Metal-free reductive cleavage of C−O σ-bonds in acyloin derivatives by an organic neutral super-electron-donor

Cutulic, S. P.Y., Findlay, N. J. , Zhou, S.-Z., Chrystal, E. J.T. and Murphy, J. A. (2009) Metal-free reductive cleavage of C−O σ-bonds in acyloin derivatives by an organic neutral super-electron-donor. Journal of Organic Chemistry, 74(22), pp. 8713-8718. (doi:10.1021/jo901815t)

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Abstract

Neutral organic electron-donor 7, formally a pyridinylidene carbene dimer, effects reductive cleavage of C−O σ-bonds in acyloin derivatives Ar(CO)CRR′OX (X = OAc, OPiv, OBz, OMs) and this 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 counterparts were isolated in good to excellent yields. For certain substrates, donor 7 behaves as a base, effecting condensation reactions with some acetate ester derivatives of acyloins, leading to butenolides. The variation in reactivity among the different substrates was rationalized.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Findlay, Mr Neil
Authors: Cutulic, S. P.Y., Findlay, N. J., Zhou, S.-Z., Chrystal, E. J.T., and Murphy, J. A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:American Chemical Society
ISSN:0022-3263
ISSN (Online):1520-6904

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