Further insight into aromatic borylation chemistry

UK scientists have investigated the interaction between borane Lewis acids and arenes through the synthesis of a dibromoborenium cation.

Thorough characterisation of arene–borane Lewis acid contacts is essential for understanding the mechanistic pathway for aromatic borylation chemistry and by extension, electrophilic aromatic substitution. However, until now, structural determination of such arene–borane compounds has been somewhat ambiguous.

Simon Aldridge and his team have set out to fill this knowledge gap by reacting a sterically encumbered pyridine donor with BBr3 to yield a cationic tri-coordinate borane–arene complex. Employing crystallography and computational studies, the team found that a weak electrostatic interaction is responsible for the short contacts between the positively charged boron centre and the arene π system.

Read the ChemComm article to find out more…

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