Gold(I)-catalyzed addition of thiols and thioacids to 3,3-disubstituted cyclopropenes |
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Authors: | Richard J Mudd Paul C Young James A Jordan-Hore Georgina M Rosair Ai-Lan Lee |
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Institution: | Institute of Chemical Sciences, Heriot-Watt University , Edinburgh, EH14 4AS, United Kingdom. |
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Abstract: | 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. |
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