title: Pyridyl Directed Catalyst-Free trans-Hydroboration of Internal Alkynes.
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.
authors.affiliation: Department of Chemistry, Queen's University , Kingston, Ontario K7L 3N6, Canada.
authors.forename: Kang
authors.initials: K
authors.lastname: Yuan
authors.affiliation: Department of Chemistry, Graduate School of Science, Nagoya University , Furo, Chikusa, Nagoya 464-8602, Japan.
authors.forename: Naoya
authors.initials: N
authors.lastname: Suzuki
authors.affiliation: Department of Chemistry, Queen's University , Kingston, Ontario K7L 3N6, Canada.
authors.forename: Soren K
authors.initials: SK
authors.lastname: Mellerup
authors.affiliation: Department of Chemistry, Queen's University , Kingston, Ontario K7L 3N6, Canada.
authors.forename: Xiang
authors.initials: X
authors.lastname: Wang
authors.affiliation: Department of Chemistry, Graduate School of Science, Nagoya University , Furo, Chikusa, Nagoya 464-8602, Japan.
authors.forename: Shigehiro
authors.initials: S
authors.lastname: Yamaguchi
authors.affiliation: Department of Chemistry, Queen's University , Kingston, Ontario K7L 3N6, Canada.|Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, School of Chemistry, Beijing Institute of Technology , Beijing 100081, P. R. China.
authors.forename: Suning
authors.initials: S
authors.lastname: Wang