Nitroxyl radical/PhI(OAc)2: One-pot oxidative cleavage of vicinal diols to (di)carboxylic acids

Masatoshi Shibuya, Takuro Shibuta, Hayato Fukuda, Yoshiharu Iwabuchi

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

A mild and user-friendly one-pot oxidative cleavage of vicinal diols to their corresponding (di)carboxylic acids using AZADOs and PhI(OAc)2 is described. 1,2-Diols and 2,3-diols as well as 1,2,3-triol gave one- or two-carbon-unit-shorter carboxylic acids. Internal vicinal diols also smoothly underwent one-pot oxidative cleavage to afford the corresponding dicarboxylic acids. Cyclic vicinal diols are converted to their corresponding open-form dicarboxylic acids.

Original languageEnglish
Pages (from-to)5010-5013
Number of pages4
JournalOrganic letters
Volume14
Issue number19
DOIs
Publication statusPublished - 2012 Oct 5

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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