Palladium-catalyzed chemoselective Suzuki-Miyaura cross-coupling reaction of poly(pseudo)halogenated arenes

This paper presents general examples of the palladium-catalyzed chemoselective Suzuki-Miyaura cross-coupling reaction of polyhalogenated aryl triflates with a reactivity order of C-Br > C-Cl > C-OTf. A diverse array of bromo(hetero)aryl triflates was successfully coupled with (hetero)aryl boronic acids, achieving excellent reactivity and chemoselectivity. This was accomplished using a catalyst system composed of Pd(OAc)2 and SelectPhos (L1), with catalyst loadings reducible to as low as 0.02 mol% Pd. The sequential double functionalization of bromochloroaryl triflates was also demonstrated successfully, paving the way for the synthesis of terphenyl derivatives.