A qualitative examination of the effects of silicon substituents on the efficiency of cross-coupling reactions.

A qualitative examination of the effects of silicon substituents on the efficiency of cross-coupling reactions. Research Abstract Details 

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A qualitative examination of the effects of silicon substituents on the efficiency of cross-coupling reactions. Abstract Text:

Scott E Denmark,Luc Neuville,Matthew E L Christy,Steven A Tymonko,

A qualitative study of the effects of various substituents on the silicon atom in cross-coupling reactions of alkenylsilanes has been carried out. In intermolecular competition experiments, the influence of carbon-based groups (methyl, ethyl, isopropyl, tert-butyl, phenyl, and 3,3,3-trifluoropropyl) and alkoxy groups (monoethoxydimethyl-, diethoxymethyl-, and triethoxy) on the silicon have been evaluated under activation by two different methods, fluoride (TBAF) and silanolate (TMSOK). The influence of the substituents was highly dependent on the method of activation. In the presence of TBAF, there was only a modest steric effect (except for tert-butyl substituents), and the efficiency decreased slightly with increasing numbers of alkoxy groups. In the presence of TMSOK, a significant steric effect was noted, but the number of alkoxy groups had almost no influence. These trends were interpreted in terms of the divergent mechanisms for the cross-coupling process.

A qualitative examination of the effects of silicon substituents on the efficiency of cross-coupling reactions. Publishing Authors By Initials

SE Denmark,L Neuville,ME Christy,SA Tymonko,

For similar inorganic chemicals: silicon compounds: silanes research abstracts see: inorganic chemicals: silicon compounds: silanes research

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A qualitative examination of the effects of silicon substituents on the efficiency of cross-coupling reactions. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: The Journal of organic chemistry

VOLUME: 71

Page Numbers: 8500-9

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 27

MONTH: Oct

YEAR: 2006

A qualitative examination of the effects of silicon substituents on the efficiency of cross-coupling reactions. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 2985193

A qualitative examination of the effects of silicon substituents on the efficiency of cross-coupling reactions. Keywords Mesh Terms:

KEYWORDS: Silanes

MESH TERMS: chemistry

Chemical & Substance for Abstract: A qualitative examination of the effects of silicon substituents on the efficiency of cross-coupling reactions. Information

Substance Name: Silanes

Registry Number: 0

Grant and Affiliation Information for A qualitative examination of the effects of silicon substituents on the efficiency of cross-coupling reactions.

AFFILIATION: Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu

Country: United States

AGENCY: United States NIGMS

GRANT: GM63167

ACRONYM: GM

MEDLINETA: J Org Chem

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