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Highly Robust Iron Catalyst System for Intramolecular C(sp(3))-H Amidation Leading to gamma-Lactams

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Title
Highly Robust Iron Catalyst System for Intramolecular C(sp(3))-H Amidation Leading to gamma-Lactams
Author(s)
Jeonguk Kweon; Sukbok Chang
Publication Date
2021-02
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.60, no.6, pp.2909 - 2914
Publisher
WILEY-V C H VERLAG GMBH
Abstract
Disclosed here is the use of an iron catalyst system for an intramolecular C-H amidation toward gamma-lactam synthesis from dioxazolone precursors. (Phthalocyanine)(FeCl)-Cl-III was found to catalyze this cyclization with extremely high turnover numbers of up to 47 000 under mild and aerobic conditions. On the basis of experimental and computational mechanistic studies, the reaction is suggested to proceed by a stepwise radical pathway involving fast hydrogen atom abstraction followed by radical rebound. A plausible origin for the high turnover numbers along with air-compatibility is also rationalized.
URI
https://pr.ibs.re.kr/handle/8788114/9206
DOI
10.1002/anie.202013499
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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