144150-91-4Relevant articles and documents
Influence of several parameters on the stereoselectivity of the 1,3-dienes synthesis through carbopalladation of allenes.
Friess, B.,Cazes, B.,Gore, J.
, p. 273 - 279 (2007/10/02)
The effects of the temperature and of the nature of solvent, phosphine ligand and carbon nucleophile on the stereoselectivity of the palladium-catalyzed process involving 1,2-decadiene and vinyl bromide and leading to 1,3-dienes have been studied.This reaction, which produces a 1:1 mixture of dienes in the conditions previously described (THF, Pd(dppe), anion of malonate) can be oriented either towards the E-isomer (75percent) by using acetonitrile or an hindered phosphine, or towards the Z-isomer (83percent) when a low-nucleophilic anion is involved.These results can be related to the relative stability and reactivity of both syn and anti ?-allyl complexes which are intermediates in the process.Keywords: ?-allylpalladium / carbopalladation / allenes / stereoselectivity / phosphorus ligand
