Palladium-Catalyzed Direct CH Arylation of Isoxazoles at the 5-Position
A palladium‐catalyzed direct arylation of isoxazoles with aryl iodides has been achieved. The CH bond at the 5‐position is activated selectively to give coupling products in moderate to good yields. This direct arylation was applied to the synthesis of a spiro‐type chiral ligand, which proved to be...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-08, Vol.54 (33), p.9572-9576 |
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| creator | Shigenobu, Masashi Takenaka, Kazuhiro Sasai, Hiroaki |
| description | A palladium‐catalyzed direct arylation of isoxazoles with aryl iodides has been achieved. The CH bond at the 5‐position is activated selectively to give coupling products in moderate to good yields. This direct arylation was applied to the synthesis of a spiro‐type chiral ligand, which proved to be most effective to the palladium‐catalyzed tandem cyclization of a dialkenyl alcohol.
Knock your ′sox′ off: A palladium catalyst promotes the cross‐coupling of isoxazoles with aryl iodides through the selective CH bond activation at the 5‐position of the heteroaromatic compound. The use of 1,2‐bis(diphenylphosphino)benzene as the ligand and silver fluoride as the activator was found to be crucial for this direct arylation. FG=functional group. |
| doi_str_mv | 10.1002/anie.201504552 |
| format | Article |
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Knock your ′sox′ off: A palladium catalyst promotes the cross‐coupling of isoxazoles with aryl iodides through the selective CH bond activation at the 5‐position of the heteroaromatic compound. The use of 1,2‐bis(diphenylphosphino)benzene as the ligand and silver fluoride as the activator was found to be crucial for this direct arylation. FG=functional group.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201504552</identifier><identifier>PMID: 26130462</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Activation ; Aromatic compounds ; arylation ; Bonding ; Cross coupling ; CH activation ; Heteroaromatic compounds ; heterocycles ; Iodides ; Joining ; Ligands ; palladium</subject><ispartof>Angewandte Chemie International Edition, 2015-08, Vol.54 (33), p.9572-9576</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5892-4bb78c4f98bf92a55c3b9320133c471cf9ec94b2c1e9d88e09e38717a95606d93</citedby><cites>FETCH-LOGICAL-c5892-4bb78c4f98bf92a55c3b9320133c471cf9ec94b2c1e9d88e09e38717a95606d93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201504552$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201504552$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26130462$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shigenobu, Masashi</creatorcontrib><creatorcontrib>Takenaka, Kazuhiro</creatorcontrib><creatorcontrib>Sasai, Hiroaki</creatorcontrib><title>Palladium-Catalyzed Direct CH Arylation of Isoxazoles at the 5-Position</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A palladium‐catalyzed direct arylation of isoxazoles with aryl iodides has been achieved. The CH bond at the 5‐position is activated selectively to give coupling products in moderate to good yields. This direct arylation was applied to the synthesis of a spiro‐type chiral ligand, which proved to be most effective to the palladium‐catalyzed tandem cyclization of a dialkenyl alcohol.
Knock your ′sox′ off: A palladium catalyst promotes the cross‐coupling of isoxazoles with aryl iodides through the selective CH bond activation at the 5‐position of the heteroaromatic compound. The use of 1,2‐bis(diphenylphosphino)benzene as the ligand and silver fluoride as the activator was found to be crucial for this direct arylation. FG=functional group.</description><subject>Activation</subject><subject>Aromatic compounds</subject><subject>arylation</subject><subject>Bonding</subject><subject>Cross coupling</subject><subject>CH activation</subject><subject>Heteroaromatic compounds</subject><subject>heterocycles</subject><subject>Iodides</subject><subject>Joining</subject><subject>Ligands</subject><subject>palladium</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqNkMtOwkAUhidGI4huXZou3RTn2plZErwhBF1oWE6m09M4Wih2SgRfxwfxkXwFS1DiTlfnJOf7_-R8CB0T3CUY0zM789ClmAjMhaA7qE0EJTGTku02O2cslkqQFjoI4anhlcLJPmrRhDDME9pGN3e2KGzmF9O4b2tbrN4gi859Ba6O-p_vH9dRr1oVtvblLCrzaBDKpX0rCwiRraP6ESIR35XBr--HaC-3RYCj79lBD5cX9_3reHR7Nej3RrETStOYp6lUjudapbmmVgjHUs2aFxhzXBKXa3Cap9QR0JlSgDUwJYm0WiQ4yTTroNNN77wqXxYQajP1wUHzxgzKRTBEci4xZ5T8A8WEaqaxatDuBnVVGUIFuZlXfmqrlSHYrFWbtWqzVd0ETr67F-kUsi3-47YB9AZ49QWs_qgzvfHg4nd5vMn6UMNym7XVs0kkk8JMxldmyIeTyRCPjWZfU4SZBA</recordid><startdate>20150810</startdate><enddate>20150810</enddate><creator>Shigenobu, Masashi</creator><creator>Takenaka, Kazuhiro</creator><creator>Sasai, Hiroaki</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20150810</creationdate><title>Palladium-Catalyzed Direct CH Arylation of Isoxazoles at the 5-Position</title><author>Shigenobu, Masashi ; Takenaka, Kazuhiro ; Sasai, Hiroaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5892-4bb78c4f98bf92a55c3b9320133c471cf9ec94b2c1e9d88e09e38717a95606d93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Activation</topic><topic>Aromatic compounds</topic><topic>arylation</topic><topic>Bonding</topic><topic>Cross coupling</topic><topic>CH activation</topic><topic>Heteroaromatic compounds</topic><topic>heterocycles</topic><topic>Iodides</topic><topic>Joining</topic><topic>Ligands</topic><topic>palladium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shigenobu, Masashi</creatorcontrib><creatorcontrib>Takenaka, Kazuhiro</creatorcontrib><creatorcontrib>Sasai, Hiroaki</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shigenobu, Masashi</au><au>Takenaka, Kazuhiro</au><au>Sasai, Hiroaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-Catalyzed Direct CH Arylation of Isoxazoles at the 5-Position</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2015-08-10</date><risdate>2015</risdate><volume>54</volume><issue>33</issue><spage>9572</spage><epage>9576</epage><pages>9572-9576</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A palladium‐catalyzed direct arylation of isoxazoles with aryl iodides has been achieved. The CH bond at the 5‐position is activated selectively to give coupling products in moderate to good yields. This direct arylation was applied to the synthesis of a spiro‐type chiral ligand, which proved to be most effective to the palladium‐catalyzed tandem cyclization of a dialkenyl alcohol.
Knock your ′sox′ off: A palladium catalyst promotes the cross‐coupling of isoxazoles with aryl iodides through the selective CH bond activation at the 5‐position of the heteroaromatic compound. The use of 1,2‐bis(diphenylphosphino)benzene as the ligand and silver fluoride as the activator was found to be crucial for this direct arylation. FG=functional group.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26130462</pmid><doi>10.1002/anie.201504552</doi><tpages>5</tpages></addata></record> |
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| subjects | Activation Aromatic compounds arylation Bonding Cross coupling CH activation Heteroaromatic compounds heterocycles Iodides Joining Ligands palladium |
| title | Palladium-Catalyzed Direct CH Arylation of Isoxazoles at the 5-Position |
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