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 value-added fine chemicals. In an effort to broaden the scope of arenes that could be selectively functionalized, iridium-catalyzed substrate-directed arene C�H borylation reactions were pursued by replacing the commonly used di-tert-butylbipyridine ligand with a hemi-labile bidentate ligand. 2-Picolyamine was revealed as an ideal ligand for the directed C�H borylation of benzylic amines, providing exclusive ortho-borylation with minimal bis-borylation. Further ligand screening has demonstrated a significant effect on borylation selectivity and provides preliminary insights into mechanistic considerations. These ligand effects have been used to expand the scope of directing groups that can be used to obtain ortho-borylation. Preliminary applications of these valuable boronate esters in synthetic reactions will also be discussed.

Substrate-directed ortho C-H borylation of substituted arenes

246th National Meeting (2013)

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