Chlorination of Aliphatic Primary Alcohols via Triphosgene–Triethylamine Activation

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...

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 14; pp. 3676 - 3679
Main Authors Ayala, Caitlan E, Villalpando, Andres, Nguyen, Alex L, McCandless, Gregory T, Kartika, Rendy
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.07.2012
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PHOSGENE
SAFE
AMINES
EFFICIENT
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol301520d