Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 25, Pages 7152-7156Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201602569
Keywords
C-H functionalization; C-N coupling; copper catalysis; hypervalent iodine; imidazoles
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Funding
- Fundacio ICIQ
- MINECO [CTQ2013-46705-R, CTQ2014-54071-P]
- MINECO (Severo Ochoa Excellence Accreditation) [SEV-2013-0319]
- Generalitat de Catalunya [2014 SGR 1192]
- CELLEX Foundation through the CELLEX-ICIQ HTE platform
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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 lambda(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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