A simple and efficient copper-catalyzed procedure for the hydrosilylation of hindered and functionalized ketones

S Diez-Gonzalez; H Kaur; FK Zinn; ED Stevens; Steven Patrick Nolan

doi:10.1021/jo050397v

A simple and efficient copper-catalyzed procedure for the hydrosilylation of hindered and functionalized ketones

S Diez-Gonzalez, H Kaur, FK Zinn, ED Stevens, Steven Patrick Nolan

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

175 Citations (Scopus)

Abstract

The catalytic hydrosilylation of highly hindered and functionalized ketones is described. The combination of inexpensive catalyst precursors, CuCl and NHC-HX (NHC = N-heterocyclic carbene), leads to a highly efficient reduction mediator for the preparation of silyl ethers from unfunctionalized and functionalized alkyl, cyclic, bicyclic, aromatic, and heteroaromatic ketones. A series of catalyst precursors have been structurally characterized and a catalyst-structure activity relationship is discussed.

Original language	English
Pages (from-to)	4784-4796
Number of pages	13
Journal	The Journal of Organic Chemistry
Volume	70
Issue number	12
DOIs	https://doi.org/10.1021/jo050397v
Publication status	Published - 10 Jun 2005

Keywords

HETEROCYCLIC CARBENE COMPLEXES
ASYMMETRIC HYDROSILYLATION
ENANTIOSELECTIVE HYDROSILYLATION
CARBONYL-COMPOUNDS
ALPHA,BETA-UNSATURATED KETONES
HETEROAROMATIC KETONES
CONJUGATE REDUCTION
STABLE CARBENES
DIALKYL KETONES
ARYL KETONES

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title = "A simple and efficient copper-catalyzed procedure for the hydrosilylation of hindered and functionalized ketones",

abstract = "The catalytic hydrosilylation of highly hindered and functionalized ketones is described. The combination of inexpensive catalyst precursors, CuCl and NHC-HX (NHC = N-heterocyclic carbene), leads to a highly efficient reduction mediator for the preparation of silyl ethers from unfunctionalized and functionalized alkyl, cyclic, bicyclic, aromatic, and heteroaromatic ketones. A series of catalyst precursors have been structurally characterized and a catalyst-structure activity relationship is discussed.",

keywords = "HETEROCYCLIC CARBENE COMPLEXES, ASYMMETRIC HYDROSILYLATION, ENANTIOSELECTIVE HYDROSILYLATION, CARBONYL-COMPOUNDS, ALPHA,BETA-UNSATURATED KETONES, HETEROAROMATIC KETONES, CONJUGATE REDUCTION, STABLE CARBENES, DIALKYL KETONES, ARYL KETONES",

author = "S Diez-Gonzalez and H Kaur and FK Zinn and ED Stevens and Nolan, {Steven Patrick}",

year = "2005",

month = jun,

day = "10",

doi = "10.1021/jo050397v",

language = "English",

volume = "70",

pages = "4784--4796",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society (ACS)",

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TY - JOUR

T1 - A simple and efficient copper-catalyzed procedure for the hydrosilylation of hindered and functionalized ketones

AU - Diez-Gonzalez, S

AU - Kaur, H

AU - Zinn, FK

AU - Stevens, ED

AU - Nolan, Steven Patrick

PY - 2005/6/10

Y1 - 2005/6/10

N2 - The catalytic hydrosilylation of highly hindered and functionalized ketones is described. The combination of inexpensive catalyst precursors, CuCl and NHC-HX (NHC = N-heterocyclic carbene), leads to a highly efficient reduction mediator for the preparation of silyl ethers from unfunctionalized and functionalized alkyl, cyclic, bicyclic, aromatic, and heteroaromatic ketones. A series of catalyst precursors have been structurally characterized and a catalyst-structure activity relationship is discussed.

AB - The catalytic hydrosilylation of highly hindered and functionalized ketones is described. The combination of inexpensive catalyst precursors, CuCl and NHC-HX (NHC = N-heterocyclic carbene), leads to a highly efficient reduction mediator for the preparation of silyl ethers from unfunctionalized and functionalized alkyl, cyclic, bicyclic, aromatic, and heteroaromatic ketones. A series of catalyst precursors have been structurally characterized and a catalyst-structure activity relationship is discussed.

KW - HETEROCYCLIC CARBENE COMPLEXES

KW - ASYMMETRIC HYDROSILYLATION

KW - ENANTIOSELECTIVE HYDROSILYLATION

KW - CARBONYL-COMPOUNDS

KW - ALPHA,BETA-UNSATURATED KETONES

KW - HETEROAROMATIC KETONES

KW - CONJUGATE REDUCTION

KW - STABLE CARBENES

KW - DIALKYL KETONES

KW - ARYL KETONES

UR - http://www.scopus.com/inward/record.url?scp=20344396372&partnerID=8YFLogxK

U2 - 10.1021/jo050397v

DO - 10.1021/jo050397v

M3 - Article

SN - 0022-3263

VL - 70

SP - 4784

EP - 4796

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 12

ER -

A simple and efficient copper-catalyzed procedure for the hydrosilylation of hindered and functionalized ketones

Abstract

Keywords

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