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J Am Chem Soc. 2015 Apr 29;137(16):5536-41. doi: 10.1021/jacs.5b01916. Epub 2015 Apr 20.

Late-Stage Functionalization of 1,2-Dihydro-1,2-azaborines via Regioselective Iridium-Catalyzed C-H Borylation: The Development of a New N,N-Bidentate Ligand Scaffold.

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†Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States.
‡Department of Chemistry and Biochemistry, University of Oregon, Eugene, Oregon 97403-1253, United States.
§Department of Chemistry, The University of Alabama, Tuscaloosa, Alabama 35487-0036, United States.


The first general late-stage functionalization of monocyclic 1,2-azaborines at the C(6) position is described. Ir-catalyzed C-H borylation occurs regioselectively at the C(6) position of B-substituted 1,2-azaborines and is compatible with a range of substitution patterns at boron (e.g., hydride, alkoxide, alkyl, and aryl substituents). Subsequent Suzuki cross coupling with aryl- and heteroaryl bromides furnishes 1,2-azaborine-based biaryl compounds including 6-[pyrid-2-yl]-1,2-azaborines that represent novel κ(2)-N,N-bidentate ligands. The 6-[pyrid-2-yl]-B-Me-1,2-azaborine ligand has been demonstrated to form an emissive coordination complex with dimesitylboron that exhibits bathochromically shifted absorption and emission maxima and a higher photoluminescence quantum yield compared to its carbonaceous analogue.


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