Harnessing selective PET and EnT catalysis by chlorophyll to synthesize N -alkylated quinoline-2(1 H )-ones, isoquinoline-1(2 H )-ones and 1,2,4-trioxanes
Photocatalytic syntheses of quinoline-2(1 )-ones, isoquinoline-1(2 )-ones and 1,2,4-trioxanes were achieved by selective photo-induced electron transfer (PET) and energy transfer (EnT), respectively, by chlorophyll under visible light irradiation. Quinoline-2(1 )-ones, isoquinoline-1(2 )-ones and 1,...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2021-11, Vol.19 (43), p.9433-9438 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Banu, Saira Singh, Kuldeep Tyagi, Shaifali Yadav, Anjali Yadav, Prem P |
| description | Photocatalytic syntheses of quinoline-2(1
)-ones, isoquinoline-1(2
)-ones and 1,2,4-trioxanes were achieved by selective photo-induced electron transfer (PET) and energy transfer (EnT), respectively, by chlorophyll under visible light irradiation. Quinoline-2(1
)-ones, isoquinoline-1(2
)-ones and 1,2,4-trioxanes are biologically potent scaffolds and their syntheses following mild reaction protocols are highly sought after. This work showcases the divergent photocatalytic roles of chlorophyll
., electron transfer in the case of quinolines or isoquinolines and energy transfer with allyl alcohols as substrates, affording their aerobic oxidation under green reaction conditions. The mechanistic investigations affirm that the catalytic cycle follows the electron-transfer pathway in carrying out the oxidation of
-alkyl(iso)quinolinium salts. Furthermore, the method provides an environmentally benign, simple reaction strategy for organic transformations of (N)-heterocycles. |
| doi_str_mv | 10.1039/d1ob01865e |
| format | Article |
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)-ones, isoquinoline-1(2
)-ones and 1,2,4-trioxanes were achieved by selective photo-induced electron transfer (PET) and energy transfer (EnT), respectively, by chlorophyll under visible light irradiation. Quinoline-2(1
)-ones, isoquinoline-1(2
)-ones and 1,2,4-trioxanes are biologically potent scaffolds and their syntheses following mild reaction protocols are highly sought after. This work showcases the divergent photocatalytic roles of chlorophyll
., electron transfer in the case of quinolines or isoquinolines and energy transfer with allyl alcohols as substrates, affording their aerobic oxidation under green reaction conditions. The mechanistic investigations affirm that the catalytic cycle follows the electron-transfer pathway in carrying out the oxidation of
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)-ones, isoquinoline-1(2
)-ones and 1,2,4-trioxanes were achieved by selective photo-induced electron transfer (PET) and energy transfer (EnT), respectively, by chlorophyll under visible light irradiation. Quinoline-2(1
)-ones, isoquinoline-1(2
)-ones and 1,2,4-trioxanes are biologically potent scaffolds and their syntheses following mild reaction protocols are highly sought after. This work showcases the divergent photocatalytic roles of chlorophyll
., electron transfer in the case of quinolines or isoquinolines and energy transfer with allyl alcohols as substrates, affording their aerobic oxidation under green reaction conditions. The mechanistic investigations affirm that the catalytic cycle follows the electron-transfer pathway in carrying out the oxidation of
