Efficient and Facile Ar−Si Bond Cleavage by Montmorillonite KSF:  Synthetic and Mechanistic Aspects of Solvent-Free Protodesilylation Studied by Solution and Solid-State MAS NMR

Yossi Zafrani,* Eytan Gershonov, and Ishay Columbus
Department of Organic Chemistry, Israel Institute for Biological Research, Ness-Ziona 74100, Israel yossiz@iibr.gov.il
J. Org. Chem., 2007, 72 (18), pp 7014–7017
DOI: 10.1021/jo0706170
Publication Date (Web): August 4, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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A facile and efficient method for the cleavage of the Ar−Si bond of various aryl trimethyl silanes is described. When adsorbed on montmorillonite KSF (mont KSF), these arylsilanes readily undergo a solvent-free protodesilylation to the corresponding arenes at room temperature in excellent yields. This approach seems to be superior to the traditional mild methods (i.e., desilylation by TFA, TBAF, CsF), in terms of reaction yield, rate, and environmentally benign conditions. Some mechanistic studies using both solution and solid-state magic-angle spinning (SS MAS) 1H NMR are also presented.

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History

  • Published In Issue August 31, 2007
  • Received April 1, 2007

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