Gold(I)-catalyzed reactions of thiols, thiophenols, and thioacids with 3,3-disubstituted cyclopropenes occur in a regioselective and chemoselective manner to produce either vinyl thioethers or primary allylic thioesters in good yields. A survey of commonly used gold(I) catalysts shows Echavarren’s cationic gold(I) catalyst to be most tolerant of deactivation by sulfur. A novel digold with bridging thiolate complex is characterized by X-ray crystallography, shedding light on a possible deactivation pathway.
Mudd, R. J., Young, P., Jordan-Hore, J., Rosair, G. M., & Lee, A-L. (2012). Gold(I)-catalyzed addition of thiols and thioacids to 3,3-disubstituted cyclopropenes. Journal of Organic Chemistry, 77(17), 7633-7639. https://doi.org/10.1021/jo300930c