A novel palladium-catalyzed intramolecular redox reaction

Org Lett. 2001 May 17;3(10):1495-7. doi: 10.1021/ol015813m.

Abstract

[reaction: see text] A new type of palladium-catalyzed redox reaction is described, forming enones from 2-(2-bromobenzyl)-ketones with an overall loss of HBr. The scope and limitations of the reaction are demonstrated by a series of cyclic and acyclic substrates. The mechanism most probably involves the formation of an intramolecular arylpalladium enolate and is related to the oxidation of silyl enol ethers with palladium acetate.