AI Article Synopsis
- The article discusses the challenges in synthesizing N-arylimidazoles, particularly at the 5-position.
- A new family of imidazolyl aryliodonium salts is introduced, facilitating the selective formation of N1-aryl-5-iodoimidazoles, using iodine as a placeholder for aryl groups.
- The synthesis method involves treating NH-imidazole with ArI(OAc)2 and utilizes copper-catalyzed aryl migration, allowing for various aryl fragments and substituted imidazoles.
Article 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 λ(3) -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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| http://dx.doi.org/10.1002/anie.201602569 | DOI Listing |
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