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Synlett 2008(14): 2132-2136  
DOI: 10.1055/s-2008-1078240
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Sylvain P. Y. Cutulica, John A. Murphy*a, Hardeep Farwahaa, Sheng-Ze Zhoua, Ewan Chrystalb
a WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, UK
Fax: +44(141)5484822; e-Mail: John.Murphy@strath.ac.uk;
b Syngenta, Jealott’s Hill International Research Centre, Bracknell RG42 6EY, UK
Further Information

Publication History

Received 2 June 2008
Publication Date:
31 July 2008 (online)

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Abstract

The scope of neutral organic super-electron donors as reducing agents has been extended to include the reductive 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 to excellent yields. The variation in reactivity within the set of tested amides is rationalised.

Key words

electron transfer - Weinreb amide - reduction - pyr­idinylidene

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