Improved Synthesis of Aryltrialkoxysilanes via Treatment of Aryl Grignard or Lithium Reagents with Tetraalkyl Orthosilicates

Amy S. Manoso, Chuljin Ahn, Arash Soheili, Christopher J. Handy, Reuben Correia, W. Michael Seganish and Philip DeShong*

*Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, Email: deshongumd.edu

A. S. Manoso, C. Ahn, A. Soheili, C. J. Handy, R. Correia, W. Seganish, P. DeShong, J. Org. Chem., 2004, 69, 8305-8314.

DOI: 10.1021/jo048667h

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Abstract

General reaction conditions for the synthesis of aryl(trialkoxy)silanes from aryl Grignard and lithium reagents and tetraalkyl orthosilicates (Si(OR)₄) have been developed. Ortho-, meta-, and para-substituted bromoarenes underwent efficient metalation and silylation at low temperature to provide aryl siloxanes.

see article for more example

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Improved Synthesis of Aryltriethoxysilanes via Palladium(0)-Catalyzed Silylation of Aryl Iodides and Bromides with Triethoxysilane

R. Correia, P. DeShong, J. Org. Chem., 2001, 66, 7449-7455.

Palladium-Catalyzed Arylation of Allylic Benzoates Using Hypervalent Siloxane Derivatives

R. Correia, P. DeShong, J. Org. Chem., 2001, 66, 7159-7165.

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Key Words

Arylsiloxanes

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ID: J42-Y2004-2470