3 years ago

Exploring the Influence of Phosphine Ligation on the Gold-Catalyzed Hydrohydrazination of Terminal Alkynes at Room Temperature

Exploring the Influence of Phosphine Ligation on the Gold-Catalyzed Hydrohydrazination of Terminal Alkynes at Room Temperature
Michael J. Ferguson, Alicia J. Chisholm, Preston M. MacQueen, Mark Stradiotto, Robert McDonald, Nicolas L. Rotta-Loria
The synthesis and/or NMR/X-ray characterization of a new series of (L)AuCl complexes is reported, featuring BippyPhos, AdJohnPhos, silyl ether based ligands including OTips-DalPhos, and PAd-DalPhos. These complexes, along with previously reported analogues featuring cataCXium-A, tBuJohnPhos, and Mor-DalPhos, were screened as precatalysts using LiB(C6F5)4·2.5Et2O as an activator in the hydrohydrazination of terminal aryl alkynes with hydrazine hydrate under unprecedentedly mild conditions (25 °C, 1 mol % Au). The precatalyst (cataCXium-A)AuCl proved to be particularly effective in such transformations, demonstrating useful scope.

Publisher URL: http://dx.doi.org/10.1021/acs.organomet.7b00373

DOI: 10.1021/acs.organomet.7b00373

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