Highly chemo- and regioselective thiocarbonylation of conjugated enynes with thiols and carbon monoxide catalyzed by palladium complexes: An efficient and atom-economical access to 2-(phenylthiocarbonyl)-1,3-dienes
Wj. Xiao et al., Highly chemo- and regioselective thiocarbonylation of conjugated enynes with thiols and carbon monoxide catalyzed by palladium complexes: An efficient and atom-economical access to 2-(phenylthiocarbonyl)-1,3-dienes, J ORG CHEM, 64(6), 1999, pp. 2080-2084
The reaction of 1, 3-conjugated enynes bearing a terminal triple bond with
thiols and carbon monoxide in the presence of catalytic quantities of Pd(OA
c)(2) (3 mol %) and 1,3-bis(diphenylphosphino)propane (6 mol %) in THF at 1
10 degrees C gave 2-(phenylthiocarbonyl)-1,3-dienes in moderate to good yie
lds. The thiocarbonylation takes place with high chemo- and regioselectivit
y, with the attack by the phenylthiocarbonyl group occurring exclusively at
carbon-2 of the 1,3-conjugated enyne.