Aryl Methyl Sulfides as Substrates for Rhodium-Catalyzed Alkyne Carbothiolation: Arene Functionalization with Activating Group Recycling

• DOI: 10.1021/ja2108992
• Publication Date: 2012-01-30T20:20:41Z
• Authors: Joel F. Hooper; Adrian B. Chaplin; Carlos González-R...; Amber L. Thompson; Andrew S. Weller; Michael C. Willis
• Keywords: Alkyne; Alkene; Surface Modification; Hydroacylation; Functional group

A Rh(I)-catalyzed method for the efficient functionalization of arenes is reported. Aryl methyl sulfides are combined with terminal alkynes to deliver products carbothiolation. The overall process results in reincorporation original arene functional group, a sulfide, into as an alkenyl sulfide. carbothiolation can be initial alkene or alkyne hydroacylation reaction three-component cascade sequences. utility sulfide also demonstrated simple carbo- and heterocycle-forming processes. We provide mechanistic evidence course this new process.