Boron-Catalyzed Hydrogenative Reduction of Substituted Quinolines to Tetrahydroquinolines with Hydrosilanes

Narasimhulu Gandhamsetty; Sehoon Park; Sukbok Chang

doi:10.1055/s-0036-1588442

Boron-Catalyzed Hydrogenative Reduction of Substituted Quinolines to Tetrahydroquinolines with Hydrosilanes

Narasimhulu Gandhamsetty, Sehoon Park^*, Sukbok Chang

^*Corresponding author for this work

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

25 Scopus citations

Abstract

A metal-free procedure for the hydrogenative reduction of substituted N-heteroaromatics has been developed by using hydrosilanes as reducing agents. The optimized conditions were successfully applied to the reactions of quinolines, quinoxalines, and quinoline N -oxides. They were also effective for the reduction of quinolines bearing amino or hydroxy groups, where H ₂ was evolved through dehydrogenative silylation of the amine or hydroxy moieties. Preliminary mechanistic studies revealed that the initial step in the catalytic cycle involves 1,4-addition of the hydrosilane to the quinoline to give a 1,4-dihydroquinoline; this is followed by (transfer) hydrogenation to deliver the tetrahydroquinoline as the final product.

Original language	English
Pages (from-to)	2396-2400
Number of pages	5
Journal	Synlett
Volume	28
Issue number	18
DOIs	https://doi.org/10.1055/s-0036-1588442
State	Published - 13 Nov 2017
Externally published	Yes

Keywords

Lewis acids
boranes
hydrogenation
hydrosilanes
quinolines
quinoxalines

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10.1055/s-0036-1588442

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abstract = "A metal-free procedure for the hydrogenative reduction of substituted N-heteroaromatics has been developed by using hydrosilanes as reducing agents. The optimized conditions were successfully applied to the reactions of quinolines, quinoxalines, and quinoline N -oxides. They were also effective for the reduction of quinolines bearing amino or hydroxy groups, where H 2 was evolved through dehydrogenative silylation of the amine or hydroxy moieties. Preliminary mechanistic studies revealed that the initial step in the catalytic cycle involves 1,4-addition of the hydrosilane to the quinoline to give a 1,4-dihydroquinoline; this is followed by (transfer) hydrogenation to deliver the tetrahydroquinoline as the final product.",

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AU - Gandhamsetty, Narasimhulu

AU - Park, Sehoon

AU - Chang, Sukbok

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart.New York.

PY - 2017/11/13

Y1 - 2017/11/13

N2 - A metal-free procedure for the hydrogenative reduction of substituted N-heteroaromatics has been developed by using hydrosilanes as reducing agents. The optimized conditions were successfully applied to the reactions of quinolines, quinoxalines, and quinoline N -oxides. They were also effective for the reduction of quinolines bearing amino or hydroxy groups, where H 2 was evolved through dehydrogenative silylation of the amine or hydroxy moieties. Preliminary mechanistic studies revealed that the initial step in the catalytic cycle involves 1,4-addition of the hydrosilane to the quinoline to give a 1,4-dihydroquinoline; this is followed by (transfer) hydrogenation to deliver the tetrahydroquinoline as the final product.

AB - A metal-free procedure for the hydrogenative reduction of substituted N-heteroaromatics has been developed by using hydrosilanes as reducing agents. The optimized conditions were successfully applied to the reactions of quinolines, quinoxalines, and quinoline N -oxides. They were also effective for the reduction of quinolines bearing amino or hydroxy groups, where H 2 was evolved through dehydrogenative silylation of the amine or hydroxy moieties. Preliminary mechanistic studies revealed that the initial step in the catalytic cycle involves 1,4-addition of the hydrosilane to the quinoline to give a 1,4-dihydroquinoline; this is followed by (transfer) hydrogenation to deliver the tetrahydroquinoline as the final product.

KW - Lewis acids

KW - boranes

KW - hydrogenation

KW - hydrosilanes

KW - quinolines

KW - quinoxalines

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Boron-Catalyzed Hydrogenative Reduction of Substituted Quinolines to Tetrahydroquinolines with Hydrosilanes

Abstract

Keywords

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