A mild, efficient and highly chemoselective alkylation of thiols using Cs2CO3 and TBAI

ORGN 617

Robert A. Smith1, Adam K. Nischwitz1, Terrence E. Gavin2, and Ralph Nicholas Salvatore1. (1) Department of Chemistry, Western Kentucky University, 1 Big Red Way, Bowling Green, KY 42101-3576, (2) Department of Chemistry, Iona College, 715 North Avenue, New Rochelle, NY 10801
Thiols are a fundamental and important functional group in organic chemistry, and the literature contains ample reports of organic, bioorganic and medicinal chemistry on this group. Consequently, numerous synthetic methods have been developed. One general protocol is the condensation of activated alkyl halides with alkali metal thiolates. However, the synthetic scope of this classical reaction is limited by its long reaction time, high reaction temperature, and low yield. Therefore, we have set out to investigate milder reaction conditions.

A convenient one-pot synthetic method for the formation of dialkyl sulfides and alkyl aryl sulfides employing various alkyl halides and thiols using cesium carbonate, tetrabutylammonium iodide (TBAI) and DMF is reported. In particular, this method is mild, efficient and highly chemoselective, which circumvents many of the chronic problems encountered in previous reports that will offer a general synthetic procedure for construction of the C-S bond.

 

New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004