Cross-Coupling of B-Benzyl-9-BBN with Aryl Halides and Triflates

Significance

Diarylmethane is an important structural unit in many compounds of interest for biological sciences. The herein described cross-coupling reaction of aryl halides with benzyl boranes serves as an easy synthetic approach for such structures. The process tolerates the majority of functional groups and is operationally simple. Substituents like hydroxyl, sulfonamide or aldehyde groups are easily tolerated. K₃PO₄ was found to be optimal as a base. In some cases, triphenylphosphine can be used as ligand for Pd, although the reaction usually requires highly active Pd-S-Phos catalyst (T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald J. Am. Chem. Soc. 2005, 127, 4685-4696).