Boron-catalyzed silylative reduction of quinolines: Selective sp3 C-Si bond formation

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Title
Boron-catalyzed silylative reduction of quinolines: Selective sp3 C-Si bond formation
Author(s)
Narasimhulu Grandhamsetty; Seewon Joung; Sung-Woo Park; Sehoon Park; Suk Bok Chang
Publication Date
2014-12
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.135, no.48, pp.16780 - 16783
Publisher
AMER CHEMICAL SOC
Abstract
A silylative reduction of quinolines to synthetically versatile tetrahydroquinoline molecules involving the formation of a C(sp3)−Si bond exclusively β to nitrogen is described. Triarylborane is a highly efficient catalyst (up to 1000 turnovers), and silanes serve as both a silyl source and a reducing reagent. The present procedure is convenient to perform even on a large scale with excellent stereoselectivity. Mechanistic studies revealed that the formation of a 1,4-addition adduct is rate-limiting while the subsequent C(sp3)−Si bond-forming step from the 1,4-adduct is facile.
URI
https://pr.ibs.re.kr/handle/8788114/1435
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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