Herein we report a facile, mild reaction protocol to form carbon-carbon bonds in the absence of transition metal catalysts. We demonstrate the metal-free alkenylation reactions of aryl esters with α-diazoesters to give highly functionalized enyne products. Catalytic amounts of tris(pentafluorophenyl)borane (10–20 mol%) are employed to afford the C=C coupled products (31 examples) in good to excellent yields (36–87%). DFT studies have been undertaken to elucidate the mechanism for this alkenylation reaction.
Data includes experimental procedures, raw NMR and X-ray data.
Research results based upon these data are published at http://doi.org/10.1002/anie.202007176
Funding
Expanding the Boundaries in Main Group Chemistry: New Boranes for Novel Reactivity
Engineering and Physical Sciences Research Council