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

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

DOI: 10.1021/ja407749w (free Supporting Information)


Abstract

In regioselective methods for allene hydrosilylation, alkenylsilanes are produced via nickel catalysis with larger N-heterocyclic carbene (NHC) ligands, whereas allylsilanes are produced via palladium catalysis with smaller NHC ligands. These complementary methods allow either regioisomeric product to be obtained with exceptional regiocontrol.

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

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


Key Words

vinylsilanes, allylsilanes


ID: J48-Y2013