Synthesis of Benzofuran Derivatives through Cascade Radical Cyclization/Intermolecular Coupling of 2‐Azaallyls
Benzofurans are among the most popular structural units in bioactive natural products, however, the synthesis of such structures by radical cyclization cascade reactions is rare. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives t...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2019-02, Vol.58 (9), p.2826-2830 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Deng, Guogang Li, Minyan Yu, Kaili Liu, Chunxiang Liu, Zhengfen Duan, Shengzu Chen, Wen Yang, Xiaodong Zhang, Hongbin Walsh, Patrick J. |
| description | Benzofurans are among the most popular structural units in bioactive natural products, however, the synthesis of such structures by radical cyclization cascade reactions is rare. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade mechanism. Single‐electron transfer (SET) from 2‐azaallyl anions to 2‐iodo aryl allenyl ethers initiates a radical cyclization that is followed by intermolecular radical–radical coupling. This expedient approach enables the synthesis of a range of polycyclic benzofurans that would otherwise be difficult to prepare.
Well behaved radicals: a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade mechanism is presented. SET from 2‐azaallyl anions to 2‐iodo aryl allenyl ethers initiates a radical cyclization that is followed by intermolecular radical–radical coupling. |
| doi_str_mv | 10.1002/anie.201812369 |
| format | Article |
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Well behaved radicals: a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade mechanism is presented. SET from 2‐azaallyl anions to 2‐iodo aryl allenyl ethers initiates a radical cyclization that is followed by intermolecular radical–radical coupling.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201812369</identifier><identifier>PMID: 30624843</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Anions ; Aromatic compounds ; azaallyl anions ; Benzofuran ; benzofurylethylamine ; Cascade chemical reactions ; cascade reactions ; Chemical synthesis ; Coupling ; Derivatives ; Electron transfer ; Ethers ; Natural products ; radical coupling ; radical cyclization</subject><ispartof>Angewandte Chemie International Edition, 2019-02, Vol.58 (9), p.2826-2830</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4399-6d098a1617f3315552f84a113c03cf8d1e891aedbc34de67d9298ed097aa3fe23</citedby><cites>FETCH-LOGICAL-c4399-6d098a1617f3315552f84a113c03cf8d1e891aedbc34de67d9298ed097aa3fe23</cites><orcidid>0000-0002-8466-5418 ; 0000-0001-8392-4150 ; 0000-0002-2516-2634</orcidid></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.201812369$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201812369$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30624843$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Deng, Guogang</creatorcontrib><creatorcontrib>Li, Minyan</creatorcontrib><creatorcontrib>Yu, Kaili</creatorcontrib><creatorcontrib>Liu, Chunxiang</creatorcontrib><creatorcontrib>Liu, Zhengfen</creatorcontrib><creatorcontrib>Duan, Shengzu</creatorcontrib><creatorcontrib>Chen, Wen</creatorcontrib><creatorcontrib>Yang, Xiaodong</creatorcontrib><creatorcontrib>Zhang, Hongbin</creatorcontrib><creatorcontrib>Walsh, Patrick J.</creatorcontrib><title>Synthesis of Benzofuran Derivatives through Cascade Radical Cyclization/Intermolecular Coupling of 2‐Azaallyls</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Benzofurans are among the most popular structural units in bioactive natural products, however, the synthesis of such structures by radical cyclization cascade reactions is rare. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade mechanism. Single‐electron transfer (SET) from 2‐azaallyl anions to 2‐iodo aryl allenyl ethers initiates a radical cyclization that is followed by intermolecular radical–radical coupling. This expedient approach enables the synthesis of a range of polycyclic benzofurans that would otherwise be difficult to prepare.
