Selective C�H bond functionlization of arenes continues to be an important avenue of research as a method to efficiently synthesize biologically relevant, substituted arenes. Conversion of unreactive C�H bonds to synthetically useful C�B bonds allows for production of more synthetically useful compounds.  In an effort to broaden the scope of arenes that could be selectively functionalized, substrate-directed C�H borylation reactions were pursued by replacing the commonly used di-tert-butylbipyridine and [Ir(COD)(OMe)]2 system with a ligand that leads to ortho-directed C�H borylation. 2-(aminomethyl)pyridine was revealed as an ideal ligand for the directed C�H borylation of benzylic amines, providing exclusive ortho-borylation with minimal bis-borylation. This talk will discuss the mechanism by which C�B bond formation occurs as well as the use of ortho-borylated benzylic amines as precursors in synthetic transformations. These valuable boronic esters have been used in further reactions, demonstrating their synthetic utility.

Substrate-directed <i>ortho</i>-C–H borylation of benzylic amines

243rd National Meeting (2012)

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Substrate-directed ortho-C–H borylation of benzylic amines