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NH‐Heterocyclic Aryliodonium Salts and their Selective Conversion into N 1‐Aryl‐5‐iodoimidazoles
Author(s) -
Wu Yichen,
Izquierdo Susana,
Vidossich Pietro,
Lledós Agustí,
Shafir Alexandr
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201602569
Subject(s) - aryl , steric effects , imidazole , chemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , alkyl
The synthesis of N ‐arylimidazoles substituted at the sterically encumbered 5‐position is a challenge for modern synthetic approaches. A new family of imidazolyl aryliodonium salts is reported, which serve as a stepping stone on the way to selective formation of N 1‐aryl‐5‐iodoimidazoles. Iodine acts as a “universal” placeholder poised for replacement by aryl substituents. These new λ 3 ‐iodanes are produced by treating the NH ‐imidazole with ArI(OAc) 2 , and are converted to N 1‐aryl‐5‐iodoimidazoles by a selective copper‐catalyzed aryl migration. The method tolerates a variety of aryl fragments and is also applicable to substituted imidazoles.