Alkoxide-Promoted Selective Hydroboration of N-Heteroarenes: Pivotal Roles of in situ Generated BH3 in the Dearomatization Process

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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-BH3 adducts undergo a hydride attack by alkoxyborohydrides, 2) in situ generated BH3 serves as a catalytic promoter, and 3) 1,4-dihydropyridyl borohydride is in a predominant resting state.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2019-05
Language
English
Article Type
Article
Citation

CHEMISTRY-A EUROPEAN JOURNAL, v.25, no.25, pp.6320 - 6325

ISSN
0947-6539
DOI
10.1002/chem.201901214
URI
http://hdl.handle.net/10203/263148
Appears in Collection
CH-Journal Papers(저널논문)
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