-alkyl(iso)quinolinium salts. Furthermore, the method provides an environmentally benign, simple reaction strategy for organic transformations of (N)-heterocycles.</description><subject>Alcohols</subject><subject>Alkylation</subject><subject>Allyl alcohol</subject><subject>Catalysis</subject><subject>Chemical synthesis</subject><subject>Chlorophyll</subject><subject>Chlorophyll - analogs & derivatives</subject><subject>Chlorophyll - chemical synthesis</subject><subject>Chlorophyll - chemistry</subject><subject>Divergence</subject><subject>Electron transfer</subject><subject>Electron Transport</subject><subject>Electrons</subject><subject>Energy Transfer</subject><subject>Heterocyclic Compounds</subject><subject>Irradiation</subject><subject>Isoquinolines - chemical synthesis</subject><subject>Isoquinolines - chemistry</subject><subject>Light</subject><subject>Light irradiation</subject><subject>Molecular Structure</subject><subject>Organic compounds</subject><subject>Oxidation</subject><subject>Oxidation-Reduction</subject><subject>Photocatalysis</subject><subject>Photochemical Processes</subject><subject>Quinoline</subject><subject>Quinolines</subject><subject>Quinolines - chemical synthesis</subject><subject>Quinolines - chemistry</subject><subject>Radiation</subject><subject>Salts</subject><subject>Substrates</subject><issn>1477-0520</issn><issn>1477-0539</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkc1uFDEQhC0EIiFw4QGQJS4L2gH3-GdmjhAWFikiHJbzyD89rIN3vLFnEcOj8LSYJCwSp251faouqQh5CuwVMN69dhANg1ZJvEdOQTRNxSTv7h_3mp2QRzlfMQZdo8RDcsKFalQr4ZT8Wus0Ys5-_EozBrST_47082pD9ejoatxQqycd5uwzNTO12xBT3G_nEOgUaZ7HaYvZ_0T6iVY6fJuDntDR64MfY_AjVvUC6Jq-qGJ5sqQ-x38SLOqjdPMNlvVSVFPy8Ycut8fkwaBDxid384x8eb_anK-ri8sPH8_fXFS2FnKqjNJconEMBitQo5AtFwMzCpkF2SljOTrN1TBwi6rVRolBgR2Mc52U6PgZWdz67lNJh3nqdz5bDKGEiIfc17IVgkOjoKDP_0Ov4iGNJV2hOqmE6FRdqJe3lE0x54RDv09-p9PcA-v_NNa_g8u3N42tCvzszvJgduiO6N-K-G-2RZDT</recordid><startdate>20211110</startdate><enddate>20211110</enddate><creator>Banu, Saira</creator><creator>Singh, Kuldeep</creator><creator>Tyagi, Shaifali</creator><creator>Yadav, Anjali</creator><creator>Yadav, Prem P</creator><general>Royal Society of Chemistry</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-5387-7477</orcidid></search><sort><creationdate>20211110</creationdate><title>Harnessing selective PET and EnT catalysis by chlorophyll to synthesize N -alkylated quinoline-2(1 H )-ones, isoquinoline-1(2 H )-ones and 1,2,4-trioxanes</title><author>Banu, Saira ; 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)-ones, isoquinoline-1(2
)-ones and 1,2,4-trioxanes were achieved by selective photo-induced electron transfer (PET) and energy transfer (EnT), respectively, by chlorophyll under visible light irradiation. Quinoline-2(1
)-ones, isoquinoline-1(2
)-ones and 1,2,4-trioxanes are biologically potent scaffolds and their syntheses following mild reaction protocols are highly sought after. This work showcases the divergent photocatalytic roles of chlorophyll
., electron transfer in the case of quinolines or isoquinolines and energy transfer with allyl alcohols as substrates, affording their aerobic oxidation under green reaction conditions. The mechanistic investigations affirm that the catalytic cycle follows the electron-transfer pathway in carrying out the oxidation of
-alkyl(iso)quinolinium salts. Furthermore, the method provides an environmentally benign, simple reaction strategy for organic transformations of (N)-heterocycles.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>34676851</pmid><doi>10.1039/d1ob01865e</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-5387-7477</orcidid></addata></record> |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alcohols Alkylation Allyl alcohol Catalysis Chemical synthesis Chlorophyll Chlorophyll - analogs & derivatives Chlorophyll - chemical synthesis Chlorophyll - chemistry Divergence Electron transfer Electron Transport Electrons Energy Transfer Heterocyclic Compounds Irradiation Isoquinolines - chemical synthesis Isoquinolines - chemistry Light Light irradiation Molecular Structure Organic compounds Oxidation Oxidation-Reduction Photocatalysis Photochemical Processes Quinoline Quinolines Quinolines - chemical synthesis Quinolines - chemistry Radiation Salts Substrates |
| title | Harnessing selective PET and EnT catalysis by chlorophyll to synthesize N -alkylated quinoline-2(1 H )-ones, isoquinoline-1(2 H )-ones and 1,2,4-trioxanes |
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