Affiliation:
1. Departament de Química Analítica i Química Orgànica Universitat Rovira i Virgili C/Marcel ⋅ lí Domingo 1 43007 Tarragona Spain
2. Department of Chemistry and Biomolecular Sciences and Centre for Catalysis Research and Innovation University of Ottawa 30 Marie Curie Ottawa ON K1N 6N5 Canada
Abstract
AbstractIn this study, we have developed a metal‐mediated synthetic method for incorporating the 1,1,2,2‐tetrafluoroethyl (CF2CF2H) motif into unactivated, electron‐rich alkenyl iodides using cross‐coupling reactions. We discovered that the stable Cu(CF2CF2H)(PPh2Me)3 complex, while unreactive with these substrates, serves as a P‐ligated reservoir for the formation of solvent‐stabilized “ligandless” and reactive CuCF2CF2H species. This transformation occurs upon addition of CuBr, which partially scavenges the P‐ligand in the form of CuBr(PPh2Me)3. The resulting in situ generated solvent stabilized “ligandless” system significantly enhances the reactivity of the complex, particularly towards challenging electron‐rich substrates. This advancement enables the synthesis of HCF2CF2‐glycals, as well as nucleosides/nucleobases and arenes.
Funder
Florida Polytechnic University
Universitat Rovira i Virgili
Natural Sciences and Engineering Research Council of Canada
Cited by
1 articles.
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