Electro-oxidation induced O-S cross-coupling of quinoxalinones with sodium sulfinates for synthesizing 2-sulfonyloxylated quinoxalines
The functionalization of quinoxalinones is synthetically and biologically appealing, however, C2 functionalized quinoxalinones is not reported via environmentally friendly approach. Herein, we disclosed C2-O sulfonylation of quinoxalinones via our developed electrochemical oxidative O-S coupling str...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2022-11, Vol.58 (88), p.12357-1236 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Shi, Shi-Hui Wei, Jian Liang, Chun-Miao Bai, Huan Zhu, Hai-Tao Zhang, Yantu Fu, Feng |
| description | The functionalization of quinoxalinones is synthetically and biologically appealing, however, C2 functionalized quinoxalinones is not reported
via
environmentally friendly approach. Herein, we disclosed C2-O sulfonylation of quinoxalinones
via
our developed electrochemical oxidative O-S coupling strategy for synthesizing 2-sulfonyloxylated quinoxalines. Applying this protocol, quinoxalin-ones and sodium sulfinates as the starting materials, a wide range of 2-sulfonyloxyl quinoxaline derivatives were obtained in moderate to good yields with good functional-group tolerance under mild conditions without additional oxidants. The utility of this methodology and the sulfonyloxyl handles was demonstrated trough gram-scale preparation and the synthesis of 2-substituted quinoxaline-based bioactive molecules, respectively.
The novel C2-O sulfonylation of quinoxalinones
via
electro-oxidation induced O-S coupling strategy under mild conditions was reported. |
| doi_str_mv | 10.1039/d2cc04524a |
| format | Article |
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via
environmentally friendly approach. Herein, we disclosed C2-O sulfonylation of quinoxalinones
via
our developed electrochemical oxidative O-S coupling strategy for synthesizing 2-sulfonyloxylated quinoxalines. Applying this protocol, quinoxalin-ones and sodium sulfinates as the starting materials, a wide range of 2-sulfonyloxyl quinoxaline derivatives were obtained in moderate to good yields with good functional-group tolerance under mild conditions without additional oxidants. The utility of this methodology and the sulfonyloxyl handles was demonstrated trough gram-scale preparation and the synthesis of 2-substituted quinoxaline-based bioactive molecules, respectively.
The novel C2-O sulfonylation of quinoxalinones
via
electro-oxidation induced O-S coupling strategy under mild conditions was reported.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d2cc04524a</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Chemical synthesis ; Coupling (molecular) ; Cross coupling ; Oxidation ; Oxidizing agents ; Quinoxalines ; Sodium</subject><ispartof>Chemical communications (Cambridge, England), 2022-11, Vol.58 (88), p.12357-1236</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c314t-12cd2a4a56e69e48c985d7b6f16644a8c5b86b9710d89792d1e9c9a4bcdf649f3</citedby><cites>FETCH-LOGICAL-c314t-12cd2a4a56e69e48c985d7b6f16644a8c5b86b9710d89792d1e9c9a4bcdf649f3</cites><orcidid>0000-0003-1200-962X ; 0000-0002-3778-1344 ; 0000-0002-7644-4578</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Shi, Shi-Hui</creatorcontrib><creatorcontrib>Wei, Jian</creatorcontrib><creatorcontrib>Liang, Chun-Miao</creatorcontrib><creatorcontrib>Bai, Huan</creatorcontrib><creatorcontrib>Zhu, Hai-Tao</creatorcontrib><creatorcontrib>Zhang, Yantu</creatorcontrib><creatorcontrib>Fu, Feng</creatorcontrib><title>Electro-oxidation induced O-S cross-coupling of quinoxalinones with sodium sulfinates for synthesizing 2-sulfonyloxylated quinoxalines</title><title>Chemical communications (Cambridge, England)</title><description>The functionalization of quinoxalinones is synthetically and biologically appealing, however, C2 functionalized quinoxalinones is not reported
via
environmentally friendly approach. Herein, we disclosed C2-O sulfonylation of quinoxalinones
via
our developed electrochemical oxidative O-S coupling strategy for synthesizing 2-sulfonyloxylated quinoxalines. Applying this protocol, quinoxalin-ones and sodium sulfinates as the starting materials, a wide range of 2-sulfonyloxyl quinoxaline derivatives were obtained in moderate to good yields with good functional-group tolerance under mild conditions without additional oxidants. The utility of this methodology and the sulfonyloxyl handles was demonstrated trough gram-scale preparation and the synthesis of 2-substituted quinoxaline-based bioactive molecules, respectively.
