Iron-catalyzed reductive cyclization reaction of 1,6-enynes for the synthesis of 3-acylbenzofurans and thiophenes
A facile synthesis of 3-acylbenzofurans and thiophenes via iron( ii )-catalyzed reductive cyclization of 1,6-enynes has been developed. A sequence involving hydrogen atom transfer (HAT)/cyclization and oxygen insertion has been proposed and confirmed by isotope experiments. This benign strategy prov...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2019-02, Vol.6 (3), p.342-346 |
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| container_title | Organic Chemistry Frontiers |
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| creator | Xia, Xiao-Feng He, Wei Zhang, Guo-Wei Wang, Dawei |
| description | A facile synthesis of 3-acylbenzofurans and thiophenes via iron( ii )-catalyzed reductive cyclization of 1,6-enynes has been developed. A sequence involving hydrogen atom transfer (HAT)/cyclization and oxygen insertion has been proposed and confirmed by isotope experiments. This benign strategy provides a viable synthetic approach to valuable carbonylated heteroaromatic compounds using ethanol as the solvent and dioxygen as the oxidant. |
| doi_str_mv | 10.1039/C8QO01190G |
| format | Article |
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A sequence involving hydrogen atom transfer (HAT)/cyclization and oxygen insertion has been proposed and confirmed by isotope experiments. This benign strategy provides a viable synthetic approach to valuable carbonylated heteroaromatic compounds using ethanol as the solvent and dioxygen as the oxidant.</description><subject>Carbonyls</subject><subject>Chemical synthesis</subject><subject>Ethanol</subject><subject>Heterocyclic compounds</subject><subject>Iron</subject><subject>Organic chemistry</subject><subject>Oxidizing agents</subject><subject>Thiophenes</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpNkE9Lw0AQxRdRsNRe_AQBb2J0dpPdZI9StC0UiqDnMNk_NCXutruJkH56Uyvo6T1mfjMPHiG3FB4pZPJpXr5tgFIJiwsyYcBZmlMmL__5azKLcQcAlHEBvJiQwyp4lyrssB2ORifB6F51zZdJ1KDa5ohd4904RfVjvE3og0iNG5yJifUh6bYmiYMbJTbxtM9SVENbG3f0tg_oYoJOj1jj91szXt2QK4ttNLNfnZKP15f3-TJdbxar-fM6VRnjXVoIjmC40LosawRb1DbXIATTOZMoDc9FUdoSmYRa5TXKLC-wzktLFYiC62xK7s5_98EfehO7auf74MbIitGCUUFBliN1f6ZU8DEGY6t9aD4xDBWF6tRq9ddq9g0AQWqw</recordid><startdate>20190207</startdate><enddate>20190207</enddate><creator>Xia, Xiao-Feng</creator><creator>He, Wei</creator><creator>Zhang, Guo-Wei</creator><creator>Wang, Dawei</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0001-9327-7487</orcidid><orcidid>https://orcid.org/0000-0002-1837-0638</orcidid></search><sort><creationdate>20190207</creationdate><title>Iron-catalyzed reductive cyclization reaction of 1,6-enynes for the synthesis of 3-acylbenzofurans and thiophenes</title><author>Xia, Xiao-Feng ; He, Wei ; Zhang, Guo-Wei ; Wang, Dawei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c325t-765a0e56dd88ba0f7bf4d0662d429a9e54678f8a290bc4ba9347ab48f1c0675d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Carbonyls</topic><topic>Chemical synthesis</topic><topic>Ethanol</topic><topic>Heterocyclic compounds</topic><topic>Iron</topic><topic>Organic chemistry</topic><topic>Oxidizing agents</topic><topic>Thiophenes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xia, Xiao-Feng</creatorcontrib><creatorcontrib>He, Wei</creatorcontrib><creatorcontrib>Zhang, Guo-Wei</creatorcontrib><creatorcontrib>Wang, Dawei</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xia, Xiao-Feng</au><au>He, Wei</au><au>Zhang, Guo-Wei</au><au>Wang, Dawei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Iron-catalyzed reductive cyclization reaction of 1,6-enynes for the synthesis of 3-acylbenzofurans and thiophenes</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2019-02-07</date><risdate>2019</risdate><volume>6</volume><issue>3</issue><spage>342</spage><epage>346</epage><pages>342-346</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>A facile synthesis of 3-acylbenzofurans and thiophenes via iron( ii )-catalyzed reductive cyclization of 1,6-enynes has been developed. A sequence involving hydrogen atom transfer (HAT)/cyclization and oxygen insertion has been proposed and confirmed by isotope experiments. This benign strategy provides a viable synthetic approach to valuable carbonylated heteroaromatic compounds using ethanol as the solvent and dioxygen as the oxidant.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/C8QO01190G</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-9327-7487</orcidid><orcidid>https://orcid.org/0000-0002-1837-0638</orcidid></addata></record> |
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| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2019-02, Vol.6 (3), p.342-346 |
| issn | 2052-4129 2052-4110 2052-4129 2052-4110 |
| language | eng |
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| source | Royal Society Of Chemistry Journals |
| subjects | Carbonyls Chemical synthesis Ethanol Heterocyclic compounds Iron Organic chemistry Oxidizing agents Thiophenes |
| title | Iron-catalyzed reductive cyclization reaction of 1,6-enynes for the synthesis of 3-acylbenzofurans and thiophenes |
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