Metal-free reductive cleavage of c-o sigma-bonds in acyloin derivatives by an organic neutral super-electron-donor

Cutulic, S.P.Y. and Findlay, N.J. and Zhou, S.Z. and Chrystal, E.J.T. and Murphy, J.A. (2009) Metal-free reductive cleavage of c-o sigma-bonds in acyloin derivatives by an organic neutral super-electron-donor. Journal of Organic Chemistry, 74 (22). pp. 8713-8718. ISSN 0022-3263

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Abstract

Neutral organic electron-donor 7, formally a pyridinylidene carbene dimer, effects reductive cleavage of C-O sigma-bonds in acyloin derivatives Ar(CO)CRR'OX (X = OAc, OPiv, OBz, OMs) and this represents the first cleavage of C-O sigma-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.