Highly Active Oxime-Derived Palladacycle Complexes for Suzuki−Miyaura and Ullmann-Type Coupling Reactions
Oxime-derived chloro-bridged palladacycles 12 and 13 are efficient complexes for the Suzuki−Miyaura reactions of aryl-, allyl-, and benzyl halides with arylboronic acids. The isolated catalysts are thermally stable, not sensitive to air or moisture, and easily accessible from inexpensive starting ma...
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| Veröffentlicht in: | Journal of organic chemistry 2002-08, Vol.67 (16), p.5588-5594 |
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| container_title | Journal of organic chemistry |
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| creator | Alonso, Diego A Nájera, Carmen Pacheco, Ma Carmen |
| description | Oxime-derived chloro-bridged palladacycles 12 and 13 are efficient complexes for the Suzuki−Miyaura reactions of aryl-, allyl-, and benzyl halides with arylboronic acids. The isolated catalysts are thermally stable, not sensitive to air or moisture, and easily accessible from inexpensive starting materials. The reaction can be performed under aerobic conditions with aryl bromides and chlorides, displaying turnover numbers (TON) of up to 5 × 105 and turnover frequencies (TOF) of up to 198 000 h-1 for aryl bromides. Aryl chlorides undergo the Suzuki reaction with arylboronic acids with TON of up to 4700 and TOF up to 4700 h-1. Even inexpensive and readily available benzyl and allyl chlorides undergo the coupling reaction with good turnover numbers. Complexes of 12 catalyze the syntheses of symmetrical biaryls in good yields via reductive coupling of iodoarenes in the presence of Hünig's base. |
| doi_str_mv | 10.1021/jo025619t |
| format | Article |
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The isolated catalysts are thermally stable, not sensitive to air or moisture, and easily accessible from inexpensive starting materials. The reaction can be performed under aerobic conditions with aryl bromides and chlorides, displaying turnover numbers (TON) of up to 5 × 105 and turnover frequencies (TOF) of up to 198 000 h-1 for aryl bromides. Aryl chlorides undergo the Suzuki reaction with arylboronic acids with TON of up to 4700 and TOF up to 4700 h-1. Even inexpensive and readily available benzyl and allyl chlorides undergo the coupling reaction with good turnover numbers. Complexes of 12 catalyze the syntheses of symmetrical biaryls in good yields via reductive coupling of iodoarenes in the presence of Hünig's base.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo025619t</identifier><identifier>PMID: 12153256</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Catalysis ; Chemistry ; Coordination compounds ; Exact sciences and technology ; General and physical chemistry ; Inorganic chemistry and origins of life ; Noncondensed benzenic compounds ; Organic chemistry ; Preparations and properties ; Theory of reactions, general kinetics. Catalysis. 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Org. Chem</addtitle><description>Oxime-derived chloro-bridged palladacycles 12 and 13 are efficient complexes for the Suzuki−Miyaura reactions of aryl-, allyl-, and benzyl halides with arylboronic acids. The isolated catalysts are thermally stable, not sensitive to air or moisture, and easily accessible from inexpensive starting materials. The reaction can be performed under aerobic conditions with aryl bromides and chlorides, displaying turnover numbers (TON) of up to 5 × 105 and turnover frequencies (TOF) of up to 198 000 h-1 for aryl bromides. Aryl chlorides undergo the Suzuki reaction with arylboronic acids with TON of up to 4700 and TOF up to 4700 h-1. Even inexpensive and readily available benzyl and allyl chlorides undergo the coupling reaction with good turnover numbers. Complexes of 12 catalyze the syntheses of symmetrical biaryls in good yields via reductive coupling of iodoarenes in the presence of Hünig's base.</description><subject>Catalysis</subject><subject>Chemistry</subject><subject>Coordination compounds</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Inorganic chemistry and origins of life</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Theory of reactions, general kinetics. Catalysis. 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Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Alonso, Diego A</creatorcontrib><creatorcontrib>Nájera, Carmen</creatorcontrib><creatorcontrib>Pacheco, Ma Carmen</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Alonso, Diego A</au><au>Nájera, Carmen</au><au>Pacheco, Ma Carmen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly Active Oxime-Derived Palladacycle Complexes for Suzuki−Miyaura and Ullmann-Type Coupling Reactions</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2002-08-09</date><risdate>2002</risdate><volume>67</volume><issue>16</issue><spage>5588</spage><epage>5594</epage><pages>5588-5594</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Oxime-derived chloro-bridged palladacycles 12 and 13 are efficient complexes for the Suzuki−Miyaura reactions of aryl-, allyl-, and benzyl halides with arylboronic acids. The isolated catalysts are thermally stable, not sensitive to air or moisture, and easily accessible from inexpensive starting materials. The reaction can be performed under aerobic conditions with aryl bromides and chlorides, displaying turnover numbers (TON) of up to 5 × 105 and turnover frequencies (TOF) of up to 198 000 h-1 for aryl bromides. Aryl chlorides undergo the Suzuki reaction with arylboronic acids with TON of up to 4700 and TOF up to 4700 h-1. Even inexpensive and readily available benzyl and allyl chlorides undergo the coupling reaction with good turnover numbers. Complexes of 12 catalyze the syntheses of symmetrical biaryls in good yields via reductive coupling of iodoarenes in the presence of Hünig's base.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12153256</pmid><doi>10.1021/jo025619t</doi><tpages>7</tpages></addata></record> |
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| source | ACS Publications |
| subjects | Catalysis Chemistry Coordination compounds Exact sciences and technology General and physical chemistry Inorganic chemistry and origins of life Noncondensed benzenic compounds Organic chemistry Preparations and properties Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Highly Active Oxime-Derived Palladacycle Complexes for Suzuki−Miyaura and Ullmann-Type Coupling Reactions |
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