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Pyridyl Directed Catalyst-Free trans-Hydroboration of Internal Alkynes
Kang Yuan1, Naoya Suzuki2, Soren K Mellerup1
1Department of Chemistry, Queen's University , Kingston, Ontario K7L 3N6, Canada.
Abstract:
We report the first examples of straightforward trans-hydroboration of internal alkynes at room temperature with 9-BBN, producing five-membered BN-heterocycles. Contrary to conventional cis-hydroboration, we demonstrate that the introduction of a pyridyl group switches the stereoselectivity of the reaction. A hydride migration mechanism has been proposed and supported by DFT calculations for the trans-hydroboration. This new hydroboration approach allows facile construction of new blue fluorescent BN-heterocyclic compounds.
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