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^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

29 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 - Jun 2011

User-Defined Keywords

asymmetric catalysis
copper
dipyridylphosphine ligands
hydrosilylation
ketones
polymethylhydrosiloxane

UN SDGs

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10.1002/adsc.201100105

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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.}",

note = "National Natural Science Foundation of China. Grant Number: 21032003, 20672026 New Century Excellent Talents in Chinese University Program. Grant Number: NCET-07-0250 Natural Science Foundation of Zhejiang Province. Grant Number: R406378, Y406193 Publisher copyright: {\textcopyright} 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2011",

month = jun,

doi = "10.1002/adsc.201100105",

language = "English",

volume = "353",

pages = "1457--1462",

journal = "Advanced Synthesis and Catalysis",

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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.

N1 - National Natural Science Foundation of China. Grant Number: 21032003, 20672026 New Century Excellent Talents in Chinese University Program. Grant Number: NCET-07-0250 Natural Science Foundation of Zhejiang Province. Grant Number: R406378, Y406193 Publisher copyright: © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2011/6

Y1 - 2011/6

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

UR - http://www.scopus.com/inward/record.url?scp=79959618441&partnerID=8YFLogxK

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

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