NHC-Catalyzed 1,2-Selective Hydroboration of Quinolines

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Selective dearomative transformation of readily available N-heteroarenes is a powerful tool accessing useful synthetic building units. Described herein is the NHC-catalyzed 1,2-selective hydroboration of quinolines with high functional group tolerance. Dihydroquinoline products could be isolated as their amide derivatives upon in situ N-protection, thus offering high synthetic utility of the current procedure. Combined experimental and computational studies revealed that the observed regioselectivity can be rationalized by proposing a six-membered transition state that collectively incorporates NHC catalyst, hydroborane reductant, and protonated quinoline substrate.
Publisher
AMER CHEMICAL SOC
Issue Date
2020-05
Language
English
Article Type
Article
Citation

ACS CATALYSIS, v.10, no.9, pp.5023 - 5029

ISSN
2155-5435
DOI
10.1021/acscatal.0c00884
URI
http://hdl.handle.net/10203/274317
Appears in Collection
CH-Journal Papers(저널논문)
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