An improved synthesis of 5-ethyl-4a-methyl-2-oxo-2,3,4,4a,7,8-hexahydronaphthalene and similar 1,3-dienes using palladium catalyzed cross-coupling methodology

Article abstract of DOI:10.1055/s-1995-4148

We report an efficient synthesis of 1,3-dienes from readily available enol triflates and vinyltributyltin using Pd₂(dba)₃ and triphenylarsine. Our approach allows for the preparation of these systems at room temperature and thus prevents isomerization to other isomeric dienes. The mild reaction conditions are attributed to the rate acceleration of the cross-coupling reaction due to the weak σ-donation of the triphenylarsine ligand on the palladium catalyst.