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Rearrangement of Alkynyl Sulfoxides Catalyzed by Gold(I) Complexes

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journal contribution
posted on 2007-04-11, 00:00 authored by Nathan D. Shapiro, F. Dean Toste
A series of gold(I)-catalyzed rearrangement reactions of alkynyl sulfoxides are reported. Homopropargylsulfoxides are rearranged to benzothiepinones or benzothiopines, while α-thioenones are formed in the reaction of propargylsulfoxides. The proposed mechanism proceeds via an α-carbonyl gold−carbenoid intermediate formed through gold-promoted oxygen atom transfer from the sulfoxide to the alkyne.

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