Revisiting Arene C(sp2)−H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a Spirocyclization Pathway

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Title
Revisiting Arene C(sp2)−H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a Spirocyclization Pathway
Author(s)
Yeongyu Hwang; Yoonsu Park; Yeong Bum Kim; Dongwook Kim; Sukbok Chang
Publication Date
2018-10
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.57, no.41, pp.13565 - 13569
Publisher
WILEY-V C H VERLAG GMBH
Abstract
Two mechanistic pathways, that is, electrocyclization and electrophilic aromatic substitution, are operative in most intramolecular C−H amination reactions proceeding by metal nitrenoid catalysis. Reported here is an alternative mechanistic scaffold leading to benzofused δ-lactams selectively. Integrated experimental and computational analysis revealed that the reaction proceeds by a key spirocyclization step followed by a skeletal rearrangement. Based on this mechanistic insight, a new synthetic route to spirolactams has been developed. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinhei
URI
https://pr.ibs.re.kr/handle/8788114/5306
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
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