2-azaadamantane N-oxyl (AZADO) and 1-Me-AZADO: highly efficient organocatalysts for oxidation of alcohols

Masatoshi Shibuya; Masaki Tomizawa; Iwao Suzuki; Yoshiharu Iwabuchi

doi:10.1021/ja0620336

2-azaadamantane N-oxyl (AZADO) and 1-Me-AZADO: highly efficient organocatalysts for oxidation of alcohols

J Am Chem Soc. 2006 Jul 5;128(26):8412-3. doi: 10.1021/ja0620336.

Authors

Masatoshi Shibuya¹, Masaki Tomizawa, Iwao Suzuki, Yoshiharu Iwabuchi

Affiliation

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

PMID: 16802802
DOI: 10.1021/ja0620336

Abstract

Development of a stable nitroxyl radical class of catalysts, 2-azaadamantane N-oxyl (AZADO) and 1-Me-AZADO, for highly efficient oxidation of alcohols is described. AZADO and 1-Me-AZADO exhibit superior catalytic proficiency to TEMPO, converting various sterically hindered alcohols to the corresponding carbonyl compounds in excellent yields.

Publication types

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

MeSH terms

Adamantane / analogs & derivatives*
Adamantane / chemistry
Alcohols / chemistry*
Aldehydes / chemical synthesis*
Aldehydes / chemistry
Catalysis
Cyclic N-Oxides / chemistry*
Free Radicals / chemistry
Molecular Structure
Oxidation-Reduction
Stereoisomerism

Substances

2-aza-1-methyladamantane N-oxyl
2-azaadamantane N-oxyl
Alcohols
Aldehydes
Cyclic N-Oxides
Free Radicals
Adamantane