Triarylborane‐Catalyzed Alkenylation Reactions of Aryl Esters with Diazo Compounds
Ayan Dasgupta, Katarína Stefkova, Rasool Babaahmadi, Lukas Gierlichs, Alireza Ariafard, Rebecca L. Melen
Abstract
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.
Topics & Concepts
DiazoChemistryCatalysisBoraneArylCombinatorial chemistryEnyneMedicinal chemistryTrisMetalOrganic chemistryAlkylBiochemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions