A detailed study of chemoselective palladium-based phosphine catalysts with 2-B(pin) allylic acetates is described. The different palladium catalyst and reaction conditions enable orthogonal reactivity involving allylic substitution, Suzuki cross-coupling, or allenes formation. The variables used to control chemoselectivity include the nature of the nucleophile, aryl halide, base, solvent, and reaction temperature. We have also examined the scope with 2-B(pin) allylic acetates, benzoates, and carbonates in the presence of palladium catalysts.

Diverse chemoselectivity with bifunctional 2-B(pin) allylic acetate templates

244th National Meeting (2012)

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