Gold-Catalyzed Oxidative Cyclization/C-C Bond Cleavage of Ynones with External Nucleophiles: Synthesis of Linear Functionalized N -Tosylamides.

A gold-catalyzed oxidative cyclization/nucleophilic addition/C-C bond cleavage reaction of ynones with various nucleophiles has been developed. This methodology allows for the formation of highly functionalized linear N -Ts amides with broad substrate scope, high efficiency, and general tolerance of functional groups. A wide range of nucleophiles such as alcohols, water, and amines including aryl and alkyl amines are compatible with the current method. The C-C triple bond cleavage of the ynone substrate was observed during the process.