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 -AsPh(2) moiety, and then a Suzuki-Miyaura cross-coupling for biaryl construction is reported. By Pd-catalyzed arsination with n-Bu(3)SnAsPh(2) (1), (2-bromophenyl...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2011-01, Vol.40 (36), p.9229-9237 |
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| container_issue | 36 |
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| container_title | Dalton transactions : an international journal of inorganic chemistry |
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| creator | Uberman, Paula M Lanteri, Mario N Puenzo, Sol C Parajón Martín, Sandra E |
| description | A versatile and efficient approach for the synthesis of new biphenyl-based arsine ligands, by a Pd-catalyzed arsination to introduce the -AsPh(2) moiety, and then a Suzuki-Miyaura cross-coupling for biaryl construction is reported. By Pd-catalyzed arsination with n-Bu(3)SnAsPh(2) (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 (R(f)I). Outstanding activities of catalysts derived from Pd/methoxybiarylarsine ligands were found in this coupling reaction affording perfluoroalkyl arsines in very good yields (57-100%). |
| doi_str_mv | 10.1039/c1dt10207a |
| format | Article |
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By Pd-catalyzed arsination with n-Bu(3)SnAsPh(2) (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 (R(f)I). 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By Pd-catalyzed arsination with n-Bu(3)SnAsPh(2) (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 (R(f)I). Outstanding activities of catalysts derived from Pd/methoxybiarylarsine ligands were found in this coupling reaction affording perfluoroalkyl arsines in very good yields (57-100%).</description><subject>Catalysis</subject><subject>Catalysts</subject><subject>Iodides</subject><subject>Joining</subject><subject>Ligands</subject><subject>Palladium</subject><subject>Perfluoroalkyls</subject><subject>Synthesis</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkUlLw0AYhgdRbK1e_AEyN0WIzpLMcpTiBhWF6jnMlnY0TWImEdJfb2oXb3r6lvfhubwAnGJ0hRGV1wbbBiOCuNoDQxxzHklC4_3dTtgAHIXwjhAhKCGHYECwIFJQNARf065o5i74AMsMal_NXdHlkVbBWajq4AsHcz9ThQ1Qd3DaLtsPHz35TrW1gqZsq9wXM9jnsNf4Gqqq_xjV-LKATQlfbNQfKu-WW99PdAwOMpUHd7KZI_B2d_s6fogmz_eP45tJZKjgTcQYJ5Q6jhS3WaaNoI5xwRPOtaWxtpI4iTBjLjEKxUQ4qZyOWUYxYoYJRkfgfO2t6vKzdaFJFz4Yl-eqcGUbUsmoiCXG_F9SCM4TQfjKefEn2csQEpIJ2qOXa9TUZQi1y9Kq9gtVdylG6aq79Le7Hj7beFu9cHaHbsui38K2la0</recordid><startdate>20110101</startdate><enddate>20110101</enddate><creator>Uberman, Paula M</creator><creator>Lanteri, Mario N</creator><creator>Puenzo, Sol C Parajón</creator><creator>Martín, Sandra E</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SP</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>20110101</creationdate><title>Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination</title><author>Uberman, Paula M ; Lanteri, Mario N ; Puenzo, Sol C Parajón ; Martín, Sandra E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c387t-667233e70a7dffbc83e6787577bd34bd92e90166e5ca0428e9aeb46f3106c6863</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Catalysis</topic><topic>Catalysts</topic><topic>Iodides</topic><topic>Joining</topic><topic>Ligands</topic><topic>Palladium</topic><topic>Perfluoroalkyls</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Uberman, Paula M</creatorcontrib><creatorcontrib>Lanteri, Mario N</creatorcontrib><creatorcontrib>Puenzo, Sol C Parajón</creatorcontrib><creatorcontrib>Martín, Sandra E</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Uberman, Paula M</au><au>Lanteri, Mario N</au><au>Puenzo, Sol C Parajón</au><au>Martín, Sandra E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2011-01-01</date><risdate>2011</risdate><volume>40</volume><issue>36</issue><spage>9229</spage><epage>9237</epage><pages>9229-9237</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>A versatile and efficient approach for the synthesis of new biphenyl-based arsine ligands, by a Pd-catalyzed arsination to introduce the -AsPh(2) moiety, and then a Suzuki-Miyaura cross-coupling for biaryl construction is reported. 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| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2011-01, Vol.40 (36), p.9229-9237 |
| issn | 1477-9226 1477-9234 |
| language | eng |
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| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | Catalysis Catalysts Iodides Joining Ligands Palladium Perfluoroalkyls Synthesis |
| title | Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination |
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