Chlorination of Aliphatic Primary Alcohols Via Triphosgene-triethylamine Activation

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2012 Jul 12

PMID 22780451

Citations 10

Authors

Caitlan E Ayala

Andres Villalpando

Alex L Nguyen

Gregory T McCandless

Rendy Kartika

Affiliations

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Abstract

Activation of primary aliphatic alcohols with triphosgene and triethylamine mixtures afforded either alkyl chloride or diethylcarbamate products, and the switch in selectivity appeared to be driven by sterics. The reaction conditions to achieve this highly useful transformation were unexceptionally mild and readily tolerated by a wide range of sensitive functionalities.

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