Visible-light-induced sulfonylation of Baylis-Hillman acetates under metal- and oxidant-free conditions
A metal-free and oxidant-free procedure for the sulfonylation of Baylis-Hillman acetates with sulfonyl hydrazides under the irradiation of visible light and open-air conditions at room temperature is described. This transformation has high yields (up to 92%), excellent stereoselectivity, broad subst...
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| Veröffentlicht in: | New journal of chemistry 2021-12, Vol.45 (47), p.22243-22248 |
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| container_issue | 47 |
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| container_title | New journal of chemistry |
| container_volume | 45 |
| creator | Yang, Cai-Yun Zhang, De-Run Hu, Lin-Ping Li, Xia Yang, Shi-Chen Liu, Bo Huang, Guo-Li |
| description | A metal-free and oxidant-free procedure for the sulfonylation of Baylis-Hillman acetates with sulfonyl hydrazides under the irradiation of visible light and open-air conditions at room temperature is described. This transformation has high yields (up to 92%), excellent stereoselectivity, broad substrate scope, good functional group tolerance, and mild reaction conditions. Moreover, mechanistic studies indicate that a sulfonyl radical pathway is involved in this reaction.
A visible-light-driven metal- and oxidant-free procedure for the sulfonylation of Baylis-Hillman acetates with sulfonyl hydrazides under open-air conditions at room temperature is reported. The methods provide a green and facile synthetic route to access allylic sulfones. |
| doi_str_mv | 10.1039/d1nj04878c |
| format | Article |
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A visible-light-driven metal- and oxidant-free procedure for the sulfonylation of Baylis-Hillman acetates with sulfonyl hydrazides under open-air conditions at room temperature is reported. The methods provide a green and facile synthetic route to access allylic sulfones.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/d1nj04878c</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Acetates ; Functional groups ; Hydrazides ; Oxidizing agents ; Room temperature ; Stereoselectivity ; Substrates</subject><ispartof>New journal of chemistry, 2021-12, Vol.45 (47), p.22243-22248</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-6022ef6ec2d0e88fff7f237edfcfdcc820edc760cbacacb27e53d67f6ee92d203</citedby><cites>FETCH-LOGICAL-c281t-6022ef6ec2d0e88fff7f237edfcfdcc820edc760cbacacb27e53d67f6ee92d203</cites><orcidid>0000-0002-3666-8649</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>Yang, Cai-Yun</creatorcontrib><creatorcontrib>Zhang, De-Run</creatorcontrib><creatorcontrib>Hu, Lin-Ping</creatorcontrib><creatorcontrib>Li, Xia</creatorcontrib><creatorcontrib>Yang, Shi-Chen</creatorcontrib><creatorcontrib>Liu, Bo</creatorcontrib><creatorcontrib>Huang, Guo-Li</creatorcontrib><title>Visible-light-induced sulfonylation of Baylis-Hillman acetates under metal- and oxidant-free conditions</title><title>New journal of chemistry</title><description>A metal-free and oxidant-free procedure for the sulfonylation of Baylis-Hillman acetates with sulfonyl hydrazides under the irradiation of visible light and open-air conditions at room temperature is described. This transformation has high yields (up to 92%), excellent stereoselectivity, broad substrate scope, good functional group tolerance, and mild reaction conditions. Moreover, mechanistic studies indicate that a sulfonyl radical pathway is involved in this reaction.
