Copper‐Mediated Diamination of Arylboronic Acids for the Synthesis of 2‐Aryl Benzimidazoles Using Trimethylsilyl Azide as the Amino Sources with Aldehydes
Zeqiang Xie, Fengtao Zhou, Ke Ding
Abstract
Abstract 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. magnified image
Topics & Concepts
ChemistryTrimethylsilyl azideAzideArylCopperCycloadditionAminationTandemTrimethylsilylOrganic chemistryCombinatorial chemistryCurtius rearrangementCatalysisComposite materialMaterials scienceAlkylCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques