A covalent organic framework-catalyzed visible-light-induced three-component cascade synthesis of trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1)-one derivatives
Herein, we report a visible-light-induced three-component cascade reaction of alkenes or alkynes with CF 3 SO 2 Na and quinoxalin-2(1 H )-one derivatives. In this reaction, a photoactive two-dimensional imine-linked covalent organic framework (2D-COF-5) was employed as the heterogeneous photocatalys...
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| Veröffentlicht in: | New journal of chemistry 2022-10, Vol.46 (42), p.2412-2418 |
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| container_title | New journal of chemistry |
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| creator | Wang, Hesheng Li, Siyu Cui, Yue Liu, Minqiang Bu, Xiubin Tian, Hua Yang, Xiaobo |
| description | Herein, we report a visible-light-induced three-component cascade reaction of alkenes or alkynes with CF
3
SO
2
Na and quinoxalin-2(1
H
)-one derivatives. In this reaction, a photoactive two-dimensional imine-linked covalent organic framework (2D-COF-5) was employed as the heterogeneous photocatalyst. Benefiting from the excellent photoactivity, stability, and inherent heterogeneous nature of 2D-COF-5, this visible-light-induced three-component cascade reaction occurred smoothly in a selective, green, and sustainable manner. A wide range of C3 trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1
H
)-one derivatives were produced in satisfying yields. A preliminary investigation of the reusability for 2D-COF-5 demonstrated the good maintenance of photocatalytic performance, basic chemical structure, and micro-appearance in eight recycling runs.
A COF-catalyzed visible-light-induced three-component synthesis of trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1
H
)-one derivatives features robust substrate adaptability, good sustainability, and
Z
-selectivity. |
| doi_str_mv | 10.1039/d2nj04430g |
| format | Article |
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3
SO
2
Na and quinoxalin-2(1
H
)-one derivatives. In this reaction, a photoactive two-dimensional imine-linked covalent organic framework (2D-COF-5) was employed as the heterogeneous photocatalyst. Benefiting from the excellent photoactivity, stability, and inherent heterogeneous nature of 2D-COF-5, this visible-light-induced three-component cascade reaction occurred smoothly in a selective, green, and sustainable manner. A wide range of C3 trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1
H
)-one derivatives were produced in satisfying yields. A preliminary investigation of the reusability for 2D-COF-5 demonstrated the good maintenance of photocatalytic performance, basic chemical structure, and micro-appearance in eight recycling runs.
A COF-catalyzed visible-light-induced three-component synthesis of trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1
H
)-one derivatives features robust substrate adaptability, good sustainability, and
Z
-selectivity.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/d2nj04430g</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Alkenes ; Alkynes ; Cascade chemical reactions ; Chemical synthesis ; Photocatalysis</subject><ispartof>New journal of chemistry, 2022-10, Vol.46 (42), p.2412-2418</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-55666575727354095085760bcc4776cef80063b299613e18e7581e3e969c5fab3</citedby><cites>FETCH-LOGICAL-c281t-55666575727354095085760bcc4776cef80063b299613e18e7581e3e969c5fab3</cites><orcidid>0000-0003-0684-8419</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Wang, Hesheng</creatorcontrib><creatorcontrib>Li, Siyu</creatorcontrib><creatorcontrib>Cui, Yue</creatorcontrib><creatorcontrib>Liu, Minqiang</creatorcontrib><creatorcontrib>Bu, Xiubin</creatorcontrib><creatorcontrib>Tian, Hua</creatorcontrib><creatorcontrib>Yang, Xiaobo</creatorcontrib><title>A covalent organic framework-catalyzed visible-light-induced three-component cascade synthesis of trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1)-one derivatives</title><title>New journal of chemistry</title><description>Herein, we report a visible-light-induced three-component cascade reaction of alkenes or alkynes with CF
3
SO
2
Na and quinoxalin-2(1
H
)-one derivatives. In this reaction, a photoactive two-dimensional imine-linked covalent organic framework (2D-COF-5) was employed as the heterogeneous photocatalyst. Benefiting from the excellent photoactivity, stability, and inherent heterogeneous nature of 2D-COF-5, this visible-light-induced three-component cascade reaction occurred smoothly in a selective, green, and sustainable manner. A wide range of C3 trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1
H
)-one derivatives were produced in satisfying yields. A preliminary investigation of the reusability for 2D-COF-5 demonstrated the good maintenance of photocatalytic performance, basic chemical structure, and micro-appearance in eight recycling runs.
