Photocatalytic access to aromatic keto sulfonyl fluorides from vinyl fluorosulfates
We present herein an efficient photocatalytic transformation of vinyl fluorosulfates to aromatic β-keto sulfonyl fluorides with 1 mol% of iridium catalyst under the irradiation of 3 W blue LEDs. Preliminary mechanistic studies proposed a direct radical fragmentation and recombination of vinyl fluoro...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2022-06, Vol.9 (13), p.3540-3545 |
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| container_issue | 13 |
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| container_title | Organic Chemistry Frontiers |
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| creator | Cui, Jianchao Ke, Sen Zhao, Jia Wu, Shufeng Luo, Wencheng Xu, Shinuo Su, Xiaolong Li, Yi |
| description | We present herein an efficient photocatalytic transformation of vinyl fluorosulfates to aromatic β-keto sulfonyl fluorides with 1 mol% of iridium catalyst under the irradiation of 3 W blue LEDs. Preliminary mechanistic studies proposed a direct radical fragmentation and recombination of vinyl fluorosulfates through a free fluorosulfonyl radical (FSO
2
˙
). This methodology provides a facile approach to aromatic β-keto sulfonyl fluorides, featuring sustainable conditions and a broad substrate scope (32 examples) with 33%–90% isolated yields. |
| doi_str_mv | 10.1039/D2QO00416J |
| format | Article |
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2
˙
). This methodology provides a facile approach to aromatic β-keto sulfonyl fluorides, featuring sustainable conditions and a broad substrate scope (32 examples) with 33%–90% isolated yields.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D2QO00416J</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Catalysts ; Fluorides ; Iridium ; Irradiation ; Organic chemistry ; Radiation ; Recombination ; Substrates</subject><ispartof>Organic Chemistry Frontiers, 2022-06, Vol.9 (13), p.3540-3545</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-704a7590f5537492b4bb94433035fcf7222842319e5b8121d997e11db6e2ef953</citedby><cites>FETCH-LOGICAL-c281t-704a7590f5537492b4bb94433035fcf7222842319e5b8121d997e11db6e2ef953</cites><orcidid>0000-0002-4236-262X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids></links><search><creatorcontrib>Cui, Jianchao</creatorcontrib><creatorcontrib>Ke, Sen</creatorcontrib><creatorcontrib>Zhao, Jia</creatorcontrib><creatorcontrib>Wu, Shufeng</creatorcontrib><creatorcontrib>Luo, Wencheng</creatorcontrib><creatorcontrib>Xu, Shinuo</creatorcontrib><creatorcontrib>Su, Xiaolong</creatorcontrib><creatorcontrib>Li, Yi</creatorcontrib><title>Photocatalytic access to aromatic keto sulfonyl fluorides from vinyl fluorosulfates</title><title>Organic Chemistry Frontiers</title><description>We present herein an efficient photocatalytic transformation of vinyl fluorosulfates to aromatic β-keto sulfonyl fluorides with 1 mol% of iridium catalyst under the irradiation of 3 W blue LEDs. Preliminary mechanistic studies proposed a direct radical fragmentation and recombination of vinyl fluorosulfates through a free fluorosulfonyl radical (FSO
2
˙
). This methodology provides a facile approach to aromatic β-keto sulfonyl fluorides, featuring sustainable conditions and a broad substrate scope (32 examples) with 33%–90% isolated yields.</description><subject>Catalysts</subject><subject>Fluorides</subject><subject>Iridium</subject><subject>Irradiation</subject><subject>Organic chemistry</subject><subject>Radiation</subject><subject>Recombination</subject><subject>Substrates</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>eNpNkE9LAzEQxYMoWGovfoIFb8LqzCTZ3Ryl_qdQRT0v2TTBrdumJlmh394tFfU0M48f7w2PsVOECwSuLq_peQ4gsHg8YCMCSblAUof_9mM2iXEJAEiyAFmO2MvTu0_e6KS7bWpNpo2xMWbJZzr4ld5JH3a4Yt85v952met6H9qFjZkbgOyr_RX9jtHJxhN25HQX7eRnjtnb7c3r9D6fze8eplez3FCFKS9B6FIqcFLyUihqRNMoITgHLp1xJRFVgjgqK5sKCRdKlRZx0RSWrFOSj9nZ3ncT_GdvY6qXvg_rIbKmokJeoOLFQJ3vKTN8GIN19Sa0Kx22NUK9663-641_A2yVX1Q</recordid><startdate>20220628</startdate><enddate>20220628</enddate><creator>Cui, Jianchao</creator><creator>Ke, Sen</creator><creator>Zhao, Jia</creator><creator>Wu, Shufeng</creator><creator>Luo, Wencheng</creator><creator>Xu, Shinuo</creator><creator>Su, Xiaolong</creator><creator>Li, Yi</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/0000-0002-4236-262X</orcidid></search><sort><creationdate>20220628</creationdate><title>Photocatalytic access to aromatic keto sulfonyl fluorides from vinyl fluorosulfates</title><author>Cui, Jianchao ; Ke, Sen ; Zhao, Jia ; Wu, Shufeng ; Luo, Wencheng ; Xu, Shinuo ; Su, Xiaolong ; Li, Yi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-704a7590f5537492b4bb94433035fcf7222842319e5b8121d997e11db6e2ef953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Catalysts</topic><topic>Fluorides</topic><topic>Iridium</topic><topic>Irradiation</topic><topic>Organic chemistry</topic><topic>Radiation</topic><topic>Recombination</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cui, Jianchao</creatorcontrib><creatorcontrib>Ke, Sen</creatorcontrib><creatorcontrib>Zhao, Jia</creatorcontrib><creatorcontrib>Wu, Shufeng</creatorcontrib><creatorcontrib>Luo, Wencheng</creatorcontrib><creatorcontrib>Xu, Shinuo</creatorcontrib><creatorcontrib>Su, Xiaolong</creatorcontrib><creatorcontrib>Li, Yi</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>Cui, Jianchao</au><au>Ke, Sen</au><au>Zhao, Jia</au><au>Wu, Shufeng</au><au>Luo, Wencheng</au><au>Xu, Shinuo</au><au>Su, Xiaolong</au><au>Li, Yi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photocatalytic access to aromatic keto sulfonyl fluorides from vinyl fluorosulfates</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2022-06-28</date><risdate>2022</risdate><volume>9</volume><issue>13</issue><spage>3540</spage><epage>3545</epage><pages>3540-3545</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>We present herein an efficient photocatalytic transformation of vinyl fluorosulfates to aromatic β-keto sulfonyl fluorides with 1 mol% of iridium catalyst under the irradiation of 3 W blue LEDs. Preliminary mechanistic studies proposed a direct radical fragmentation and recombination of vinyl fluorosulfates through a free fluorosulfonyl radical (FSO
2
˙
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| fulltext | fulltext |
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| ispartof | Organic Chemistry Frontiers, 2022-06, Vol.9 (13), p.3540-3545 |
| issn | 2052-4129 2052-4110 2052-4129 2052-4110 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Catalysts Fluorides Iridium Irradiation Organic chemistry Radiation Recombination Substrates |
| title | Photocatalytic access to aromatic keto sulfonyl fluorides from vinyl fluorosulfates |
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