Synthetic applications of 1,1,2,2-tetrafluoroethanesulfonic acid and its derivatives: An attractive alternative to triflic acid

ORGN 411

Vsevolod V. Rostovtsev, vsevolod.rostovtsev@usa.dupont.com, DuPont CR&D, Experimental Station, PO Box 80328, Wilmington, DE 19880-0328, Mark A. Harmer, Mark.A.Harmer@usa.dupont.com, Experimental Station, Dupont, Wilmington, DE 19880-0356, and Christopher Junk, DuPont Central Research and Development, DuPont CR&D, Experimental Station, PO Box 80328, Wilmington, DE 19880-0328.
We have recently developed an improved synthetic route to 1,1,2,2-tetrafluoroethanesulfonic acid (HCF2CF2SO3H or TFESA) and explored the applications of this newly available superacid in catalysis. Low volatility and a convenient 1H NMR handle make this acid an attractive alternative to triflic acid. TFESA can also be converted to several of its derivatives: anhydride, sulfonyl chloride and sulfonyl fluoride, which provide a good entry point for the synthesis of aryl and vinyl sulfonates. We prepared a variety of sulfonates and demonstrated their utility in metal-catalyzed cross-coupling reactions.
 

New Reactions and Methodology
1:00 PM-5:20 PM, Tuesday, 12 September 2006 Moscone Center -- Room 133, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006