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Chlorination of Aliphatic Primary Alcohols via Triphosgene-Triethylamine Activation

Caitlan E. Ayala, Andres Villalpando, Alex L. Nguyen, Gregory T. McCandless and Rendy Kartika*

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

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

DOI: 10.1021/ol301520d (free Supporting Information)

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Activation of primary aliphatic alcohols with triphosgene and triethylamine mixtures afforded either alkyl chloride or diethylcarbamate products driven by sterics. The reaction conditions were unexceptionally mild and readily tolerated by a wide range of sensitive functionalities.

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Triphosgene-Amine Base Promoted Chlorination of Unactivated Aliphatic Alcohols

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

Key Words

alkyl chlorides

ID: J54-Y2012-2320