Dasgupta Ayan, Stefkova Katarína, Babaahmadi Rasool, Gierlichs Lukas, Ariafard Alireza, Melen Rebecca L
Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, Cymru/Wales, UK.
School of Natural Sciences - Chemistry, University of Tasmania, Private Bag 75, Hobart, Tasmania, 7001, Australia.
Angew Chem Int Ed Engl. 2020 Sep 1;59(36):15492-15496. doi: 10.1002/anie.202007176. Epub 2020 Jul 15.
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 were used to elucidate the mechanism for this alkenylation reaction.
在此，我们报道了一种简便、温和的反应方案，可在无过渡金属催化剂的情况下形成碳-碳键。我们展示了芳基酯与α-重氮酯的无金属烯基化反应，以得到高度官能化的烯炔产物。使用催化量的三（五氟苯基）硼烷（10 - 20 mol%），以良好至优异的产率（36 - 87%）得到C = C偶联产物（31个实例）。采用密度泛函理论（DFT）研究来阐明这种烯基化反应的机理。
