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Indole‐ and Pyrrole‐BX: Bench‐Stable Hypervalent Iodine Reagents for Heterocycle Umpolung
Author(s) -
Caramenti Paola,
Nicolai Stefano,
Waser Jerome
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703723
Subject(s) - hypervalent molecule , reagent , umpolung , indole test , chemistry , pyrrole , combinatorial chemistry , reactivity (psychology) , catalysis , iodine , lewis acids and bases , organic chemistry , ruthenium , nucleophile , medicine , alternative medicine , pathology
The one‐step synthesis of the bench‐stable hypervalent iodine reagents IndoleBX and PyrroleBX using mild Lewis acid catalyzed conditions is reported. The new reagents are stable up to 150 °C and were applied in the C−H arylation of unactivated arenes using either rhodium or ruthenium catalysts. A broad range of heterocyclic systems of high interest for synthetic and medicinal chemistry was accessed in high yields. The developed C−H functionalization could not be achieved using reported reagents or methods, highlighting the unique reactivity of Indole‐ and Pyrrole‐BX.