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A Versatile Metal‐Free Intermolecular Aminochlorination of Alkenes
Author(s) -
Martínez Claudio,
Muñiz Kilian
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300880
Subject(s) - chemistry , intermolecular force , protonation , acetic acid , stoichiometry , structural isomer , metal , reaction conditions , combinatorial chemistry , organic chemistry , molecule , catalysis , ion
New reaction conditions for the rapid and productive intermolecular aminochlorination reaction of alkenes using a combination of chloramine‐T and a Brønstedt acid are described. Upon simple protonation of chloramine‐T, conditions for a mild and selective aminochlorination are obtained. In addition, the reaction can proceed to form either of the two possible regioisomers, depending on whether a stoichiometric amount of such an acid activator or acetic acid is used as solvent. The reaction is operative for all different classes of alkenes. A total of over 50 examples is presented to illustrate this concept.