Although the carbon chain homologation reaction has been well developed in general organic chemistry, the analogous fluoroalkyl chain homologation reaction is rare. In this presentation, we will describe our recent work on the efficient pentafluoroethylation with a widely-used trifluoromethylating agent--TMSCF3. We used two strategies to achieve C1 to C2 carbon chain elongation: 1) the conversion of TMSCF3 to tetrafluoroethylene (TFE), followed by the use of TFE as a C2 synthon, and 2) the conversion of TMSCF3 to CuCF3, followed by the spontaneous conversion of CuCF3 to CuC2F5 for pentafluoroethylation. The in situ-formed CF2=CF2 and CuC2F5 can be used in various pentafluoroethylation or tetrafluoroethylation with high efficacy.

From C1 to C2: Pentafluoroethylation with Ruppert-Prakash reagent

2019 Spring National Meeting

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