1335138-41-4Relevant academic research and scientific papers
Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction
Quinteros, Gisela J.,Uberman, Paula M.,Martín, Sandra E.
, p. 2698 - 2705 (2015/04/27)
Biphenyl-based arsine ligands were prepared in two-step fashion by Pd-catalyzed arsination and microwave-assisted Suzuki-Miyaura coupling, providing sterically demanding arsine ligands in overall isolated yields up to 82 % as air-stable solids. Short reaction times were achieved with the assistance of microwave irradiation in the direct and simple described protocol for the synthesis of biarylarsine ligands. The activities of the biphenyl arsine ligands were explored in Pd-catalyzed Heck coupling. As a general trend, the ligands with "blocked" ortho-positions on the non-arsine-containing ring of the biphenyl backbone performed more efficiently in the coupling reaction. This catalytic system allowed several interesting stilbenes to be obtained in very good yields. Sterically demanding biphenyl-based arsine ligands were prepared in high overall yields by microwave-assisted Suzuki-Miyaura coupling. The ligands were evaluated in the Pd-catalyzed Heck coupling reaction; the most active were those with "blocked" ortho-positions on the non-arsine-containing ring of the biphenyl backbone.
Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination
Uberman, Paula M.,Lanteri, Mario N.,Parajon Puenzo, Sol C.,Martin, Sandra E.
, p. 9229 - 9237 (2011/11/05)
A versatile and efficient approach for the synthesis of new biphenyl-based arsine ligands, by a Pd-catalyzed arsination to introduce the -AsPh2 moiety, and then a Suzuki-Miyaura cross-coupling for biaryl construction is reported. By Pd-catalyzed arsination with n-Bu3SnAsPh2 (1), (2-bromophenyl)diphenylarsine (2, 83%) was obtained. The Suzuki-Miyaura reaction between the bromoarsine 2 and aryl boronic acids bearing different substituents provided biarylarsine ligands (80-99%). The efficiency of catalysts derived from the new biarylarsine ligands was evaluated in the Pd-catalyzed arsination with perfluoroalkyl iodides (RfI). Outstanding activities of catalysts derived from Pd/methoxybiarylarsine ligands were found in this coupling reaction affording perfluoroalkyl arsines in very good yields (57-100%).
