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B(C 6 F 5 ) 3 ‐Catalyzed Tandem Friedel‐Crafts and C−H/C−O Coupling Reactions of Dialkylanilines
Author(s) -
Zhai Gaowen,
Liu Xueting,
Ma Wentao,
Wang Guoqiang,
Yang Liu,
Li Shuhua,
Wu Youting,
Hu Xingbang
Publication year - 2020
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202000763
Subject(s) - friedel–crafts reaction , tandem , catalysis , coupling (piping) , chemistry , medicinal chemistry , materials science , organic chemistry , composite material
Abstract Tandem Friedel‐Crafts (FC) and C−H/C−O coupling reactions catalyzed by tris(pentafluorophenyl) borane (B(C 6 F 5 ) 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(C 6 F 5 ) 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.