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Dual role of carboxylic acid additive: Mechanistic studies and implication for the asymmetric C-H amidation Dedicated to Professor Yoshiaki Nakao on his receipt of the Tetrahedron Young Investigator Award

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Title
Dual role of carboxylic acid additive: Mechanistic studies and implication for the asymmetric C-H amidation Dedicated to Professor Yoshiaki Nakao on his receipt of the Tetrahedron Young Investigator Award
Author(s)
Donghyeon Gwon; Sehoon Park; Sukbok Chang
Subject
C-H amidation, Phosphoryl compounds, Acid additive effects, Mechanistic study, Asymmetric induction
Publication Date
2015-07
Journal
TETRAHEDRON, v.71, no.26-27, pp.4504 - 4511
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Abstract
Acid additive effects in the Ir-catalyzed CeH amidation of arylphosphoryl compounds were examined. Structure of catalytically active metal species was elucidated: mono-cationic iridium catalyst [Cp*Ir(- III)(OAc)](NTf2) being mainly responsible for the CeH bond activation. Mechanistic studies revealed a dual role of carboxylic acid additive operating both in the generation of an iridacyclic intermediate and in the protodemetalation process to release amidated products. The fact that asymmetric CeH amidation was achieved albeit in moderate enantioselectivity by using chiral carboxylic acid supports our proposal especially with regard to the role of acid additive. © 2015 Elsevier Ltd. All rights reserved
URI
https://pr.ibs.re.kr/handle/8788114/1972
DOI
10.1016/j.tet.2015.02.065
ISSN
0040-4020
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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