A Palladium(II)-Catalyzed CH Activation Cascade Sequence for Polyheterocycle Formation
Polyheterocycles are found in many natural products and are useful moieties in functional materials and drug design. As part of a program towards the synthesis of Stemona alkaloids, a novel palladium(II)‐catalyzed CH activation strategy for the construction of such systems has been developed. Start...
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| Veröffentlicht in: | Angewandte Chemie 2015-05, Vol.127 (22), p.6596-6600 |
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| container_title | Angewandte Chemie |
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| creator | Cooper, Stephen P. Booker-Milburn, Kevin I. |
| description | Polyheterocycles are found in many natural products and are useful moieties in functional materials and drug design. As part of a program towards the synthesis of Stemona alkaloids, a novel palladium(II)‐catalyzed CH activation strategy for the construction of such systems has been developed. Starting from simple 1,3‐dienyl‐substituted heterocycles, a large range of polycyclic systems containing pyrrole, indole, furan and thiophene moieties can be synthesized in a single step.
Nicht übertreiben: Eine Palladium(II)‐katalysierte C‐H‐Aktivierungssequenz für die Synthese von Polyheterocyclen wird beschrieben. Die Aromatisierung der anfänglich gebildeten Dihydro‐Spezies wird mit einem Chinon als Oxidationsmittel bewirkt. In einigen Fällen ermöglichte der Einsatz von 1 Äquivalent des Oxidationsmittel die Isolierung der Dihydro‐Spezies als einzelnes Isomer (siehe Schema; X=NMe, O, S). |
| doi_str_mv | 10.1002/ange.201501037 |
| format | Article |
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Nicht übertreiben: Eine Palladium(II)‐katalysierte C‐H‐Aktivierungssequenz für die Synthese von Polyheterocyclen wird beschrieben. Die Aromatisierung der anfänglich gebildeten Dihydro‐Spezies wird mit einem Chinon als Oxidationsmittel bewirkt. In einigen Fällen ermöglichte der Einsatz von 1 Äquivalent des Oxidationsmittel die Isolierung der Dihydro‐Spezies als einzelnes Isomer (siehe Schema; X=NMe, O, S).</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201501037</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Activation ; Alkaloids ; C-H-Aktivierung ; Cascades ; Design engineering ; Dominoreaktionen ; Formations ; Furans ; Heterocyclen ; Homogene Katalyse ; Palladium ; Strategy ; Synthesis ; Thiophenes</subject><ispartof>Angewandte Chemie, 2015-05, Vol.127 (22), p.6596-6600</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2057-b18f93caf93e4c7a782b39d1b852295930612b158642676d4b7d2418ce8f91a33</citedby><cites>FETCH-LOGICAL-c2057-b18f93caf93e4c7a782b39d1b852295930612b158642676d4b7d2418ce8f91a33</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%2Fange.201501037$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201501037$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Cooper, Stephen P.</creatorcontrib><creatorcontrib>Booker-Milburn, Kevin I.</creatorcontrib><title>A Palladium(II)-Catalyzed CH Activation Cascade Sequence for Polyheterocycle Formation</title><title>Angewandte Chemie</title><addtitle>Angew. Chem</addtitle><description>Polyheterocycles are found in many natural products and are useful moieties in functional materials and drug design. As part of a program towards the synthesis of Stemona alkaloids, a novel palladium(II)‐catalyzed CH activation strategy for the construction of such systems has been developed. Starting from simple 1,3‐dienyl‐substituted heterocycles, a large range of polycyclic systems containing pyrrole, indole, furan and thiophene moieties can be synthesized in a single step.
