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Triphosgene-amine base promoted chlorination of unactivated aliphatic alcohols.

ABSTRACT: Unactivated ?-branched primary and secondary aliphatic alcohols have been successfully transformed into their corresponding alkyl chlorides in high yields upon treatment with a mixture of triphosgene and pyridine in dichloromethane at reflux. These mild chlorination conditions are high yielding, stereospecific, and well tolerated by numerous sensitive functionalities. Furthermore, no nuisance waste products are generated in the course of the reactions.

SUBMITTER: Villalpando A

PROVIDER: S-EPMC4153350 | biostudies-literature | 2013 Apr

REPOSITORIES: biostudies-literature

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Triphosgene-amine base promoted chlorination of unactivated aliphatic alcohols.

Villalpando Andrés A Ayala Caitlan E CE Watson Christopher B CB Kartika Rendy R

The Journal of organic chemistry 20130329 8

Unactivated α-branched primary and secondary aliphatic alcohols have been successfully transformed into their corresponding alkyl chlorides in high yields upon treatment with a mixture of triphosgene and pyridine in dichloromethane at reflux. These mild chlorination conditions are high yielding, stereospecific, and well tolerated by numerous sensitive functionalities. Furthermore, no nuisance waste products are generated in the course of the reactions. ...[more]

PMID: 23496045

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