Visible-light-mediated defluorinative cyclization of α-fluoro-β-enamino esters catalyzed by 4-CzIPN
Using 4-CzIPN as an energy transfer (EnT) photocatalyst and α-fluoro-β-enamino esters as substrates, a mild 6π-photocyclization/defluorination of N -aryl enamines was carried out to efficiently construct indoles without an oxidant and a transition metal catalyst under visible light irradiation. Mech...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2022-06, Vol.9 (13), p.3499-3505 |
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| container_issue | 13 |
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| container_title | Organic Chemistry Frontiers |
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| creator | Song, Yi-Fan Niu, Xiaoying Zhao, Jincan Shen, Shigang Yang, Xiu-Long |
| description | Using 4-CzIPN as an energy transfer (EnT) photocatalyst and α-fluoro-β-enamino esters as substrates, a mild 6π-photocyclization/defluorination of
N
-aryl enamines was carried out to efficiently construct indoles without an oxidant and a transition metal catalyst under visible light irradiation. Mechanistic studies reveal that the triplet
N
-aryl enamines produced through energy transfer from the excited 4-CzIPN* are responsible for the formation of indoles. |
| doi_str_mv | 10.1039/D2QO00412G |
| format | Article |
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-aryl enamines was carried out to efficiently construct indoles without an oxidant and a transition metal catalyst under visible light irradiation. Mechanistic studies reveal that the triplet
N
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N
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N
-aryl enamines produced through energy transfer from the excited 4-CzIPN* are responsible for the formation of indoles.</description><subject>Aromatic compounds</subject><subject>Catalysts</subject><subject>Defluorination</subject><subject>Energy transfer</subject><subject>Esters</subject><subject>Indoles</subject><subject>Irradiation</subject><subject>Light irradiation</subject><subject>Organic chemistry</subject><subject>Oxidants</subject><subject>Oxidizing agents</subject><subject>Substrates</subject><subject>Transition metals</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpNkM1KAzEUhYMoWGo3PsGAOyGa32mzlKq1UKyCuh2SzI2mTCc1mRamb6UP0mdytIKuzgfncO7lIHRKyQUlXF1es8c5IYKyyQHqMSIZ7lgd_uNjNEhpQQihTOZEDnsIXnzypgJc-de3Bi-h9LqBMivBVesQfa0bv4HMtrby245DnQWX7T7wjx3w7hNDrZe-DhmkBmLKrG501W67DtNmAo-304f7E3TkdJVg8Kt99Hx78zS-w7P5ZDq-mmHLRrTBVBpeGieFVJo4yVWuOClBaG6E5cByVqohOGIZGZpcMMEkk1pbrUBTQyXvo7N97yqG93X3ULEI61h3JwuWjyjP6UioLnW-T9kYUorgilX0Sx3bgpLie8nib0n-BWKSZzA</recordid><startdate>20220628</startdate><enddate>20220628</enddate><creator>Song, Yi-Fan</creator><creator>Niu, Xiaoying</creator><creator>Zhao, Jincan</creator><creator>Shen, Shigang</creator><creator>Yang, Xiu-Long</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/0000-0003-3933-7738</orcidid><orcidid>https://orcid.org/0000-0001-9128-4616</orcidid></search><sort><creationdate>20220628</creationdate><title>Visible-light-mediated defluorinative cyclization of α-fluoro-β-enamino esters catalyzed by 4-CzIPN</title><author>Song, Yi-Fan ; Niu, Xiaoying ; Zhao, Jincan ; Shen, Shigang ; Yang, Xiu-Long</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-15b3dbf5459a0f5396930de4a3b4c3e262d97ef0c207b64242525aaca9ea1b153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Aromatic compounds</topic><topic>Catalysts</topic><topic>Defluorination</topic><topic>Energy transfer</topic><topic>Esters</topic><topic>Indoles</topic><topic>Irradiation</topic><topic>Light irradiation</topic><topic>Organic chemistry</topic><topic>Oxidants</topic><topic>Oxidizing agents</topic><topic>Substrates</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Song, Yi-Fan</creatorcontrib><creatorcontrib>Niu, Xiaoying</creatorcontrib><creatorcontrib>Zhao, Jincan</creatorcontrib><creatorcontrib>Shen, Shigang</creatorcontrib><creatorcontrib>Yang, Xiu-Long</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>Song, Yi-Fan</au><au>Niu, Xiaoying</au><au>Zhao, Jincan</au><au>Shen, Shigang</au><au>Yang, Xiu-Long</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Visible-light-mediated defluorinative cyclization of α-fluoro-β-enamino esters catalyzed by 4-CzIPN</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2022-06-28</date><risdate>2022</risdate><volume>9</volume><issue>13</issue><spage>3499</spage><epage>3505</epage><pages>3499-3505</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>Using 4-CzIPN as an energy transfer (EnT) photocatalyst and α-fluoro-β-enamino esters as substrates, a mild 6π-photocyclization/defluorination of
N
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N
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| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2022-06, Vol.9 (13), p.3499-3505 |
| issn | 2052-4129 2052-4110 2052-4129 2052-4110 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Aromatic compounds Catalysts Defluorination Energy transfer Esters Indoles Irradiation Light irradiation Organic chemistry Oxidants Oxidizing agents Substrates Transition metals |
| title | Visible-light-mediated defluorinative cyclization of α-fluoro-β-enamino esters catalyzed by 4-CzIPN |
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