The Fe(iii)-catalyzed decarboxylative cycloaddition of β-ketoacids and 2H-azirines for the synthesis of pyrrole derivatives
An Fe(iii)-catalyzed Mannich/decarboxylative ring-expansion reaction for the synthesis of pyrrole derivatives is reported. β-Ketoacids were employed as enolate equivalents of a simple ketone and were coupled with 2H-azirine in a formal [3 + 2] cycloaddition reaction. A series of di-, tri-alkyl/aryl-...
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| Veröffentlicht in: | Organic chemistry frontiers an international journal of organic chemistry 2020-11, Vol.7 (22), p.3686-3691 |
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| container_title | Organic chemistry frontiers an international journal of organic chemistry |
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| creator | Hu, Haipeng Wang, Cuilin Lai, Han Wang, Siyuan Ni, Hailiang Yu, Wenhao Cao, Peng |
| description | An Fe(iii)-catalyzed Mannich/decarboxylative ring-expansion reaction for the synthesis of pyrrole derivatives is reported. β-Ketoacids were employed as enolate equivalents of a simple ketone and were coupled with 2H-azirine in a formal [3 + 2] cycloaddition reaction. A series of di-, tri-alkyl/aryl-substituted and fused pyrrole derivatives was obtained in moderate to excellent yields (17–92%) under mild reaction conditions. The products could be synthesized on gram-scale with 5 mol% catalyst loading. |
| doi_str_mv | 10.1039/d0qo00951b |
| format | Article |
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A series of di-, tri-alkyl/aryl-substituted and fused pyrrole derivatives was obtained in moderate to excellent yields (17–92%) under mild reaction conditions. 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A series of di-, tri-alkyl/aryl-substituted and fused pyrrole derivatives was obtained in moderate to excellent yields (17–92%) under mild reaction conditions. The products could be synthesized on gram-scale with 5 mol% catalyst loading.</description><subject>Aromatic compounds</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Crystallography</subject><subject>Cycloaddition</subject><subject>Derivatives</subject><subject>Iron</subject><subject>Organic chemistry</subject><issn>2052-4110</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpNjctKAzEYhYMoWGo3PkHAjS6i-ZNJZrKUYq1QcNN9SXPB1GHSJmlxik_lg_hMjpeFi8N3Nuc7CF0CvQXK1Z2lu0ipErA-QSNGBSMVAD3918_RJOcNpRSYkFTUI_S-fHF45q5DCDfE6KLb_ugsts7otI5vfatLODhsetNGbW0oIXY4evz5QV5didoEm7HuLGZzoo8hhc5l7GPCZfDmvhuQQ_5ebPuUYusGdQqHH2u-QGdet9lN_jhGy9nDcjoni-fHp-n9gmwBeCFerYVUrGbApPHAhkjvvWUKuK2VlsZ6KUGI2jWcS-0VeGNkVVHbMA18jK5-tdsUd3uXy2oT96kbHlesEo2qKykb_gV0j2IR</recordid><startdate>20201121</startdate><enddate>20201121</enddate><creator>Hu, Haipeng</creator><creator>Wang, Cuilin</creator><creator>Lai, Han</creator><creator>Wang, Siyuan</creator><creator>Ni, Hailiang</creator><creator>Yu, Wenhao</creator><creator>Cao, Peng</creator><general>Royal Society of Chemistry</general><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope></search><sort><creationdate>20201121</creationdate><title>The Fe(iii)-catalyzed decarboxylative cycloaddition of β-ketoacids and 2H-azirines for the synthesis of pyrrole derivatives</title><author>Hu, Haipeng ; Wang, Cuilin ; Lai, Han ; Wang, Siyuan ; Ni, Hailiang ; Yu, Wenhao ; Cao, Peng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p113t-f9b569272126cf12cf16fffd2913d79a6cdf661557e8336af91fcc6440d82a13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aromatic compounds</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>Crystallography</topic><topic>Cycloaddition</topic><topic>Derivatives</topic><topic>Iron</topic><topic>Organic chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hu, Haipeng</creatorcontrib><creatorcontrib>Wang, Cuilin</creatorcontrib><creatorcontrib>Lai, Han</creatorcontrib><creatorcontrib>Wang, Siyuan</creatorcontrib><creatorcontrib>Ni, Hailiang</creatorcontrib><creatorcontrib>Yu, Wenhao</creatorcontrib><creatorcontrib>Cao, Peng</creatorcontrib><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 an international journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hu, Haipeng</au><au>Wang, Cuilin</au><au>Lai, Han</au><au>Wang, Siyuan</au><au>Ni, Hailiang</au><au>Yu, Wenhao</au><au>Cao, Peng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The Fe(iii)-catalyzed decarboxylative cycloaddition of β-ketoacids and 2H-azirines for the synthesis of pyrrole derivatives</atitle><jtitle>Organic chemistry frontiers an international journal of organic chemistry</jtitle><date>2020-11-21</date><risdate>2020</risdate><volume>7</volume><issue>22</issue><spage>3686</spage><epage>3691</epage><pages>3686-3691</pages><issn>2052-4110</issn><eissn>2052-4110</eissn><abstract>An Fe(iii)-catalyzed Mannich/decarboxylative ring-expansion reaction for the synthesis of pyrrole derivatives is reported. β-Ketoacids were employed as enolate equivalents of a simple ketone and were coupled with 2H-azirine in a formal [3 + 2] cycloaddition reaction. 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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Aromatic compounds Catalysts Chemical synthesis Crystallography Cycloaddition Derivatives Iron Organic chemistry |
| title | The Fe(iii)-catalyzed decarboxylative cycloaddition of β-ketoacids and 2H-azirines for the synthesis of pyrrole derivatives |
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