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Jeonghyo, Lee
분자활성 촉매반응 연구단
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Cobalt-Catalyzed Intermolecular C-H Amidation of Unactivated Alkanes

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Title
Cobalt-Catalyzed Intermolecular C-H Amidation of Unactivated Alkanes
Author(s)
Jeonghyo Lee; Seongho Jin; Dongwook Kim; Soon Hyeok Hong; Sukbok Chang
Publication Date
2021-04
Journal
Journal of the American Chemical Society, v.143, no.13, pp.5191 - 5200
Publisher
NLM (Medline)
Abstract
Alkanes are an abundant and inexpensive source of hydrocarbons; thus, development of new methods to convert the hydrocarbon feedstocks to value-added chemicals is of high interest. However, it is challenging to achieve such transformation in a direct and selective manner mainly due to the intrinsic inertness of their C-H bonds. We herein report a tailored Cp*Co(III)(LX)-catalyzed efficient and site-selective intermolecular amidation of unactivated hydrocarbons including light alkanes. Electronic modulation of the cobalt complexes led to the enhanced amidation efficiency, and these effects were theoretically rationalized by the FMO analysis of presupposed cobalt nitrenoid species. Under the current cobalt protocol, a secondary C-H bond selectivity was observed in various nonactivated alkanes to reverse the intrinsic tertiary preference, which is attributed to the steric demands of the cobalt system that imposes difficulties in accessing tertiary C-H bonds. Experimental and computational studies suggested that the putative triplet Co nitrenoids are transferred to the C-H bonds of alkanes via a radical-like hydrogen abstraction pathway.
URI
https://pr.ibs.re.kr/handle/8788114/9729
DOI
10.1021/jacs.1c01524
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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