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Triphosgene-Amine Base Promoted Chlorination of Unactivated Aliphatic Alcohols

Andrés Villalpando, Caitlan E. Ayala, Christopher B. Watson and Rendy Kartika*

*Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, Louisiana 70803, United States, Email:

A. Villalpando, C. E. Ayala, C. B. Watson, R. Kartika, J. Org. Chem., 2013, 78, 3989-3996.

DOI: 10.1021/jo400341n (free Supporting Information)

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

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Chlorination of Aliphatic Primary Alcohols via Triphosgene-Triethylamine Activation

C. E. Ayala, A. Villalpando, A. L. Nguyen, G. T. McCandless, R. Kartika, Org. Lett., 2012, 14, 3676-3679.

Key Words

alkyl chlorides

ID: J42-Y2013-1010