Alkoxide-Promoted Selective Hydroboration of N-Heteroarenes: Pivotal Roles of in situ Generated BH 3 in the Dearomatization Process

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Title
Alkoxide-Promoted Selective Hydroboration of N-Heteroarenes: Pivotal Roles of in situ Generated BH 3 in the Dearomatization Process
Author(s)
Eunchan Jeong; Joon Heo; Sehoon Park; Sukbok Chang
Publication Date
2019-05
Journal
CHEMISTRY-A EUROPEAN JOURNAL, v.25, no.25, pp.6320 - 6325
Publisher
WILEY-V C H VERLAG GMBH
Abstract
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim While numerous organo(metallic)catalyst systems were documented for dearomative hydroboration of N-aromatics, alkoxide base catalysts have not been disclosed thus far. Described herein is the first example of alkoxide-catalyzed hydroboration of N-heteroaromatics including pyridines, providing a broad range of reduced N-heterocycles with high efficiency and selectivity. Mechanistic studies revealed an unprecedented counterintuitive dearomatization pathway, in which 1) pyridine-BH 3 adducts undergo a hydride attack by alkoxyborohydrides, 2) in situ generated BH 3 serves as a catalytic promoter, and 3) 1,4-dihydropyridyl borohydride is in a predominant resting state ⓒ 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinh
URI
https://pr.ibs.re.kr/handle/8788114/5973
ISSN
0947-6539
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
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