We present a metal-free strategy to access fluoroalkyl-olefin linkages from fluoroalkane precursors and vinyl-pinacol boronic ester (BPin) reagents. This reaction sequence is templated by the boron reagent, which induces C-C bond formation upon oxidation. We developed this strategy into a one-pot synthetic protocol using RCFH precursors directly with vinyl-BPin reagents in the presence of a Brønsted base, which tolerated oxygen- and nitrogen-containing heterocycles, and aryl halogens. We also found that HCF (HCF-23; a byproduct of the Teflon industry) and CHF (HCF-32; a low-cost refrigerant) are amenable to this protocol, representing distinct strategies to generate RCFH and RCF molecules. Finally, we demonstrate that the vinyldifluoromethylene products can be readily derivatized, representing an avenue for late-stage modification after installing the fluoroalkyl unit.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10829021 | PMC |
| http://dx.doi.org/10.1039/d3sc05616c | DOI Listing |
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