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

S.P.Y. Cutulic, N.J. Findlay, S.Z. Zhou, E.J.T. Chrystal, J.A. Murphy

Research output: Contribution to journalArticlepeer-review

48 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)8713-8718
Number of pages5
JournalJournal of Organic Chemistry
Volume74
Issue number22
Publication statusPublished - 20 Nov 2009

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