Tetrahydroxydiboron-Mediated Palladium-Catalyzed Transfer Hydrogenation and Deuteriation of Alkenes and Alkynes Using Water as the Stoichiometric H or D Atom Donor

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• 作者：Steven P. Cummings ; Thanh-Ngoc Le ; Gilberto E. Fernandez ; Lorenzo G. Quiambao ; Benjamin J. Stokes
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：May 18, 2016
• 年：2016
• 卷：138
• 期：19
• 页码：6107-6110
• 全文大小：366K
• 年卷期：0
• ISSN：1520-5126

文摘

There are few examples of catalytic transfer hydrogenations of simple alkenes and alkynes that use water as a stoichiometric H or D atom donor. We have found that diboron reagents efficiently mediate the transfer of H or D atoms from water directly onto unsaturated C–C bonds using a palladium catalyst. This reaction is conducted on a broad variety of alkenes and alkynes at ambient temperature, and boric acid is the sole byproduct. Mechanistic experiments suggest that this reaction is made possible by a hydrogen atom transfer from water that generates a Pd–hydride intermediate. Importantly, complete deuterium incorporation from stoichiometric D₂O has also been achieved.