Organic letters

Copper-Catalyzed Remote sp3 C− H Chlorination of Alkyl Hydroperoxides

R Kundu, ZT Ball

Index: Kundu, Rituparna; Ball, Zachary T. Organic Letters, 2010 , vol. 12, # 11 p. 2460 - 2463

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Citation Number: 24

Abstract

A copper-catalyzed methodology to functionalize remote sp3 C− H bonds in alkyl hydroperoxides is presented. The atom-transfer chlorination utilizes simple ammonium chloride salts as the chlorine source, and the internal redox process requires no external redox reagents.

 Related Synthetic Route
2-hydroperoxyoctane Structure

32956-90-4

2-hydroperoxyoctane

~26%

2-Octanol Structure

4128-31-8

2-Octanol

5-chloro-2-octanol Structure

58705-87-6

5-chloro-2-octanol

2-Octanone Structure

111-13-7

2-Octanone

n--decyl hydroperoxide Structure

4225-91-6

n--decyl hydrop...

~8%

2-Octanol Structure

4128-31-8

2-Octanol

5-chloro-2-octanol Structure

58705-87-6

5-chloro-2-octanol

2-Octanone Structure

111-13-7

2-Octanone

Octane, 2-chloro- Structure

628-61-5

Octane, 2-chloro-

~21%

2-hydroperoxyoctane Structure

32956-90-4

2-hydroperoxyoctane


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