B(C6F5)3‐Catalyzed Tandem Friedel‐Crafts and C−H/C−O Coupling Reactions of Dialkylanilines.

Tandem Friedel‐Crafts (FC) and C−H/C−O coupling reactions catalyzed by tris(pentafluorophenyl) borane (B(C6F5)3) were achieved without using any other additive in the absence of solvent. This process can be used for the reactions between a series of dialkylanilines and vinyl ethers with good isolated yields of bis(4‐dialkylaminophenyl) compounds. Based on combined theoretical and experimental studies, the possible reaction mechanism was proposed. B(C6F5)3 can activate the C=C and C−O bond for FC and C−H/C−O coupling reactions respectively. The FC reaction is slow, which is followed by a fast C−H/C−O coupling. [ABSTRACT FROM AUTHOR]