A visible-light-driven metal- and oxidant-free procedure for the sulfonylation of Baylis-Hillman acetates with sulfonyl hydrazides under open-air conditions at room temperature is reported. The methods provide a green and facile synthetic route to access allylic sulfones.</description><subject>Acetates</subject><subject>Functional groups</subject><subject>Hydrazides</subject><subject>Oxidizing agents</subject><subject>Room temperature</subject><subject>Stereoselectivity</subject><subject>Substrates</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpFkE1LAzEQhoMoWKsX70LAmxBNstskPWr9qFL0ol6XNJnUlDSpyS7Yf-_Wip5mBp73HXgQOmX0ktFqfGVZXNJaSWX20IBVYkzGXLD9fmd1TeioFofoqJQlpYxJwQZo8e6LnwcgwS8-WuKj7QxYXLrgUtwE3foUcXL4Rm-CL2TqQ1jpiLWBVrdQcBctZLzqr0CwjhanL291bInLANikaP22ohyjA6dDgZPfOURv93evkymZvTw8Tq5nxHDFWiIo5-AEGG4pKOWck45XEqwzzhqjOAVrpKBmro02cy5hVFkh-wSMueW0GqLzXe86p88OStssU5dj_7LhggolR0rWPXWxo0xOpWRwzTr7lc6bhtFmK7K5Zc9PPyInPXy2g3Mxf9y_6Oob3w1yyw</recordid><startdate>20211206</startdate><enddate>20211206</enddate><creator>Yang, Cai-Yun</creator><creator>Zhang, De-Run</creator><creator>Hu, Lin-Ping</creator><creator>Li, Xia</creator><creator>Yang, Shi-Chen</creator><creator>Liu, Bo</creator><creator>Huang, Guo-Li</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/0000-0002-3666-8649</orcidid></search><sort><creationdate>20211206</creationdate><title>Visible-light-induced sulfonylation of Baylis-Hillman acetates under metal- and oxidant-free conditions</title><author>Yang, Cai-Yun ; Zhang, De-Run ; Hu, Lin-Ping ; Li, Xia ; Yang, Shi-Chen ; Liu, Bo ; Huang, Guo-Li</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-6022ef6ec2d0e88fff7f237edfcfdcc820edc760cbacacb27e53d67f6ee92d203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Acetates</topic><topic>Functional groups</topic><topic>Hydrazides</topic><topic>Oxidizing agents</topic><topic>Room temperature</topic><topic>Stereoselectivity</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Cai-Yun</creatorcontrib><creatorcontrib>Zhang, De-Run</creatorcontrib><creatorcontrib>Hu, Lin-Ping</creatorcontrib><creatorcontrib>Li, Xia</creatorcontrib><creatorcontrib>Yang, Shi-Chen</creatorcontrib><creatorcontrib>Liu, Bo</creatorcontrib><creatorcontrib>Huang, Guo-Li</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>Yang, Cai-Yun</au><au>Zhang, De-Run</au><au>Hu, Lin-Ping</au><au>Li, Xia</au><au>Yang, Shi-Chen</au><au>Liu, Bo</au><au>Huang, Guo-Li</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Visible-light-induced sulfonylation of Baylis-Hillman acetates under metal- and oxidant-free conditions</atitle><jtitle>New journal of chemistry</jtitle><date>2021-12-06</date><risdate>2021</risdate><volume>45</volume><issue>47</issue><spage>22243</spage><epage>22248</epage><pages>22243-22248</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>A metal-free and oxidant-free procedure for the sulfonylation of Baylis-Hillman acetates with sulfonyl hydrazides under the irradiation of visible light and open-air conditions at room temperature is described. This transformation has high yields (up to 92%), excellent stereoselectivity, broad substrate scope, good functional group tolerance, and mild reaction conditions. Moreover, mechanistic studies indicate that a sulfonyl radical pathway is involved in this reaction.
A visible-light-driven metal- and oxidant-free procedure for the sulfonylation of Baylis-Hillman acetates with sulfonyl hydrazides under open-air conditions at room temperature is reported. The methods provide a green and facile synthetic route to access allylic sulfones.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1nj04878c</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-3666-8649</orcidid></addata></record> |
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| ispartof | New journal of chemistry, 2021-12, Vol.45 (47), p.22243-22248 |
| issn | 1144-0546 1369-9261 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Acetates Functional groups Hydrazides Oxidizing agents Room temperature Stereoselectivity Substrates |
| title | Visible-light-induced sulfonylation of Baylis-Hillman acetates under metal- and oxidant-free conditions |
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