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Trimethylsilyl fluorosulfonyldifluoroacetate (TFDA): a new, highly efficient difluorocarbene reagent |
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| Authors: | William R Dolbier Jr Feng Tian An-Rong Li Olivia Bautista J Marshall Baker Pauline Anselme Aneta Modzelewska Merle A Battiste |
| Institution: | a Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611-7200, USA b Chemistry Department, Adam Mickiewicz University, Poznan, Poland c Shanghai Institute of Organic Chemistry, 354 Fenglin Lu, Shanghai 200032, China |
| Abstract: | TFDA is readily prepared from the reaction of fluorosulfonyldifluoroacetic acid with trimethylsilyl chloride, and it is a very effective and efficient source of difluorocarbene for use in addition reactions to alkenes of a broad scope of reactivities. Acid-sensitive substrates may require an additional purification step involving treatment of the distilled TFDA with sufficient Et3N to remove the acid impurity. Other trialkylsilyl fluorosulfonyldifluoroacetates can also be prepared, and they have been found to have reactivities similar to TFDA. The triethyl derivative, TEFDA is more convenient to prepare in a pure state and has similar reactivity to TFDA. Thus, it may prove to be a superior reagent. |
| Keywords: | Trimethylsilyl fluorosulfonyldifluoroacetate Difluorocarbene reagent Addition reactions |
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