A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids

Mangzhu Zhao; Jing Li; Zhiguo Song; Richard Desmond; David M. Tschaen; Edward J.J. Grabowski; Paul J. Reider

doi:10.1016/S0040-4039(98)00987-3

A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids

Mangzhu Zhao, Jing Li, Zhiguo Song, Richard Desmond, David M. Tschaen, Edward J.J. Grabowski, Paul J. Reider

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

209 Scopus citations

Abstract

A novel CrO₃ catalyzed oxidation of primary alcohols to the carboxylic acids is reported. The oxidation proceeds smoothly with only 1-2 mol % of CrO₃ and 2.5 equivalents of H₃IO₆ in wet MeCN to give the carboxylic acids in excellent yield. No significant racemization is observed for alcohols with adjacent chiral centers. Secondary alcohols are cleanly oxidized to ketones.

Original language	English (US)
Pages (from-to)	5323-5326
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	30
DOIs	https://doi.org/10.1016/S0040-4039(98)00987-3
State	Published - Jul 23 1998
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Alcohols
Catalysis
Chromium
Oxidation

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10.1016/S0040-4039(98)00987-3

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title = "A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids",

abstract = "A novel CrO3 catalyzed oxidation of primary alcohols to the carboxylic acids is reported. The oxidation proceeds smoothly with only 1-2 mol % of CrO3 and 2.5 equivalents of H3IO6 in wet MeCN to give the carboxylic acids in excellent yield. No significant racemization is observed for alcohols with adjacent chiral centers. Secondary alcohols are cleanly oxidized to ketones.",

keywords = "Alcohols, Catalysis, Chromium, Oxidation",

author = "Mangzhu Zhao and Jing Li and Zhiguo Song and Richard Desmond and Tschaen, {David M.} and Grabowski, {Edward J.J.} and Reider, {Paul J.}",

year = "1998",

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day = "23",

doi = "10.1016/S0040-4039(98)00987-3",

language = "English (US)",

volume = "39",

pages = "5323--5326",

journal = "Tetrahedron Letters",

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number = "30",

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TY - JOUR

T1 - A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids

AU - Zhao, Mangzhu

AU - Li, Jing

AU - Song, Zhiguo

AU - Desmond, Richard

AU - Tschaen, David M.

AU - Grabowski, Edward J.J.

AU - Reider, Paul J.

PY - 1998/7/23

Y1 - 1998/7/23

N2 - A novel CrO3 catalyzed oxidation of primary alcohols to the carboxylic acids is reported. The oxidation proceeds smoothly with only 1-2 mol % of CrO3 and 2.5 equivalents of H3IO6 in wet MeCN to give the carboxylic acids in excellent yield. No significant racemization is observed for alcohols with adjacent chiral centers. Secondary alcohols are cleanly oxidized to ketones.

AB - A novel CrO3 catalyzed oxidation of primary alcohols to the carboxylic acids is reported. The oxidation proceeds smoothly with only 1-2 mol % of CrO3 and 2.5 equivalents of H3IO6 in wet MeCN to give the carboxylic acids in excellent yield. No significant racemization is observed for alcohols with adjacent chiral centers. Secondary alcohols are cleanly oxidized to ketones.

KW - Alcohols

KW - Catalysis

KW - Chromium

KW - Oxidation

UR - http://www.scopus.com/inward/record.url?scp=0032560829&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032560829&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(98)00987-3

DO - 10.1016/S0040-4039(98)00987-3

M3 - Article

AN - SCOPUS:0032560829

SN - 0040-4039

VL - 39

SP - 5323

EP - 5326

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -

A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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