Metal-Free Reductive Cleavage of N-O Bonds in Weinreb Amides by an Organic Neutral Super-Electron Donor
Sylvain P. Y. Cutulic, John A. Murphy*, Hardeep Farwaha, Sheng-Ze Zhou, Ewan Chrystal
*WestCHEM, Department of Pure and Applied Chemistry,
University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, UK, Email: john.murphy
strath.ac.uk
S. P. Y. Cutulic, J. A. Murphy, H. Farwaha, S.-Z. Zhou, E. Chrystal, Synlett, 2008, 2132-2136.
DOI: 10.1055/s-2008-1078240
Abstract
Neutral organic super-electron donors can be used as reducing agents for the cleavage of N-O bonds in Weinreb amides. This methodology proved to be applicable to a large array of substrates to afford their reduced counterparts in good yields.
see article for more examples
proposed mechanism
S. P. Y. Cutulic, N. J. Findlay, S.-Z. Zhou, E. J. T. Chrystal, J. A. Murphy, J. Org. Chem., 2009, 74, 8713-8718.
Key Words
electron transfer, Weinreb amides, reduction, pyridinylidenes
ID: J60-Y2008-2290
