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NiH-Catalyzed Proximal-Selective Hydroamination of Unactivated Alkenes

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Title
NiH-Catalyzed Proximal-Selective Hydroamination of Unactivated Alkenes
Author(s)
Jinwon Jeon; Changseok Lee; Huiyeong Seo; Sungwoo Hong
Publication Date
2020-12
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.142, no.48, pp.20470 - 20480
Publisher
AMER CHEMICAL SOC
Abstract
© 2020 American Chemical Society. Reported herein is a modular, NiH-catalyzed system capable of proximal-selective hydroamination of unactivated alkenes with diverse amine sources. The key to the successful implementation of this approach is the promotion of NiH insertion into even highly substituted olefins via coordination of the bidentate directing group to the nickel complex. A wide range of primary and secondary amines can be installed in both internal and terminal unactivated alkenes with excellent regiocontrol under the optimized reaction conditions. This protocol is flexible and general for the preparation of a variety of valuable β- and γ-amino acid building blocks that would otherwise be difficult to synthesize. The utility of this transformation was further demonstrated by the site-selective late-stage modification of complex and medicinally relevant molecules. Combined experimental and computational studies illuminate the detailed reaction mechanism
URI
https://pr.ibs.re.kr/handle/8788114/7510
DOI
10.1021/jacs.0c10333
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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