2001•Advanced Synthesis & CatalysisRequires access

Remarkable Ligand Effects in Regioselective Palladium-Catalysed Allylic Substitution Reactions

Lara Acemoglu, Jonathan M. J. Williams

Abstract

The use of tricyclohexylphosphine (and related phosphines) in palladium-catalysed allylic substitution reactions enables the selective conversion of branched allylic acetates into the branched substitution products (up to 120:1 regioselectivity). Linear allylic acetates do not show the same selectivity for the branched substitution products, thereby demonstrating a memory effect.

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Available abstract

Key concepts: Allylic rearrangement, Chemistry, Regioselectivity, Tricyclohexylphosphine, Palladium, Substitution reaction, Substitution (logic), Selectivity