Copper-dipyridylphosphine-polymethylhydrosiloxane: A practical and effective system for the asymmetric catalytic hydrosilylation of ketones

Xi Chang Zhang; Fei Fei Wu; Shijun Li; Ji Ning Zhou; Jing Wu; Ning Li; Wenjun Fang; Kim Hung Lam; Albert S.C. Chan

doi:10.1002/adsc.201100105

Copper-dipyridylphosphine-polymethylhydrosiloxane: A practical and effective system for the asymmetric catalytic hydrosilylation of ketones

Xi Chang Zhang, Fei Fei Wu, Shijun Li, Ji Ning Zhou, Jing Wu, Ning Li, Wenjun Fang, Kim Hung Lam, Albert S.C. Chan

Research output: Journal article publication › Journal article › Academic research › peer-review

26 Citations (Scopus)

Abstract

In the presence of the inexpensive and non-toxic stoichiometric reductant polymethylhydrosiloxane (PMHS), the chiral copper(II)-dipyridylphosphine catalyst displayed high efficiency in the stereoselective hydrosilylation of a wide scope of aryl alkyl and heteroaromatic ketones under an air atmosphere and mild conditions in good to excellent ees (up to 97%). With certain amounts of sodium tert-butoxide and tert-butyl alcohol as additives, the reaction on a 21-g substrate scale can be conveniently completed within a few hours even at a substrate-to-ligand (S/L) ratio of 50,000.

Original language	English
Pages (from-to)	1457-1462
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	353
Issue number	9
DOIs	https://doi.org/10.1002/adsc.201100105
Publication status	Published - 1 Jun 2011

Keywords

asymmetric catalysis
copper
dipyridylphosphine ligands
hydrosilylation
ketones
polymethylhydrosiloxane

ASJC Scopus subject areas

Catalysis
Organic Chemistry

More information

10.1002/adsc.201100105

Cite this

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title = "Copper-dipyridylphosphine-polymethylhydrosiloxane: A practical and effective system for the asymmetric catalytic hydrosilylation of ketones",

abstract = "In the presence of the inexpensive and non-toxic stoichiometric reductant polymethylhydrosiloxane (PMHS), the chiral copper(II)-dipyridylphosphine catalyst displayed high efficiency in the stereoselective hydrosilylation of a wide scope of aryl alkyl and heteroaromatic ketones under an air atmosphere and mild conditions in good to excellent ees (up to 97%). With certain amounts of sodium tert-butoxide and tert-butyl alcohol as additives, the reaction on a 21-g substrate scale can be conveniently completed within a few hours even at a substrate-to-ligand (S/L) ratio of 50,000.",

keywords = "asymmetric catalysis, copper, dipyridylphosphine ligands, hydrosilylation, ketones, polymethylhydrosiloxane",

author = "Zhang, {Xi Chang} and Wu, {Fei Fei} and Shijun Li and Zhou, {Ji Ning} and Jing Wu and Ning Li and Wenjun Fang and Lam, {Kim Hung} and Chan, {Albert S.C.}",

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language = "English",

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journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

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Copper-dipyridylphosphine-polymethylhydrosiloxane: A practical and effective system for the asymmetric catalytic hydrosilylation of ketones. / Zhang, Xi Chang; Wu, Fei Fei; Li, Shijun et al.
In: Advanced Synthesis and Catalysis, Vol. 353, No. 9, 01.06.2011, p. 1457-1462.

Research output: Journal article publication › Journal article › Academic research › peer-review

TY - JOUR

T1 - Copper-dipyridylphosphine-polymethylhydrosiloxane

T2 - A practical and effective system for the asymmetric catalytic hydrosilylation of ketones

AU - Zhang, Xi Chang

AU - Wu, Fei Fei

AU - Li, Shijun

AU - Zhou, Ji Ning

AU - Wu, Jing

AU - Li, Ning

AU - Fang, Wenjun

AU - Lam, Kim Hung

AU - Chan, Albert S.C.

PY - 2011/6/1

Y1 - 2011/6/1

N2 - In the presence of the inexpensive and non-toxic stoichiometric reductant polymethylhydrosiloxane (PMHS), the chiral copper(II)-dipyridylphosphine catalyst displayed high efficiency in the stereoselective hydrosilylation of a wide scope of aryl alkyl and heteroaromatic ketones under an air atmosphere and mild conditions in good to excellent ees (up to 97%). With certain amounts of sodium tert-butoxide and tert-butyl alcohol as additives, the reaction on a 21-g substrate scale can be conveniently completed within a few hours even at a substrate-to-ligand (S/L) ratio of 50,000.

AB - In the presence of the inexpensive and non-toxic stoichiometric reductant polymethylhydrosiloxane (PMHS), the chiral copper(II)-dipyridylphosphine catalyst displayed high efficiency in the stereoselective hydrosilylation of a wide scope of aryl alkyl and heteroaromatic ketones under an air atmosphere and mild conditions in good to excellent ees (up to 97%). With certain amounts of sodium tert-butoxide and tert-butyl alcohol as additives, the reaction on a 21-g substrate scale can be conveniently completed within a few hours even at a substrate-to-ligand (S/L) ratio of 50,000.

KW - asymmetric catalysis

KW - copper

KW - dipyridylphosphine ligands

KW - hydrosilylation

KW - ketones

KW - polymethylhydrosiloxane

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U2 - 10.1002/adsc.201100105

DO - 10.1002/adsc.201100105

M3 - Journal article

AN - SCOPUS:79959618441

SN - 1615-4150

VL - 353

SP - 1457

EP - 1462

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 9

ER -

Copper-dipyridylphosphine-polymethylhydrosiloxane: A practical and effective system for the asymmetric catalytic hydrosilylation of ketones

Abstract

Keywords

ASJC Scopus subject areas

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