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Palladium-Catalyzed Allylic Cross-Coupling Reactions of Primary and Secondary Homoallylic Electrophiles

Benjamin J. Stokes, Susanne M. Opra and Matthew S. Sigman*

*Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, United States, Email: sigmanchem.utah.edu

B. J. Stokes, S. M. Opra, M. S. Sigman, J. Am. Chem. Soc., 2012, 134, 11408-11411.

DOI: 10.1021/ja305403s (free Supporting Information)


Abstract

The Pd(0)-catalyzed allylic cross-coupling of homoallylic tosylate substrates using boronic acids and pinacol esters 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 and the tosylate, that includes secondary tosylates.

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Key Words

allylation (of arenes, alkenes)


ID: J48-Y2012-2310