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

Narasimhulu Gandhamsetty; Seewon Joung; Sung Woo Park; Sehoon Park; Sukbok Chang

doi:10.1021/ja510674u

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

Narasimhulu Gandhamsetty, Seewon Joung, Sung Woo Park, Sehoon Park^*, Sukbok Chang

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

105 Scopus citations

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.

Original language	English
Pages (from-to)	16780-16783
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	48
DOIs	https://doi.org/10.1021/ja510674u
State	Published - 3 Dec 2014
Externally published	Yes

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title = "Boron-catalyzed silylative reduction of quinolines: Selective sp3 C-Si bond formation",

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.",

author = "Narasimhulu Gandhamsetty and Seewon Joung and Park, {Sung Woo} and Sehoon Park and Sukbok Chang",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

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T1 - Boron-catalyzed silylative reduction of quinolines

T2 - Selective sp3 C-Si bond formation

AU - Gandhamsetty, Narasimhulu

AU - Joung, Seewon

AU - Park, Sung Woo

AU - Park, Sehoon

AU - Chang, Sukbok

PY - 2014/12/3

Y1 - 2014/12/3

N2 - 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.

AB - 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.

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M3 - 文章

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SN - 0002-7863

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SP - 16780

EP - 16783

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 48

ER -

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

Abstract

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