Highly Efficient Nickel-Catalyzed Cross-Coupling of Succinic and Glutaric Anhydrides with Organozinc Reagents
A nickel-catalyzed alkylation of succinic and glutaric anhydrides with alkyl- and arylzinc reagents has been developed. A dramatic olefin effect has been investigated resulting in the identification of several styrene-based promoters which show pronounced enhancements in reaction rate. The substrate...
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| Veröffentlicht in: | Journal of the American Chemical Society 2005-01, Vol.127 (1), p.247-254 |
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| container_title | Journal of the American Chemical Society |
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| creator | Bercot, Eric A Rovis, Tomislav |
| description | A nickel-catalyzed alkylation of succinic and glutaric anhydrides with alkyl- and arylzinc reagents has been developed. A dramatic olefin effect has been investigated resulting in the identification of several styrene-based promoters which show pronounced enhancements in reaction rate. The substrate scope with respect to electrophilic and nucleophilic coupling partners has been examined and found to be remarkably broad, allowing for rapid introduction of molecular complexity through the use of functionalized coupling partners. Regioselective alkylation of an unsymmetrical succinic anhydride and a profound effect of pendent coordinating olefins on reaction rate suggest a mechanism involving discrete oxidative addition of the nickel complex into the cyclic anhydride followed by a transmetalation event. |
| doi_str_mv | 10.1021/ja044588b |
| format | Article |
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Am. Chem. Soc</addtitle><description>A nickel-catalyzed alkylation of succinic and glutaric anhydrides with alkyl- and arylzinc reagents has been developed. A dramatic olefin effect has been investigated resulting in the identification of several styrene-based promoters which show pronounced enhancements in reaction rate. The substrate scope with respect to electrophilic and nucleophilic coupling partners has been examined and found to be remarkably broad, allowing for rapid introduction of molecular complexity through the use of functionalized coupling partners. Regioselective alkylation of an unsymmetrical succinic anhydride and a profound effect of pendent coordinating olefins on reaction rate suggest a mechanism involving discrete oxidative addition of the nickel complex into the cyclic anhydride followed by a transmetalation event.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Kinetics and mechanisms</subject><subject>Organic chemistry</subject><subject>Reactivity and mechanisms</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNptkE1vEzEQhi1ERUPgwB9AvoDEYYs_d73HdiltUUWhLeJoTbzexKnjDfauIP31dZSouXAajebRq3cehN5RckIJo5-XQISQSs1eoAmVjBSSsvIlmhBCWFGpkh-j1ykt8yqYoq_QMZUlp6ISE7S6dPOF3-DzrnPG2TDg7848WF80MIDfPNoWN7FPqWj6ce1dmOO-w3ejMS44gyG0-MKPA8S8nIbFpo2utQn_dcMC38Q5hP7RBYNvLcxzdnqDjjrwyb7dzyn69fX8vrksrm8urprT6wK4okMhGGMUWD2rOSV1pbignbRgiDSVUdLAtj_hSglWKyN4SwWtWdkyXkklVM2n6OMudx37P6NNg165ZKz3EGw_Jl1WXBCSxUzRpx1otk9G2-l1dCuIG02J3rrVz24z-34fOs5Wtj2Qe5kZ-LAHIBnwXYRgXDpwZf5LcpW5Yse5NNh_z3eID9tildT3P-70WfNN3f7-yfSXQy6YpJf9GEN295-CT0BnmsI</recordid><startdate>20050112</startdate><enddate>20050112</enddate><creator>Bercot, Eric A</creator><creator>Rovis, Tomislav</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050112</creationdate><title>Highly Efficient Nickel-Catalyzed Cross-Coupling of Succinic and Glutaric Anhydrides with Organozinc Reagents</title><author>Bercot, Eric A ; Rovis, Tomislav</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-42221a29b9310978341f5eac05c7c85ca156303884298c43d141926d237584893</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Kinetics and mechanisms</topic><topic>Organic chemistry</topic><topic>Reactivity and mechanisms</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bercot, Eric A</creatorcontrib><creatorcontrib>Rovis, Tomislav</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bercot, Eric A</au><au>Rovis, Tomislav</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly Efficient Nickel-Catalyzed Cross-Coupling of Succinic and Glutaric Anhydrides with Organozinc Reagents</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. 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Regioselective alkylation of an unsymmetrical succinic anhydride and a profound effect of pendent coordinating olefins on reaction rate suggest a mechanism involving discrete oxidative addition of the nickel complex into the cyclic anhydride followed by a transmetalation event.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15631474</pmid><doi>10.1021/ja044588b</doi><tpages>8</tpages></addata></record> |
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| source | American Chemical Society Journals |
| subjects | Chemistry Exact sciences and technology Kinetics and mechanisms Organic chemistry Reactivity and mechanisms |
| title | Highly Efficient Nickel-Catalyzed Cross-Coupling of Succinic and Glutaric Anhydrides with Organozinc Reagents |
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