Weiyu Yin’s work has been published in Adv.Synth.Catal.

Highly ortho-Selective Trifluoromethylthiolation Reactions using a Ligand Exchange Strategy

Weiyu Yin, ZhaofengWang and Yong Huang*, Adv. Synth. Catal. 2014, 356, 2998 – 3006

The trifluoromethylthio group (SCF₃) is a highly privileged modifier for drug molecules. Direct CH trifluoromethylthiolation reactions are highly valuable synthetic tools for the late-stage modification of drug candidates, which have so far been underexplored. We report a palladium-catalyzed ortho-selective mono-trifluoromethylthiolation reaction of arenes. The reaction proceeds through a key ligand exchange pathway using readily available silver trifluoromethylthiolate (AgSCF₃). Acetic acid was found to be crucial to minimize oxidative dimerization of the starting materials and to facilitate the “SCF₃⁻” transfer. We expect this strategy to have broad applications in CH functionalization reactions using a stand-alone oxidant and various anions.