Cleavage of C-C and C-O Bonds to Form C-C Bonds: Direct Cross-Coupling between Acetylenic Alcohols and Benzylic Carbonates

A palladium-catalyzed cross-coupling reaction between C(sp) and C(sp(3)) centers was achieved in excellent yields via C-C bond cleavage and C-O bond cleavage. This procedure uses relatively stable acetylenic alcohols as reactants instead of unstable/volatile terminal alkynes. The use of benzylic carbonates also avoids the involvement of benzyl halides, making this method more practical in synthesis. Ligands play an important role in the procedure and K2CO3 accelerates the reaction.