Synthetic utilization of Tetrafluoroethylene (cas 116-14-3)-containing silyl reagent (CH2=CHCF2CF2SiEt3) in Cu(I)-mediated cross-coupling reaction with various iodoarenes

Add time:08/25/2019    Source:sciencedirect.com

In this article, we revealed synthetic utilization of thermally stable as well as easy-handling triethyl (1,1,2,2-tetrafluorobut-3-en-1-yl)silane as the tetrafluoroethylenating agent through Cu(I)-mediated cross-coupling reaction with various iodoarenes, which would offer promising building block for versatile CF2CF2-containing organic molecules through easy carbon chain elongation at both ends. Specifically, the above tetrafluoroethylene-containing silyl reagent, readily prepared from commercially available 4-bromo-3,3,4,4-tetrafluorobut-1-ene, smoothly reacted with various iodoarenes in the presence of Cu(I), Ag(I), and pyridine in DMF at 60 °C for 16 h, the corresponding CF2CF2-containing aromatic compounds being afforded in moderate to good yields. Additionally, it was revealed that the coupling reaction dramatically facilitated when iodoarenes with an ortho-directing group, e.g., COOMe, were used as an electrophile, in which the acceleration effect was theoretically proved to stabilize the whole reaction system by coordination of the carbonyl oxygen to the copper atom.

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