Electrochemical Induced Regio‐ and Stereoselective Difunctionalization of Alkynes: The Synthesis of (E)‐β‐Iodovinyl Sulfones
An efficient, green, and oxidant‐free electrochemical method for alkyne difunctionalization was described. Using undivided electrochemical cell for iodosulfonylation of alkynes with commercially available iodide radical (NaI), arylsulfonyl radical (ArSO2NHNH2) sources, a variety of (E)‐β‐iodovinyl s...
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| Veröffentlicht in: | European journal of organic chemistry 2021-08, Vol.2021 (30), p.4284-4287 |
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| container_title | European journal of organic chemistry |
| container_volume | 2021 |
| creator | Zhang, Xinghua Lu, Danna Wang, Zhenwei |
| description | An efficient, green, and oxidant‐free electrochemical method for alkyne difunctionalization was described. Using undivided electrochemical cell for iodosulfonylation of alkynes with commercially available iodide radical (NaI), arylsulfonyl radical (ArSO2NHNH2) sources, a variety of (E)‐β‐iodovinyl sulfones were obtained in one‐pot with wide substrate scope, excellent regio‐ and stereoselectivity under mild and ecofriendly conditions.
An efficient method for electrochemical iodosulfonylation of alkynes was developed under oxidant‐free condition. This procedure affords valuable β‐iodovinyl sulfones with broad substrate scope, excellent regio‐ and stereoselectivity. Moreover, this facile protocol can be applied to gram‐scale synthesis of (E)‐β‐iodovinyl sulfone. |
| doi_str_mv | 10.1002/ejoc.202100505 |
| format | Article |
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An efficient method for electrochemical iodosulfonylation of alkynes was developed under oxidant‐free condition. This procedure affords valuable β‐iodovinyl sulfones with broad substrate scope, excellent regio‐ and stereoselectivity. Moreover, this facile protocol can be applied to gram‐scale synthesis of (E)‐β‐iodovinyl sulfone.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202100505</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; Difunctionalization ; Electrochemical cells ; Electrochemically catalyzed ; Iodosulfonylation ; Oxidizing agents ; Regioselectivity ; Stereoselectivity ; Substrates ; Sulfones</subject><ispartof>European journal of organic chemistry, 2021-08, Vol.2021 (30), p.4284-4287</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3175-4e080d0c1746a89677f44431f30faec56c932dab8cc8b6ee1ca9f2e6575521b43</citedby><cites>FETCH-LOGICAL-c3175-4e080d0c1746a89677f44431f30faec56c932dab8cc8b6ee1ca9f2e6575521b43</cites><orcidid>0000-0002-0151-6709</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.202100505$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202100505$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Zhang, Xinghua</creatorcontrib><creatorcontrib>Lu, Danna</creatorcontrib><creatorcontrib>Wang, Zhenwei</creatorcontrib><title>Electrochemical Induced Regio‐ and Stereoselective Difunctionalization of Alkynes: The Synthesis of (E)‐β‐Iodovinyl Sulfones</title><title>European journal of organic chemistry</title><description>An efficient, green, and oxidant‐free electrochemical method for alkyne difunctionalization was described. Using undivided electrochemical cell for iodosulfonylation of alkynes with commercially available iodide radical (NaI), arylsulfonyl radical (ArSO2NHNH2) sources, a variety of (E)‐β‐iodovinyl sulfones were obtained in one‐pot with wide substrate scope, excellent regio‐ and stereoselectivity under mild and ecofriendly conditions.
