DEVELOPMENT OF EFFICIENT ORGANIC SYNTHESIS INVOLVING ORGANOBORANE AND ORGANOZINC PROMOTED BY TRANSITION METAL CATALYSIS

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Triethylborane activates allylic alcohols to formπ-allylpalladium key intermediates by oxidative addition of Pd(0) toward allylic C-O bonds and achieves amphiphilic allylations. Pd catalyzes three-component coupling reaction of allylic alcohol, terminal alkyne, and organoborane to provide(E)-1-substituted 2-alkyl-1, 4-pentadiene involving geminal allylation and alkylation at the acetylenic terminal carbon. Bis-diene undergoes the similar multi-component coupling reaction with acetylene and organoborane involving cyclization of bis.π-allypalladium to form trans-allyl pentadienyl cyclic and hetrocyclic compounds. Furthermore, a combination of Pd catalyst and triethylborane effectively promotes 3-hydroxy-4-pentenoic acid to undergoβ-decarboxylative C-C bond cleavage reaction viaβ-vinyloxapalladacyclopentanone to provide conjugated diene and carbon dioxide.