Preparation and synthetic applications of aryl tetraflates (ArOSO2CF2CF2H) |
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Authors: | Rostovtsev Vsevolod V Bryman Lois M Junk Christopher P Harmer Mark A Carcani Liane G |
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Institution: | DuPont Central Research and Development, Experimental Station, Wilmington, Delaware 19880, USA. vsevolod.rostovtsev@usa.dupont.com |
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Abstract: | We have recently developed an improved synthetic route to 1,1,2,2-tetrafluoroethanesulfonic acid (HCF2CF2SO3H, TFESA) and explored the applications of this newly available superacid in catalysis. Low volatility, ease of handling, 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 sulfonates. We prepared several aryl esters of 1,1,2,2-tetrafluoroethanesulfonic acid (aryl tetraflates) and showed that they can be used in a number of palladium-catalyzed coupling reactions (Suzuki, Heck, and Buchwald-Hartwig couplings). While the reactivity of tetraflates lies between that of triflates and chlorides, tetraflates appear to be more thermally stable. Additionally, the presence of a hydrogen atom in the tetraflate group facilitates monitoring of reactions and characterization of derivatives. |
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