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

Gireesh M. Mahandru, Gang Liu and John Montgomery*

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

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

DOI: 10.1021/ja049644n

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Abstract

A new procedure for catalytic reductive coupling of aldehydes and alkynes uses Ni(COD)₂ with an imidazolium carbene ligand as the catalyst and triethylsilane as the reducing agent.

see article for more examples

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

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

Highly Diastereoselective Preparation of anti-1,2-Diols by Catalytic Addition of Alkynylsilanes to α-Silyloxyaldehydes

K. Sa-ei, J. Montgomery, Org. Lett., 2006, 8, 4441-4443.

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Key Words

Allylic Alcohols, Silyl Ethers, Triethylsilane, Multicomponent Reactions

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ID: J48-Y2004-1430