Well behaved radicals: a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade mechanism is presented. SET from 2‐azaallyl anions to 2‐iodo aryl allenyl ethers initiates a radical cyclization that is followed by intermolecular radical–radical coupling.</description><subject>Anions</subject><subject>Aromatic compounds</subject><subject>azaallyl anions</subject><subject>Benzofuran</subject><subject>benzofurylethylamine</subject><subject>Cascade chemical reactions</subject><subject>cascade reactions</subject><subject>Chemical synthesis</subject><subject>Coupling</subject><subject>Derivatives</subject><subject>Electron transfer</subject><subject>Ethers</subject><subject>Natural products</subject><subject>radical coupling</subject><subject>radical cyclization</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqF0btOHDEUBmALBQEhaSnRSGnSzOLLXOxyMyGwEgIpl3p08Jxhjbz2xp4hmq3yCHnGPAleLRApDZVP8Z1fR_4JOWF0xijlZ-AMzjhlknFRqT1yxErOclHX4k2aCyHyWpbskLyN8T55KWl1QA4FrXghC3FE1t8mNywxmpj5PvuEbuP7MYDLPmMwDzCYB4zZsAx-vFtmDUQNHWZfoTMabNZM2ppNQt6dLdyAYeUt6tFCyBo_rq1xd9tU_vf3n_kGwNrJxndkvwcb8f3Te0x-fDn_3lzmVzcXi2Z-letCKJVXHVUSWMXqXghWliXvZQGMCU2F7mXHUCoG2N1qUXRY1Z3iSmJaqgFEj1wck4-73HXwP0eMQ7syUaO14NCPseWsKquyVuWWfviP3vsxuHRdUpIXXMhCJjXbKR18jAH7dh3MCsLUMtpuu2i3XbQvXaSF06fY8XaF3Qt__vwE1A78MhanV-La-fXi_F_4IxGCl5s</recordid><startdate>20190225</startdate><enddate>20190225</enddate><creator>Deng, Guogang</creator><creator>Li, Minyan</creator><creator>Yu, Kaili</creator><creator>Liu, Chunxiang</creator><creator>Liu, Zhengfen</creator><creator>Duan, Shengzu</creator><creator>Chen, Wen</creator><creator>Yang, Xiaodong</creator><creator>Zhang, Hongbin</creator><creator>Walsh, Patrick J.</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8466-5418</orcidid><orcidid>https://orcid.org/0000-0001-8392-4150</orcidid><orcidid>https://orcid.org/0000-0002-2516-2634</orcidid></search><sort><creationdate>20190225</creationdate><title>Synthesis of Benzofuran Derivatives through Cascade Radical Cyclization/Intermolecular Coupling of 2‐Azaallyls</title><author>Deng, Guogang ; Li, Minyan ; Yu, Kaili ; Liu, Chunxiang ; Liu, Zhengfen ; Duan, Shengzu ; Chen, Wen ; Yang, Xiaodong ; Zhang, Hongbin ; Walsh, Patrick J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4399-6d098a1617f3315552f84a113c03cf8d1e891aedbc34de67d9298ed097aa3fe23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Anions</topic><topic>Aromatic compounds</topic><topic>azaallyl anions</topic><topic>Benzofuran</topic><topic>benzofurylethylamine</topic><topic>Cascade chemical reactions</topic><topic>cascade reactions</topic><topic>Chemical synthesis</topic><topic>Coupling</topic><topic>Derivatives</topic><topic>Electron transfer</topic><topic>Ethers</topic><topic>Natural products</topic><topic>radical coupling</topic><topic>radical cyclization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Deng, Guogang</creatorcontrib><creatorcontrib>Li, Minyan</creatorcontrib><creatorcontrib>Yu, Kaili</creatorcontrib><creatorcontrib>Liu, Chunxiang</creatorcontrib><creatorcontrib>Liu, Zhengfen</creatorcontrib><creatorcontrib>Duan, Shengzu</creatorcontrib><creatorcontrib>Chen, Wen</creatorcontrib><creatorcontrib>Yang, Xiaodong</creatorcontrib><creatorcontrib>Zhang, Hongbin</creatorcontrib><creatorcontrib>Walsh, Patrick J.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Deng, Guogang</au><au>Li, Minyan</au><au>Yu, Kaili</au><au>Liu, Chunxiang</au><au>Liu, Zhengfen</au><au>Duan, Shengzu</au><au>Chen, Wen</au><au>Yang, Xiaodong</au><au>Zhang, Hongbin</au><au>Walsh, Patrick J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Benzofuran Derivatives through Cascade Radical Cyclization/Intermolecular Coupling of 2‐Azaallyls</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2019-02-25</date><risdate>2019</risdate><volume>58</volume><issue>9</issue><spage>2826</spage><epage>2830</epage><pages>2826-2830</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Benzofurans are among the most popular structural units in bioactive natural products, however, the synthesis of such structures by radical cyclization cascade reactions is rare. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade mechanism. Single‐electron transfer (SET) from 2‐azaallyl anions to 2‐iodo aryl allenyl ethers initiates a radical cyclization that is followed by intermolecular radical–radical coupling. This expedient approach enables the synthesis of a range of polycyclic benzofurans that would otherwise be difficult to prepare.
Well behaved radicals: a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade mechanism is presented. SET from 2‐azaallyl anions to 2‐iodo aryl allenyl ethers initiates a radical cyclization that is followed by intermolecular radical–radical coupling.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30624843</pmid><doi>10.1002/anie.201812369</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-8466-5418</orcidid><orcidid>https://orcid.org/0000-0001-8392-4150</orcidid><orcidid>https://orcid.org/0000-0002-2516-2634</orcidid></addata></record> |
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| subjects | Anions Aromatic compounds azaallyl anions Benzofuran benzofurylethylamine Cascade chemical reactions cascade reactions Chemical synthesis Coupling Derivatives Electron transfer Ethers Natural products radical coupling radical cyclization |
| title | Synthesis of Benzofuran Derivatives through Cascade Radical Cyclization/Intermolecular Coupling of 2‐Azaallyls |
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