Nicht übertreiben: Eine Palladium(II)‐katalysierte C‐H‐Aktivierungssequenz für die Synthese von Polyheterocyclen wird beschrieben. Die Aromatisierung der anfänglich gebildeten Dihydro‐Spezies wird mit einem Chinon als Oxidationsmittel bewirkt. In einigen Fällen ermöglichte der Einsatz von 1 Äquivalent des Oxidationsmittel die Isolierung der Dihydro‐Spezies als einzelnes Isomer (siehe Schema; X=NMe, O, S).</description><subject>Activation</subject><subject>Alkaloids</subject><subject>C-H-Aktivierung</subject><subject>Cascades</subject><subject>Design engineering</subject><subject>Dominoreaktionen</subject><subject>Formations</subject><subject>Furans</subject><subject>Heterocyclen</subject><subject>Homogene Katalyse</subject><subject>Palladium</subject><subject>Strategy</subject><subject>Synthesis</subject><subject>Thiophenes</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkUtOwzAQhi0EEqWwZZ1lWaSMnYeTZRT1JVWlEo-WleU4EwikDdgpEK7DQTgSVyAlqGLHZmbzfaOZfwg5pdCnAOxcru-wz4B6QMHhe6RDPUZth3t8n3QAXNcOmBsekiNjHgDAZzzskNvImsuikGm-WfUmkzM7lpUs6ndMrfjr43NsRarKX2SVl2srlkbJFK1LfN7gWqGVldqal0V9jxXqUtWqQGtY6tUPfkwOMlkYPPntXXI9HFzFY3t6MZrE0dRWDDxuJzTIQkfJpqCruOQBS5wwpUngMRZ6oQM-ZQn1At9lPvdTN-Epc2mgsPGodJwu6bVzn3TZ7GUqscqNwuamNZYbIyhv8gDgDBq036JKl8ZozMSTzldS14KC2GYothmKXYaNELbCa15g_Q8totlo8Ne1Wzc3Fb7tXKkfhc-br4jFbCQW46G_vFm6wne-AcekhIs</recordid><startdate>20150526</startdate><enddate>20150526</enddate><creator>Cooper, Stephen P.</creator><creator>Booker-Milburn, Kevin I.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20150526</creationdate><title>A Palladium(II)-Catalyzed CH Activation Cascade Sequence for Polyheterocycle Formation</title><author>Cooper, Stephen P. ; Booker-Milburn, Kevin I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2057-b18f93caf93e4c7a782b39d1b852295930612b158642676d4b7d2418ce8f91a33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Activation</topic><topic>Alkaloids</topic><topic>C-H-Aktivierung</topic><topic>Cascades</topic><topic>Design engineering</topic><topic>Dominoreaktionen</topic><topic>Formations</topic><topic>Furans</topic><topic>Heterocyclen</topic><topic>Homogene Katalyse</topic><topic>Palladium</topic><topic>Strategy</topic><topic>Synthesis</topic><topic>Thiophenes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cooper, Stephen P.</creatorcontrib><creatorcontrib>Booker-Milburn, Kevin I.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cooper, Stephen P.</au><au>Booker-Milburn, Kevin I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Palladium(II)-Catalyzed CH Activation Cascade Sequence for Polyheterocycle Formation</atitle><jtitle>Angewandte Chemie</jtitle><addtitle>Angew. Chem</addtitle><date>2015-05-26</date><risdate>2015</risdate><volume>127</volume><issue>22</issue><spage>6596</spage><epage>6600</epage><pages>6596-6600</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>Polyheterocycles are found in many natural products and are useful moieties in functional materials and drug design. As part of a program towards the synthesis of Stemona alkaloids, a novel palladium(II)‐catalyzed CH activation strategy for the construction of such systems has been developed. Starting from simple 1,3‐dienyl‐substituted heterocycles, a large range of polycyclic systems containing pyrrole, indole, furan and thiophene moieties can be synthesized in a single step.
Nicht übertreiben: Eine Palladium(II)‐katalysierte C‐H‐Aktivierungssequenz für die Synthese von Polyheterocyclen wird beschrieben. Die Aromatisierung der anfänglich gebildeten Dihydro‐Spezies wird mit einem Chinon als Oxidationsmittel bewirkt. In einigen Fällen ermöglichte der Einsatz von 1 Äquivalent des Oxidationsmittel die Isolierung der Dihydro‐Spezies als einzelnes Isomer (siehe Schema; X=NMe, O, S).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ange.201501037</doi><tpages>5</tpages></addata></record> |
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| subjects | Activation Alkaloids C-H-Aktivierung Cascades Design engineering Dominoreaktionen Formations Furans Heterocyclen Homogene Katalyse Palladium Strategy Synthesis Thiophenes |
| title | A Palladium(II)-Catalyzed CH Activation Cascade Sequence for Polyheterocycle Formation |
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