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Upon exposure to a ruthenium(0) catalyst, N-benzyl-3-hydroxy-2-oxindoles react with diverse alkynes to form products of C-H vinylation with complete control of regioselectivity and olefin geometry. This method contributes to a growing body of catalytic processes that enable direct conversion of lower alcohols to higher alcohols in the absence of stoichiometric organometallic reagents.

Ruthenium(0)-Catalyzed C–C Coupling of Alkynes and 3-Hydroxy-2-oxindoles: Direct C–H Vinylation of Alcohols