4 years ago

Enantioselective Borylation of Aromatic C−H Bonds with Chiral Dinitrogen Ligands

Enantioselective Borylation of Aromatic C−H Bonds with Chiral Dinitrogen Ligands
Bo Su, Zhang-Jie Shi, Tai-Gang Zhou, John F. Hartwig, Pei-Lin Xu
The borylation of C−H bonds catalyzed by transition metals has been investigated extensively in the past two decades, but no iridium-catalyzed enantioselective borylation of C−H bonds has been reported. We report a set of iridium-catalyzed enantioselective borylations of aromatic C−H bonds. This reaction relies on a set of newly developed chiral quinolinyl oxazoline ligands. This process proceeds under mild conditions with good to excellent enantioselectivity, and the borylated products can be converted to enantioenriched derivatives containing new C−O, C−C, C−Cl, or C−Br bonds. Enantioselective C−H borylation: The first Ir-catalyzed enantioselective borylation of aromatic C−H bonds was developed with up to 98:2 er. The success of this reaction relies on a newly developed catalyst that derives from an iridium precursor and a chiral quinolinyl oxazoline ligand.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201702628

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