A COF-catalyzed visible-light-induced three-component synthesis of trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1
H
)-one derivatives features robust substrate adaptability, good sustainability, and
Z
-selectivity.</description><subject>Alkenes</subject><subject>Alkynes</subject><subject>Cascade chemical reactions</subject><subject>Chemical synthesis</subject><subject>Photocatalysis</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpVkU1LAzEURQdRUKsb90LAjQrRZDLJzCzFj6qIbnQ9pJk3bWqa1CRTrf_H_2m0orh6l8vhvMXNsj1KTihh9Wmb2ykpCkbGa9kWZaLGdS7oesq0KDDhhdjMtkOYEkJpKehW9nGGlFtIAzYi58fSaoU6L2fw6vwzVjJKs3yHFi100CMD2OjxJGJt216lNk48AFZuNnf2y6BkULIFFJY2TiDogFyHoted6Z130jwvDZK2_VeBTeVLr617k0ZbnB_SI5x0qAWvFzLqBYSdbKOTJsDuzx1kT1eXj-fX-O5heHN-dodVXtGIORdC8JKXecl4QWpOKl4KMlKqKEuhoKsIEWyU17WgDGgFJa8oMKhFrXgnR2yQHay8c-9eegixmbre2_SySUqSVzy5E3W8opR3IXjomrnXM-mXDSXN1wzNRX5_-z3DMMH7K9gH9cv9zcQ-AffEh5M</recordid><startdate>20221031</startdate><enddate>20221031</enddate><creator>Wang, Hesheng</creator><creator>Li, Siyu</creator><creator>Cui, Yue</creator><creator>Liu, Minqiang</creator><creator>Bu, Xiubin</creator><creator>Tian, Hua</creator><creator>Yang, Xiaobo</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0003-0684-8419</orcidid></search><sort><creationdate>20221031</creationdate><title>A covalent organic framework-catalyzed visible-light-induced three-component cascade synthesis of trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1)-one derivatives</title><author>Wang, Hesheng ; Li, Siyu ; Cui, Yue ; Liu, Minqiang ; Bu, Xiubin ; Tian, Hua ; Yang, Xiaobo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-55666575727354095085760bcc4776cef80063b299613e18e7581e3e969c5fab3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkenes</topic><topic>Alkynes</topic><topic>Cascade chemical reactions</topic><topic>Chemical synthesis</topic><topic>Photocatalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Hesheng</creatorcontrib><creatorcontrib>Li, Siyu</creatorcontrib><creatorcontrib>Cui, Yue</creatorcontrib><creatorcontrib>Liu, Minqiang</creatorcontrib><creatorcontrib>Bu, Xiubin</creatorcontrib><creatorcontrib>Tian, Hua</creatorcontrib><creatorcontrib>Yang, Xiaobo</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Hesheng</au><au>Li, Siyu</au><au>Cui, Yue</au><au>Liu, Minqiang</au><au>Bu, Xiubin</au><au>Tian, Hua</au><au>Yang, Xiaobo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A covalent organic framework-catalyzed visible-light-induced three-component cascade synthesis of trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1)-one derivatives</atitle><jtitle>New journal of chemistry</jtitle><date>2022-10-31</date><risdate>2022</risdate><volume>46</volume><issue>42</issue><spage>2412</spage><epage>2418</epage><pages>2412-2418</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>Herein, we report a visible-light-induced three-component cascade reaction of alkenes or alkynes with CF
3
SO
2
Na and quinoxalin-2(1
H
)-one derivatives. In this reaction, a photoactive two-dimensional imine-linked covalent organic framework (2D-COF-5) was employed as the heterogeneous photocatalyst. Benefiting from the excellent photoactivity, stability, and inherent heterogeneous nature of 2D-COF-5, this visible-light-induced three-component cascade reaction occurred smoothly in a selective, green, and sustainable manner. A wide range of C3 trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1
H
)-one derivatives were produced in satisfying yields. A preliminary investigation of the reusability for 2D-COF-5 demonstrated the good maintenance of photocatalytic performance, basic chemical structure, and micro-appearance in eight recycling runs.
A COF-catalyzed visible-light-induced three-component synthesis of trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1
H
)-one derivatives features robust substrate adaptability, good sustainability, and
Z
-selectivity.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d2nj04430g</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-0684-8419</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1144-0546 |
| ispartof | New journal of chemistry, 2022-10, Vol.46 (42), p.2412-2418 |
| issn | 1144-0546 1369-9261 |
| language | eng |
| recordid | cdi_proquest_journals_2730285572 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alkenes Alkynes Cascade chemical reactions Chemical synthesis Photocatalysis |
| title | A covalent organic framework-catalyzed visible-light-induced three-component cascade synthesis of trifluoroalkyl and trifluoroalkenyl quinoxalin-2(1)-one derivatives |
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