Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 16, Pages 5536-5541Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b01916
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Funding
- National Science Foundation [CHE-1361618]
- U.S. Army [RM097E-A, W909MY-10-C-0073]
- Robert Ramsay Chair Fund of The University of Alabama
- LaMattina Family Graduate Fellowship
- Camille Dreyfus Teacher-Scholar Awards Program for a Teacher-Scholar award
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1361618] Funding Source: National Science Foundation
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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 kappa(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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