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Regioselective Allene Hydroarylation via One-Pot Allene Hydrosilylation/Pd-Catalyzed Cross-Coupling

Zachary D. Miller and John Montgomery*

*Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, United States, Email: jmontgumich.edu

Z. D. Miller, J. Montgomery, Org. Lett., 2014, 16, 5486-5489.

DOI: 10.1021/ol502766q (free Supporting Information)


Abstract

A one-pot regioselective allene hydrosilylation/Pd(0)-catalyzed cross-coupling protocol affords functionalized 1,1-disubstituted alkenes with excellent regiocontrol. The regioselectivity of this hydroarylation is primarily governed by N-heterocyclic carbene (NHC) ligand identity in the hydrosilylation step and is preserved in the subsequent cross-coupling reaction.

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Regioselective Allene Hydrosilylation Catalyzed by N-Heterocyclic Carbene Complexes of Nickel and Palladium

Z. D. Miller, W. Li, T. R. Belderrain, J. Montgomery, J. Am. Chem. Soc., 2013, 135, 15282-15285.


Key Words

vinyl silanes, Hiyama coupling, olefination


ID: J54-Y2014