Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 15, Pages 4916-4919Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b03147
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Funding
- Shanghai Science and Technology Committee [13QA1400500]
- Shanghai Leading Academic Discipline Project [B108]
- National Nature Science Foundation of China [21102018, 21273042, 21372048]
- National Basic Research Program of China [2011CB808505]
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A bulky organoborane (Ar2BMe)-B-F (Ar-F = 2,4,6-tris(trifluoromethyl)phenyl, 1) has been synthesized. In C6D6 solution this organoborane and pyridine form a frustrated Lewis pair. Under mild conditions, 1 can efficiently catalyze 1,4-hydroboration of a series of pyridines. This reaction is highly chemo- and regioselective. The reaction intermediate, a boronium complex [Py(2)Bpin][(Ar2B)-B-F(H)Me] (3), was characterized in solution by NMR spectroscopy, which was also confirmed by DFT calculation.
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