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Metal-Free Reductive Cleavage of C-O σ-bonds in Acyloin Derivatives by an Organic Neutral Super-Electron-Donor

Sylvain P. Y. Cutulic, Neil J. Findlay, Sheng-Ze Zhou, Ewan J. T. Chrystal and John A. Murphy*

*WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, UK, Email: john.murphystrath.ac.uk

S. P. Y. Cutulic, N. J. Findlay, S.-Z. Zhou, E. J. T. Chrystal, J. A. Murphy, J. Org. Chem., 2009, 74, 8713-8718.

DOI: 10.1021/jo901815t (free Supporting Information)


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Abstract

A pyridinylidene carbene dimer effects reductive cleavage of C-O σ-bonds in acyloin derivatives, which represents the first cleavage of C-O σ-bonds by a neutral organic electron-donor. The methodology is applicable to a large array of substrates and the reduced products were isolated in good to excellent yields.

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proposed mechanism



Metal-Free Reductive Cleavage of N-O Bonds in Weinreb Amides by an Organic Neutral Super-Electron Donor

S. P. Y. Cutulic, J. A. Murphy, H. Farwaha, S.-Z. Zhou, E. Chrystal, Synlett, 2008, 2132-2136.


Key Words

electron transfer, acyloins, deoxygenation, pyridinylidenes


ID: J42-Y2009-3320