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

…, SZ Zhou, EJT Chrystal, JA Murphy

Index: Murphy, John A.; Schoenebeck, Franziska; Findlay, Neil J.; Thomson, Douglas W.; Zhou, Sheng-ze; Garnier, Jean Journal of the American Chemical Society, 2009 , vol. 131, p. 6475 - 6479

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Citation Number: 42

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 ...