Pyridyl Directed Catalyst-Free trans-Hydroboration of Internal Alkynes

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• 作者：Kang Yuan ; Naoya Suzuki ; Soren K. Mellerup ; Xiang Wang ; Shigehiro Yamaguchi ; Suning Wang
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 19, 2016
• 年：2016
• 卷：18
• 期：4
• 页码：720-723
• 全文大小：330K
• ISSN：1523-7052

文摘

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.