry, The University of Chicago, 5735 S Ellis Ave, Chicago, IL, 60637, USA.
Abstract:
Herein we report the development of deacylative thiolation of diverse methyl ketones. The reaction is redox-neutral, and heavy-metal-free, which provides a new way to introduce thioether groups site-specifically to unactivated aliphatic positions. It also features excellent functional group tolerance and broad substrate scope, thus allowing late-stage derivatization. The process benefits from efficient condensation between the activation reagent and ketone substrates, which triggers aromatization-driven C-C fragmentation and rapid radical coupling with thiosulfonates. Experimental and computational mechanistic studies suggest the involvement of a radical chain pathway.
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