Open AccessTriphosgene–Amine Base Promoted Chlorination of Unactivated Aliphatic Alcohols
Author(s) -
Andrés Villalpando,
Caitlan E. Ayala,
Christopher B. Watson,
Rendy Kartika
Publication year - 2013
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/jo400341n
Subject(s) - triphosgene , dichloromethane , stereospecificity , amine gas treating , organic chemistry , primary (astronomy) , alkyl , chemistry , pyridine , base (topology) , catalysis , mathematics , solvent , mathematical analysis , physics , astronomy , phosgene
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.