Oxidation of alcohols to carbonyl compounds with diisopropyl azodicarboxylate catalyzed by nitroxyl radicals

Masaki Hayashi; Masatoshi Shibuya; Yoshiharu Iwabuchi

doi:10.1021/jo300088b

Oxidation of alcohols to carbonyl compounds with diisopropyl azodicarboxylate catalyzed by nitroxyl radicals

Masaki Hayashi, Masatoshi Shibuya, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

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

68 Citations (Scopus)

Abstract

A nitroxyl-radical-catalyzed oxidation of alcohols using diisopropyl azodicarboxylate (DIAD) as the terminal oxidantis reported. A variety of primary and secondary alcohols including aliphatic, benzylic, and allylic alcohols are efficiently oxidized to their corresponding aldehydes and ketones without overoxidation to carboxylic acid. 1,2-Diols are oxidized to hydroxyl ketones or diketones depending on the amount of DIAD used.

Original language	English
Pages (from-to)	3005-3009
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	77
Issue number	6
DOIs	https://doi.org/10.1021/jo300088b
Publication status	Published - 2012 Mar 16

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10.1021/jo300088b

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abstract = "A nitroxyl-radical-catalyzed oxidation of alcohols using diisopropyl azodicarboxylate (DIAD) as the terminal oxidantis reported. A variety of primary and secondary alcohols including aliphatic, benzylic, and allylic alcohols are efficiently oxidized to their corresponding aldehydes and ketones without overoxidation to carboxylic acid. 1,2-Diols are oxidized to hydroxyl ketones or diketones depending on the amount of DIAD used.",

author = "Masaki Hayashi and Masatoshi Shibuya and Yoshiharu Iwabuchi",

year = "2012",

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AU - Hayashi, Masaki

AU - Shibuya, Masatoshi

AU - Iwabuchi, Yoshiharu

PY - 2012/3/16

Y1 - 2012/3/16

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AB - A nitroxyl-radical-catalyzed oxidation of alcohols using diisopropyl azodicarboxylate (DIAD) as the terminal oxidantis reported. A variety of primary and secondary alcohols including aliphatic, benzylic, and allylic alcohols are efficiently oxidized to their corresponding aldehydes and ketones without overoxidation to carboxylic acid. 1,2-Diols are oxidized to hydroxyl ketones or diketones depending on the amount of DIAD used.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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Oxidation of alcohols to carbonyl compounds with diisopropyl azodicarboxylate catalyzed by nitroxyl radicals

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