An efficient method for electrochemical iodosulfonylation of alkynes was developed under oxidant‐free condition. This procedure affords valuable β‐iodovinyl sulfones with broad substrate scope, excellent regio‐ and stereoselectivity. Moreover, this facile protocol can be applied to gram‐scale synthesis of (E)‐β‐iodovinyl sulfone.</description><subject>Alkynes</subject><subject>Difunctionalization</subject><subject>Electrochemical cells</subject><subject>Electrochemically catalyzed</subject><subject>Iodosulfonylation</subject><subject>Oxidizing agents</subject><subject>Regioselectivity</subject><subject>Stereoselectivity</subject><subject>Substrates</subject><subject>Sulfones</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkMFKw0AQhoMoWKtXzwte9JC6m002WW-lRq0UCraCt7DdzNqtaVazTSWeBF_AZ_FBfAifxA0VPXqZ-Yf5_oH5Pe-Q4B7BODiFhZG9AAduiHC05XUI5tzHjONtp0Ma-oTTu11vz9oFxpgzRjreW1qAXFVGzmGppSjQsMxrCTm6gXttvl7fkShzNFlBBcZCy-o1oHOt6tJJU4pCv4hWIKNQv3hoSrBnaDoHNGnK1Rystu3mOD1xtz4_XBma3Kx12RRoUhfKOH7f21GisHDw07ve7UU6HVz5o_HlcNAf-ZKSOPJDwAnOsSRxyETCWRyrMAwpURQrATJiktMgF7NEymTGAIgUXAXAojiKAjILadc72tx9rMxTDXaVLUxduRdsFkSM0iSIKXVUb0PJylhbgcoeK70UVZMRnLVBZ23Q2W_QzsA3hmddQPMPnaXX48Gf9xtxQ4c2</recordid><startdate>20210813</startdate><enddate>20210813</enddate><creator>Zhang, Xinghua</creator><creator>Lu, Danna</creator><creator>Wang, Zhenwei</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-0151-6709</orcidid></search><sort><creationdate>20210813</creationdate><title>Electrochemical Induced Regio‐ and Stereoselective Difunctionalization of Alkynes: The Synthesis of (E)‐β‐Iodovinyl Sulfones</title><author>Zhang, Xinghua ; Lu, Danna ; Wang, Zhenwei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3175-4e080d0c1746a89677f44431f30faec56c932dab8cc8b6ee1ca9f2e6575521b43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alkynes</topic><topic>Difunctionalization</topic><topic>Electrochemical cells</topic><topic>Electrochemically catalyzed</topic><topic>Iodosulfonylation</topic><topic>Oxidizing agents</topic><topic>Regioselectivity</topic><topic>Stereoselectivity</topic><topic>Substrates</topic><topic>Sulfones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Xinghua</creatorcontrib><creatorcontrib>Lu, Danna</creatorcontrib><creatorcontrib>Wang, Zhenwei</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Xinghua</au><au>Lu, Danna</au><au>Wang, Zhenwei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrochemical Induced Regio‐ and Stereoselective Difunctionalization of Alkynes: The Synthesis of (E)‐β‐Iodovinyl Sulfones</atitle><jtitle>European journal of organic chemistry</jtitle><date>2021-08-13</date><risdate>2021</risdate><volume>2021</volume><issue>30</issue><spage>4284</spage><epage>4287</epage><pages>4284-4287</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>An efficient, green, and oxidant‐free electrochemical method for alkyne difunctionalization was described. Using undivided electrochemical cell for iodosulfonylation of alkynes with commercially available iodide radical (NaI), arylsulfonyl radical (ArSO2NHNH2) sources, a variety of (E)‐β‐iodovinyl sulfones were obtained in one‐pot with wide substrate scope, excellent regio‐ and stereoselectivity under mild and ecofriendly conditions.
An efficient method for electrochemical iodosulfonylation of alkynes was developed under oxidant‐free condition. This procedure affords valuable β‐iodovinyl sulfones with broad substrate scope, excellent regio‐ and stereoselectivity. Moreover, this facile protocol can be applied to gram‐scale synthesis of (E)‐β‐iodovinyl sulfone.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202100505</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-0151-6709</orcidid></addata></record> |
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| ispartof | European journal of organic chemistry, 2021-08, Vol.2021 (30), p.4284-4287 |
| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkynes Difunctionalization Electrochemical cells Electrochemically catalyzed Iodosulfonylation Oxidizing agents Regioselectivity Stereoselectivity Substrates Sulfones |
| title | Electrochemical Induced Regio‐ and Stereoselective Difunctionalization of Alkynes: The Synthesis of (E)‐β‐Iodovinyl Sulfones |
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