Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles

BJ Stokes, SM Opra, MS Sigman

Index: Stokes, Benjamin J.; Opra, Susanne M.; Sigman, Matthew S. Journal of the American Chemical Society, 2012 , vol. 134, # 28 p. 11408 - 11411

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Citation Number: 33

Abstract

The Pd (0)-catalyzed allylic cross-coupling of homoallylic tosylate substrates using boronic acids and pinacol esters is reported. The reaction uses 2-(4, 5-dihydro-2-oxazolyl) quinoline (quinox) as a ligand and is performed at ambient temperature. The scope of the reaction is broad in terms of both the boronate transmetalating reagent and the substrate and includes secondary tosylates. Mechanistic studies support an alkene-mediated SN2-type ...