Dehydrogenative 6π heterocyclization under visible light irradiation and mechanistic insights
A visible-light-driven oxidative 6π heterocyclization for the synthesis of structurally diverse π-conjugated polycyclic 1-aminoisoquinolines has been developed. The reaction proceeds under visible-light or sunlight, obviates the need for photocatalysts and transition-metals, and features an unusuall...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2021-07, Vol.8 (14), p.3788-3795 |
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| container_title | Organic Chemistry Frontiers |
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| creator | Zhang, Zhao Chen, Haohua Keller, Niklas Xiong, Qin Liu, Lei Lan, Yu Bein, Thomas Li, Jie |
| description | A visible-light-driven oxidative 6π heterocyclization for the synthesis of structurally diverse π-conjugated polycyclic 1-aminoisoquinolines has been developed. The reaction proceeds under visible-light or sunlight, obviates the need for photocatalysts and transition-metals, and features an unusually broad substrate scope and high efficacy. This synthetic pathway provided an easy access to highly fluorescent small molecules with high photoluminescence quantum yields. The N-heterocycles exhibit suitable optical properties for application as fluorescence quantum yield standards. DFT calculations were employed to gain insight into the mechanism and the results show that deprotonation is the rate-determining step, which can be promoted by a TFA additive. |
| doi_str_mv | 10.1039/D1QO00356A |
| format | Article |
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The reaction proceeds under visible-light or sunlight, obviates the need for photocatalysts and transition-metals, and features an unusually broad substrate scope and high efficacy. This synthetic pathway provided an easy access to highly fluorescent small molecules with high photoluminescence quantum yields. The N-heterocycles exhibit suitable optical properties for application as fluorescence quantum yield standards. 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The reaction proceeds under visible-light or sunlight, obviates the need for photocatalysts and transition-metals, and features an unusually broad substrate scope and high efficacy. This synthetic pathway provided an easy access to highly fluorescent small molecules with high photoluminescence quantum yields. The N-heterocycles exhibit suitable optical properties for application as fluorescence quantum yield standards. DFT calculations were employed to gain insight into the mechanism and the results show that deprotonation is the rate-determining step, which can be promoted by a TFA additive.</description><subject>Crystallography</subject><subject>Dehydrogenation</subject><subject>Fluorescence</subject><subject>Irradiation</subject><subject>Light irradiation</subject><subject>Metals</subject><subject>Optical properties</subject><subject>Organic chemistry</subject><subject>Photoluminescence</subject><subject>Photons</subject><subject>Radiation</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>2021</creationdate><recordtype>article</recordtype><recordid>eNpNkEtLw0AUhQdRsNRu_AUD7oTonVcey9JqFQpF0K0h82qmpJM6kxTqyn_oXzKlgq7O4d7v3gMHoWsCdwRYcT8nLysAJtLpGRpREDThhBbn__wlmsS4AQBCRQoiG6H3uakPOrRr46vO7Q1Ov79wbToTWnVQjfscpq3Hvdcm4L2LTjYGN25dd9iFUGl32lde461RdeVd7JzCzscjE6_Qha2aaCa_OkZvjw-vs6dkuVo8z6bLRNGcdAmXilCQMhdgGNdUpjQThljOcys0KM7IYKm1UohCZ4QTwrJBpc7kcGrZGN2c_u5C-9Gb2JWbtg9-iCypEJBCnqV8oG5PlAptjMHYchfctgqHkkB5rLD8q5D9AD9CZLY</recordid><startdate>20210721</startdate><enddate>20210721</enddate><creator>Zhang, Zhao</creator><creator>Chen, Haohua</creator><creator>Keller, Niklas</creator><creator>Xiong, Qin</creator><creator>Liu, Lei</creator><creator>Lan, Yu</creator><creator>Bein, Thomas</creator><creator>Li, Jie</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/0000-0002-6912-3346</orcidid><orcidid>https://orcid.org/0000-0003-1581-072X</orcidid><orcidid>https://orcid.org/0000-0002-2328-0020</orcidid></search><sort><creationdate>20210721</creationdate><title>Dehydrogenative 6π heterocyclization under visible light irradiation and mechanistic insights</title><author>Zhang, Zhao ; Chen, Haohua ; Keller, Niklas ; Xiong, Qin ; Liu, Lei ; Lan, Yu ; Bein, Thomas ; Li, Jie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-4bc120bb850e34d2b6275e1f448f5d0c4314482ffb559d7141137d71bd7bbc1f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Crystallography</topic><topic>Dehydrogenation</topic><topic>Fluorescence</topic><topic>Irradiation</topic><topic>Light irradiation</topic><topic>Metals</topic><topic>Optical properties</topic><topic>Organic chemistry</topic><topic>Photoluminescence</topic><topic>Photons</topic><topic>Radiation</topic><topic>Substrates</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Zhao</creatorcontrib><creatorcontrib>Chen, Haohua</creatorcontrib><creatorcontrib>Keller, Niklas</creatorcontrib><creatorcontrib>Xiong, Qin</creatorcontrib><creatorcontrib>Liu, Lei</creatorcontrib><creatorcontrib>Lan, Yu</creatorcontrib><creatorcontrib>Bein, Thomas</creatorcontrib><creatorcontrib>Li, Jie</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>Zhang, Zhao</au><au>Chen, Haohua</au><au>Keller, Niklas</au><au>Xiong, Qin</au><au>Liu, Lei</au><au>Lan, Yu</au><au>Bein, Thomas</au><au>Li, Jie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Dehydrogenative 6π heterocyclization under visible light irradiation and mechanistic insights</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2021-07-21</date><risdate>2021</risdate><volume>8</volume><issue>14</issue><spage>3788</spage><epage>3795</epage><pages>3788-3795</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>A visible-light-driven oxidative 6π heterocyclization for the synthesis of structurally diverse π-conjugated polycyclic 1-aminoisoquinolines has been developed. 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| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2021-07, Vol.8 (14), p.3788-3795 |
| issn | 2052-4129 2052-4110 2052-4129 2052-4110 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Crystallography Dehydrogenation Fluorescence Irradiation Light irradiation Metals Optical properties Organic chemistry Photoluminescence Photons Radiation Substrates Transition metals |
| title | Dehydrogenative 6π heterocyclization under visible light irradiation and mechanistic insights |
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