Rh(i)-Catalyzed coupling of 2-bromoethyl aryldiazoacetates with tertiary propargyl alcohols through carbene migratory insertion

Abstract

A Rh(I)-catalyzed cross-coupling of 2-bromoethyl aryldiazoacetates with tertiary propargyl alcohols has been successfully achieved. This reaction follows a reaction sequence which involves C–C bond cleavage, Rh(I) carbene formation, carbene migratory insertion and nucleophilic substitution to achieve the construction of C(sp²)–C(sp) and C–O bonds. The products feature both enyne and ketene acetal moieties, which have been widely used as building blocks in organic synthesis and polymer science.