Copper-Catalyzed Diarylation of Activated Alkenes with Diaryliodonium Salts

Abstract

Cu(OTf)₂-catalyzed diarylation of activated alkenes by using diaryliodonium(III) salts has been developed. With this method, arylated oxindoles can be easily accessed in good yields. Insights into the mechanism of copper-catalyzed arylations are discussed, and the findings are expected to help increase the level of understanding of catalytic arylations with diaryliodonium salts.

Key words

alkene activation - arylation - diaryliodonium salts - oxindoles - copper triflate

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• 14 Cascade Reaction of N-Arylacrylamide with Diaryliodonium Salts; General Procedure: Cu(OTf)₂ (0.05 mmol, 0.1 equiv), N-arylacrylamide (0.5 mmol, 1.0 equiv) and diphenyliodonium salt (1.0 mmol, 2.0 equiv) were added to a dried Schlenk tube. The tube was degassed with nitrogen three times, then DCE (2.0 mL) was added by using a syringe. The mixture was heated and stirred at 130 °C for 16 h, then cooled to r.t. and the solvent was evaporated in vacuum. The crude products were directly purified by flash column chromatography on silica gel (petroleum ether–EtOAc, 10:1) to afford the desired oxindole.