Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination
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)diphe...
| Autores: | , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2011 |
| País: | Argentina |
| Institución: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/62006 |
| Acceso en línea: | http://hdl.handle.net/11336/62006 |
| Access Level: | acceso abierto |
| Palabra clave: | Arsine Biphenyl Palladium Ligands https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Sumario: | 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%). © 2011 The Royal Society of Chemistry. |
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