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

Masatoshi Shibuya; Takuro Shibuta; Hayato Fukuda; Yoshiharu Iwabuchi

doi:10.1021/ol3021435

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

Masatoshi Shibuya, Takuro Shibuta, Hayato Fukuda, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

Tohoku University

Research output: Contribution to journal › Article › peer-review

29 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 language	English
Pages (from-to)	5010-5013
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	19
DOIs	https://doi.org/10.1021/ol3021435
Publication status	Published - 2012 Oct 5

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10.1021/ol3021435

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AU - Fukuda, Hayato

AU - Iwabuchi, Yoshiharu

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

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