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Copper‐Mediated Diamination of Arylboronic Acids for the Synthesis of 2‐Aryl Benzimidazoles Using Trimethylsilyl Azide as the Amino Sources with Aldehydes
Author(s) -
Xie Zeqiang,
Zhou Fengtao,
Ding Ke
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000385
Subject(s) - chemistry , trimethylsilyl azide , azide , aryl , copper , cycloaddition , amination , tandem , trimethylsilyl , organic chemistry , combinatorial chemistry , curtius rearrangement , catalysis , alkyl , materials science , composite material
A direct and versatile copper‐mediated three‐component reaction of arylboronic acids, trimethylsilyl azide and aldehydes for the synthesis of benzimidazoles is reported. The reaction is well tolerated by a wide range of substituted aromatic aldehydes and aromatic boronic acids to produce the corresponding benzimidazoles in moderate to high yields. Mechanism investigations demonstrated that copper‐promoted Chan‐Evans‐Lam coupling, C−H amination, and oxidative cycloaddition are involved in the tandem processes.