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Atmosphere‐ and Temperature‐Controlled Regioselective Aminobromination of Olefins
Author(s) -
Yu Wesley Zongrong,
Cheng Yi An,
Wong Ming Wah,
Yeung YingYeung
Publication year - 2017
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.201600821
Subject(s) - regioselectivity , chemistry , atmosphere (unit) , catalysis , amine gas treating , argon , organic chemistry , photochemistry , thermodynamics , physics
A complete switch of regioselectivity in the aminobromination of olefins is realized from delicate changes in the reaction temperature from 25 °C to 40 °C and the atmosphere from air to argon, under catalyst‐free conditions. The resulting α‐bromoamides can be transformed easily to high‐value compounds (e.g., Clobenzorex). Mechanistic studies revealed that the reaction went through a radical pathway governed by in‐situ generated bromo(tosyl)amine (TsNHBr).