The direct coupling reactions of organoboronic acids with propargylic and allenic alcohols have been achieved using palladium catalyst. The reaction of the propargylic alcohol with arylboronic acid in the presence of palladium catalyst affords the coupled allenic and propargylic compound. The ratio of both products can be controlled by changing substituents on the substrate, and variety of aryl-substituted allenes and propargylic compounds can be rationally synthesized. The reaction can also be applied to allenic alcohols. When the allenic alcohol was subjected to the reaction with arylboronic acid in the presence of catalytic amount of palladium complex, the reaction is completed within 1 h to afford a coupled diene. Various aryl-substituted dienes can be directly synthesized from the corresponding allenic alcohols with arylboronic acids in high yields.
