Development of an azanoradamantane-type nitroxyl radical catalyst for class-selective oxidation of alcohols

Ryusuke Doi, Masatoshi Shibuya, Tsukasa Murayama, Yoshihiko Yamamoto, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

The development of 1,5-dimethyl-9-azanoradamantane N-oxyl (DMN-AZADO; 1,5-dimethyl-Nor-AZADO, 2) as an efficient catalyst for the selective oxidation of primary alcohols in the presence of secondary alcohols is described. The compact and rigid structure of the azanoradamantane nucleus confers potent catalytic ability to DMN-AZADO (2). A variety of hindered primary alcohols such as neopentyl primary alcohols were efficiently oxidized by DMN-AZADO (2) to the corresponding aldehydes, whereas secondary alcohols remained intact. DMN-AZADO (2) also has high catalytic efficiency for one-pot oxidation from primary alcohols to the corresponding carboxylic acids in the presence of secondary alcohols and for oxidative lactonization from diols.

Original languageEnglish
Pages (from-to)401-413
Number of pages13
JournalJournal of Organic Chemistry
Volume80
Issue number1
DOIs
Publication statusPublished - 2015 Jan 2

ASJC Scopus subject areas

  • Organic Chemistry

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