Oxidative hydroxylation mediated by alkoxysulfonium ions.

Research paper by Yosuke Y Ashikari, Toshiki T Nokami, Jun-ichi J Yoshida

Indexed on: 26 Jan '12Published on: 26 Jan '12Published in: Organic Letters


Oxidative hydroxylation of toluene derivatives via alkoxysulfonium ion intermediates was achieved by integration of anodic oxidation and hydrolysis to give benzyl alcohols which are also susceptible to oxidation. Alkenes were also oxidized to give 1,2-diols without overoxidation. The integration of electrochemical oxidative cyclization and hydrolysis was achieved using alkenes bearing a nitrogen atom in an appropriate position to give cyclic β-amino-substituted alcohols.