Rhodium-Catalyzed Oxidative Olefination of N-(2-(4,5-Dihydrooxazol-2-yl)phenyl)amides with Arylethenes via Extraordinary N-Aryl C-H Bond Functionalization

Typical procedure for N-aryl oxidative olefination of amide tethered aryl oxazolineAn oven-dried Schlenk tube was charged with N-(2-(4,5-dihydrooxazol-2-yl)phenyl)amides 1 (0.1 mmol), arylethenes 2 (2.0 equiv), [RhCp*Cl2]2 (3 mol%), Cu(OAc)2 (2.0 equiv), AgBF4 (0.1 equiv) , then DCE (1 mL) was added to the reaction system.The reaction was stirred at 70 o C under air for 10 h (TLC monirored).Upon completion of the reaction, cooling to room temperature, the reaction mixture diluted with ethyl acetate and washed with saturated brine.The combined organic phase was dried over anhydrous Na2SO4.After the solvent was evaporated in vacuo, the residues were purified by column chromatography, eluting with PET (petroleum ether)/ EtOAc to afford the desired 3.