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B(C6F5)3‐Catalyzed Tandem Friedel‐Crafts and C−H/C−O Coupling Reactions of Dialkylanilines
Authors:Gaowen Zhai  Xueting Liu  Wentao Ma  Guoqiang Wang  Liu Yang  Shuhua Li  Youting Wu  Xingbang Hu
Abstract: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.
Keywords:Friedel-Crafts  C−  H/C−  O Coupling  B(C6F5)3  Lewis acid  Density functional calculation
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