Highly efficient, organocatalytic aerobic alcohol oxidation

Masatoshi Shibuya; Yuji Osada; Yusuke Sasano; Masaki Tomizawa; Yoshiharu Iwabuchi

doi:10.1021/ja110940c

Highly efficient, organocatalytic aerobic alcohol oxidation

J Am Chem Soc. 2011 May 4;133(17):6497-500. doi: 10.1021/ja110940c. Epub 2011 Apr 7.

Authors

Masatoshi Shibuya¹, Yuji Osada, Yusuke Sasano, Masaki Tomizawa, Yoshiharu Iwabuchi

Affiliation

¹ Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama 6-3, Sendai 980-8578, Japan.

PMID: 21473575
DOI: 10.1021/ja110940c

Abstract

5-Fluoro-2-azaadamantane N-oxyl (5-F-AZADO) realizes a simple, organocatalytic aerobic alcohol oxidation system that has a wide scope under mild conditions at ambient pressure and temperature and is weakly acidic and halogen- and transition-metal-free. The oxoammonium nitrate (5-F-AZADO(+)NO(3)(-)) works as a bifunctional catalyst of 5-F-AZADO and NO(x) that enables the catalytic aerobic oxidation of alcohols by itself (a metal-salt-free system).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adamantane / analogs & derivatives
Adamantane / chemistry
Alcohols / chemistry*
Catalysis
Cyclic N-Oxides / chemistry
Oxidation-Reduction

Substances

2-azaadamantane N-oxyl
Alcohols
Cyclic N-Oxides
Adamantane