The novel C2-O sulfonylation of quinoxalinones
via
electro-oxidation induced O-S coupling strategy under mild conditions was reported.</description><subject>Chemical synthesis</subject><subject>Coupling (molecular)</subject><subject>Cross coupling</subject><subject>Oxidation</subject><subject>Oxidizing agents</subject><subject>Quinoxalines</subject><subject>Sodium</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpd0U1LwzAYB_AiCs7pxbsQ8CJCtEnTtDlKnS8w2EEFbyVNUpfRJVvS4uoH8HObbqJiLnn75eEh_yg6RfEVihN2LbEQMUkx4XvRCCWUwJTkr_vDOmUwS0h6GB15v4jDQGk-ij4njRKts9ButOSttgZoIzuhJJjBJyCc9R4K260abd6ArcG608ZueNhaozx41-0ceCt1twS-a2pteBuOa-uA7007V15_DC8xHG6t6Ru76Ztg5J9Kyh9HBzVvvDr5nsfRy93kuXiA09n9Y3EzhSJBpIUIC4k54SlVlCmSC5anMqtojSglhOcirXJasQzFMmcZwxIpJhgnlZA1JaxOxtHFru7K2XWnfFsutReqabhRtvMlzjBlOMFxHOj5P7qwnTOhu6BCN4iQnAZ1uVPbn3KqLldOL7nrSxSXQyTlLS6KbSQ3AZ_tsPPix_1GlnwByYmLrQ</recordid><startdate>20221103</startdate><enddate>20221103</enddate><creator>Shi, Shi-Hui</creator><creator>Wei, Jian</creator><creator>Liang, Chun-Miao</creator><creator>Bai, Huan</creator><creator>Zhu, Hai-Tao</creator><creator>Zhang, Yantu</creator><creator>Fu, Feng</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1200-962X</orcidid><orcidid>https://orcid.org/0000-0002-3778-1344</orcidid><orcidid>https://orcid.org/0000-0002-7644-4578</orcidid></search><sort><creationdate>20221103</creationdate><title>Electro-oxidation induced O-S cross-coupling of quinoxalinones with sodium sulfinates for synthesizing 2-sulfonyloxylated quinoxalines</title><author>Shi, Shi-Hui ; Wei, Jian ; Liang, Chun-Miao ; Bai, Huan ; Zhu, Hai-Tao ; Zhang, Yantu ; Fu, Feng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c314t-12cd2a4a56e69e48c985d7b6f16644a8c5b86b9710d89792d1e9c9a4bcdf649f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Chemical synthesis</topic><topic>Coupling (molecular)</topic><topic>Cross coupling</topic><topic>Oxidation</topic><topic>Oxidizing agents</topic><topic>Quinoxalines</topic><topic>Sodium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shi, Shi-Hui</creatorcontrib><creatorcontrib>Wei, Jian</creatorcontrib><creatorcontrib>Liang, Chun-Miao</creatorcontrib><creatorcontrib>Bai, Huan</creatorcontrib><creatorcontrib>Zhu, Hai-Tao</creatorcontrib><creatorcontrib>Zhang, Yantu</creatorcontrib><creatorcontrib>Fu, Feng</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shi, Shi-Hui</au><au>Wei, Jian</au><au>Liang, Chun-Miao</au><au>Bai, Huan</au><au>Zhu, Hai-Tao</au><au>Zhang, Yantu</au><au>Fu, Feng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electro-oxidation induced O-S cross-coupling of quinoxalinones with sodium sulfinates for synthesizing 2-sulfonyloxylated quinoxalines</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><date>2022-11-03</date><risdate>2022</risdate><volume>58</volume><issue>88</issue><spage>12357</spage><epage>1236</epage><pages>12357-1236</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The functionalization of quinoxalinones is synthetically and biologically appealing, however, C2 functionalized quinoxalinones is not reported
via
environmentally friendly approach. Herein, we disclosed C2-O sulfonylation of quinoxalinones
via
our developed electrochemical oxidative O-S coupling strategy for synthesizing 2-sulfonyloxylated quinoxalines. Applying this protocol, quinoxalin-ones and sodium sulfinates as the starting materials, a wide range of 2-sulfonyloxyl quinoxaline derivatives were obtained in moderate to good yields with good functional-group tolerance under mild conditions without additional oxidants. The utility of this methodology and the sulfonyloxyl handles was demonstrated trough gram-scale preparation and the synthesis of 2-substituted quinoxaline-based bioactive molecules, respectively.
The novel C2-O sulfonylation of quinoxalinones
via
electro-oxidation induced O-S coupling strategy under mild conditions was reported.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d2cc04524a</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-1200-962X</orcidid><orcidid>https://orcid.org/0000-0002-3778-1344</orcidid><orcidid>https://orcid.org/0000-0002-7644-4578</orcidid></addata></record> |
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| ispartof | Chemical communications (Cambridge, England), 2022-11, Vol.58 (88), p.12357-1236 |
| issn | 1359-7345 1364-548X |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Chemical synthesis Coupling (molecular) Cross coupling Oxidation Oxidizing agents Quinoxalines Sodium |
| title | Electro-oxidation induced O-S cross-coupling of quinoxalinones with sodium sulfinates for synthesizing 2-sulfonyloxylated quinoxalines |
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