Abstract
The performance of nickel–phosphine and palladium–phosphine catalytic systems for model coupling reactions of allyl alcohol ( 1) with soft nucleophiles such as diethylamine ( 2), some active methylene compounds ( 4) or 1 itself in the formation of diallylether ( 7) are reported. It is shown that for a number of reactions, particularly the amination of 1, nickel catalysts are much more active than comparable palladium systems. However, Ni-catalytic species are more sensitive than the corresponding Pd ones, so that catalyst poisoning prevents some reactions to go to completion. The detection of allylbenzene ( 8) as a by-product in the etherification and amination reactions of 1 together with a 31 P NMR study has allowed to highlight a degradation pathway involving the cleavage of a phosphorus–carbon bond in a Ni-dppb intermediate.
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