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γ-Selective C(sp3)–H amination via controlled migratory hydroamination

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Title
γ-Selective C(sp3)–H amination via controlled migratory hydroamination
Author(s)
Changseok Lee; Huiyeong Seo; Jinwon Jeon; Sungwoo Hong
Publication Date
2021-12-01
Journal
Nature Communications, v.12, no.1
Publisher
Nature Research
Abstract
© 2021, The Author(s).Remote functionalization of alkenes via chain walking has generally been limited to C(sp3)–H bonds α and β to polar-functional units, while γ-C(sp3)–H functionalization through controlled alkene transposition is a longstanding challenge. Herein, we describe NiH-catalyzed migratory formal hydroamination of alkenyl amides achieved via chelation-assisted control, whereby various amino groups are installed at the γ-position of aliphatic chains. By tuning olefin isomerization and migratory hydroamination through ligand and directing group optimization, γ-selective amination can be achieved via stabilization of a 6-membered nickellacycle by an 8-aminoquinoline directing group and subsequent interception by an aminating reagent. A range of amines can be installed at the γ-C(sp3)–H bond of unactivated alkenes with varying alkyl chain lengths, enabling late-stage access to value-added γ-aminated products. Moreover, by employing picolinamide-coupled alkene substrates, this approach is further extended to δ-selective amination. The chain-walking mechanism and pathway selectivity are investigated by experimental and computational methods.
URI
https://pr.ibs.re.kr/handle/8788114/10351
DOI
10.1038/s41467-021-25696-z
ISSN
2041-1723
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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