NiH-Catalyzed Proximal-Selective Hydroamination of Unactivated Alkenes

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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.
Publisher
AMER CHEMICAL SOC
Issue Date
2020-11
Language
English
Article Type
Article
Citation

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.142, no.48, pp.20470 - 20480

ISSN
0002-7863
DOI
10.1021/jacs.0c10333
URI
http://hdl.handle.net/10203/279381
Appears in Collection
CH-Journal Papers(저널논문)
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