A General Strategy for Regiocontrol in Nickel-Catalyzed Reductive Couplings of Aldehydes and Alkynes

Hasnain A. Malik, Grant J. Sormunen and John Montgomery*

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

H. A. Malik, G. J. Sormunen, J. Montgomery, J. Am. Chem. Soc., 2010, 132, 6304-6305.

DOI: 10.1021/ja102262v

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Abstract

The complementary use of small cyclopropenylidene carbene ligands or highly hindered N-heterocyclic carbene ligands allows the regiochemical reversal in aldehyde-alkyne reductive couplings with unbiased internal alkynes, aromatic internal alkynes, conjugated enynes, or terminal alkynes.

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Ligand-Dependent Scope and Divergent Mechanistic Behavior in Nickel-Catalyzed Reductive Couplings of Aldehydes and Alkynes

G. M. Mahandru, G. Liu, J. Montgomery, J. Am. Chem. Soc., 2004, 126, 3698-3699.

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Key Words

Allylic Alcohols, Silanes, Multicomponent Reactions

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ID: J48-Y2010-1330