Premium
Metal–free One–pot Synthesis of Functionalized Carbazoles
Author(s) -
Tao Sheng,
Wang RongJie,
Liu Ning,
Dai Bin
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700128
Subject(s) - carbazole , chemistry , halide , nucleophilic substitution , nucleophilic aromatic substitution , halogen , aryl , domino , selectivity , leaving group , aryl halide , nucleophile , polymer chemistry , organic chemistry , medicinal chemistry , catalysis , alkyl
A distinct dichotomy in product distribution was initially observed in metal‐free domino C−N and C−O bond forming reaction of carbazoles with aryl halides or benzyl halides. The fluoride group in halogenated fluorobenzenes almost exclusively undergoes double nucleophilic substitution with hydroxy group and amino group bearing carbazole ring. The reaction was found to occur preferentially at benzyl‐halogen atom when halobenzyl halides were present. Controlling experiments found that first coupling occurred with excellent site‐selectivity in favor of the hydroxy group on carbazole. A wide range of halogenated functionalized carbazoles, which have a wide utility for organic synthesis, polymer chemistry, and advanced functional materials application, were tolerated.