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Deoxygenative C-C Bond-Forming Processes via a Net Four-Electron Reductive Coupling

David P. Todd, Benjamin B. Thompson, Alex J. Nett and John Montgomery*

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

D. P. Todd, B. B. Thompson, A. J. Nett, J. Montgomery, J. Am. Chem. Soc., 2015, 137, 12788-12791.

DOI: 10.1021/jacs.5b08448 (free Supporting Information)



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Abstract

A nickel-catalyzed coupling of enones or enals with alkynes in the presence of silane and titanium alkoxide reductants provides direct access to skipped diene products via a net four-electron reductive coupling and deoxygenation. A new class of well-defined nickel(0) precatalysts bearing an unhindered N-heterocyclic carbene ligand is essential for the efficiency of the transformation.

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Key Words

1,4-dienes, TES


ID: J48-Y2015