Organoborane
Catalyzed Regioselective 1,4-Hydroboration
of Pyridines
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Abstract
A bulky organoborane
Ar<sup>F</sup><sub>2</sub>BMe (Ar<sup>F</sup> = 2,4,6-tris(trifluoromethyl)phenyl, <b>1</b>) has been synthesized.
In C<sub>6</sub>D<sub>6</sub> solution this organoborane and pyridine
form a frustrated Lewis pair. Under mild conditions, <b>1</b> 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<sub>2</sub>Bpin][Ar<sup>F</sup><sub>2</sub>B(H)Me] (<b>3</b>), was characterized in solution by NMR spectroscopy,
which was also confirmed by DFT calculation
