2016•Organic LettersRequires access

Pyridyl Directed Catalyst-Free trans -Hydroboration of Internal Alkynes

Kang Yuan, Naoya Suzuki, Soren K. Mellerup, Xiang Wang, Shigehiro Yamaguchi, Suning Wang

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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Key concepts: Hydroboration, Chemistry, Stereoselectivity, Hydride, Catalysis, Organic chemistry, Combinatorial chemistry, Stereochemistry