Attempted halogenation of ambiphilic 1,2,3-benzodiazaborines: Balancing Lewis acidity and Lewis basicity

Key Points

• The aim is to explore how the Lewis basicity of 1,2,3-diazaborines affects their halogenation reactions.
• Investigated the conversion of B–OH groups to B–Hal groups using BX3.
• Analyzed competitive ortho-directed C−H borylation during the reaction process.
• Utilized synthetic techniques to assess reactivity of various compounds.
• Demonstrated that competitive reactions hinder direct halogenation.
• Identified specific conditions under which halogenation could occur.
• Showed that the Lewis acidity of BX3 significantly influences the reaction outcome.