An Efficient Organocatalyzed Interconversion of Silyl Ethers to Tosylates Using DBU and p-Toluenesulfonyl Fluoride
Vincent Gembus*, Francis Marsais, Vincent Levacher
*Laboratoire de Chimie Organique Fine et Hétérocyclique, UMR
6014, IRCOF, CNRS, Université et INSA de Rouen, B.P. 08, 76131 Mont-Saint-Aignan
Cédex, France, Email: vincent.gembus
insa-rouen.fr
V. Gembus, F. Marsais, V. Levacher, Synlett, 2008, 1463-1466.
DOI: 10.1055/s-2008-1078407
Abstract
A mild and efficient interconversion from silyl ethers to sulfonates esters proceeds readily in acetonitrile at room temperature in the presence of p-toluenesulfonyl fluoride and a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7ene (DBU). This method can be used with trimethysilyl (TMS), triethylsilyl (TES) and tert-butyldimethylsilyl (TBDMS) ethers.
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Key Words
organocatalysis, sulfonate esters, silyl ethers (TBDMS ethers), DBU, p-toluenesulfonyl fluoride
ID: J60-Y2008-1450
