An Improved Synthesis of 5-Ethenyl-4a-methyl-2-oxo-2,3,4,4a,7,8-hexahydronaphthalene and Similar 1,3-Dienes using Palladium Catalyzed Cross-Coupling Methodology

Kollol Pal

doi:10.1055/s-1995-4148

Synthesis 1995; 1995(12): 1485-1487
DOI: 10.1055/s-1995-4148

short paper

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An Improved Synthesis of 5-Ethenyl-4a-methyl-2-oxo-2,3,4,4a,7,8-hexahydronaphthalene and Similar 1,3-Dienes using Palladium Catalyzed Cross-Coupling Methodology

Kollol Pal^*

^*Department of Medicinal Chemistry, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, Connecticut 06877-0368, USA, Fax +1(617)2250005

Abstract

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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.

cross coupling - enol triflate - 1,3-dienes

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