NH‐Heterocyclic Aryliodonium Salts and their Selective Conversion into N1‐Aryl‐5‐iodoimidazoles |
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| Authors: | Yichen Wu Dr. Susana Izquierdo Dr. Pietro Vidossich Prof. Dr. Agustí Lledós Dr. Alexandr Shafir |
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| Affiliation: | 1. Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Tarragona, Spain;2. Departament de Química, Universitat Autònoma de Barcelona, Cerdanyola del Vallès, Spain |
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| Abstract: | 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 N1‐aryl‐5‐iodoimidazoles. Iodine acts as a “universal” placeholder poised for replacement by aryl substituents. These new λ3‐iodanes are produced by treating the NH‐imidazole with ArI(OAc)2, and are converted to N1‐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. |
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| Keywords: | C− H functionalization C− N coupling copper catalysis hypervalent iodine imidazoles |
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