Visible‐Light‐Driven Remote C−H Chlorination of Aliphatic Sulfonamides with Sodium Hypochlorite
The C(sp3)−H chlorination of aliphatic sulfonamides was realized by visible‐light photoredox catalysis with Ru(bpy)3Cl2 as photocatalsyt and NaOCl⋅5H2O crystals as the chlorinating agent. The reaction proceeds in a tandem pattern of N−H chlorination and Hofmann‐Löffler‐Freytag chlorination. A variet...
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| Veröffentlicht in: | Asian journal of organic chemistry 2020-10, Vol.9 (10), p.1650-1654 |
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| container_title | Asian journal of organic chemistry |
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| creator | Zhu, Yanshuo Wang, Juan‐Juan Wu, Danhua Yu, Wei |
| description | The C(sp3)−H chlorination of aliphatic sulfonamides was realized by visible‐light photoredox catalysis with Ru(bpy)3Cl2 as photocatalsyt and NaOCl⋅5H2O crystals as the chlorinating agent. The reaction proceeds in a tandem pattern of N−H chlorination and Hofmann‐Löffler‐Freytag chlorination. A variety of differently substituted sulfonamides were chlorinated in this way in high yield. A radical‐chain mechanism is proposed for the reaction on the basis of experimental evidence.
The C(sp3)−H chlorination of aliphatic sulfonamides was realized by visible light photoredox catalysis with Ru(bpy)3Cl2 as photocatalsyt and NaOCl⋅5H2O crystals as chlorinating agent. The reaction proceeds in a tandem pattern of N−H chlorination and Hofmann‐Löffler‐Freytag chlorination. A variety of differently substituted sulfonamides were chlorinated in this way in high yield. A radical chain mechanism is proposed for the reaction on the basis of experimental evidence. |
| doi_str_mv | 10.1002/ajoc.202000354 |
| format | Article |
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The C(sp3)−H chlorination of aliphatic sulfonamides was realized by visible light photoredox catalysis with Ru(bpy)3Cl2 as photocatalsyt and NaOCl⋅5H2O crystals as chlorinating agent. The reaction proceeds in a tandem pattern of N−H chlorination and Hofmann‐Löffler‐Freytag chlorination. A variety of differently substituted sulfonamides were chlorinated in this way in high yield. A radical chain mechanism is proposed for the reaction on the basis of experimental evidence.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.202000354</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Aliphatic compounds ; Chlorination ; C−H activation ; hydrogen atom transfer ; Organic chemistry ; photocatalysis ; Photoredox catalysis ; Sodium hypochlorite ; Sulfonamides</subject><ispartof>Asian journal of organic chemistry, 2020-10, Vol.9 (10), p.1650-1654</ispartof><rights>2020 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3174-50b6ef68540e6c8e5c6a352ceab755aad2512c1628712929401a1c876e69cfa53</citedby><cites>FETCH-LOGICAL-c3174-50b6ef68540e6c8e5c6a352ceab755aad2512c1628712929401a1c876e69cfa53</cites><orcidid>0000-0002-3131-3080</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%2Fajoc.202000354$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.202000354$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Zhu, Yanshuo</creatorcontrib><creatorcontrib>Wang, Juan‐Juan</creatorcontrib><creatorcontrib>Wu, Danhua</creatorcontrib><creatorcontrib>Yu, Wei</creatorcontrib><title>Visible‐Light‐Driven Remote C−H Chlorination of Aliphatic Sulfonamides with Sodium Hypochlorite</title><title>Asian journal of organic chemistry</title><description>The C(sp3)−H chlorination of aliphatic sulfonamides was realized by visible‐light photoredox catalysis with Ru(bpy)3Cl2 as photocatalsyt and NaOCl⋅5H2O crystals as the chlorinating agent. The reaction proceeds in a tandem pattern of N−H chlorination and Hofmann‐Löffler‐Freytag chlorination. A variety of differently substituted sulfonamides were chlorinated in this way in high yield. A radical‐chain mechanism is proposed for the reaction on the basis of experimental evidence.
The C(sp3)−H chlorination of aliphatic sulfonamides was realized by visible light photoredox catalysis with Ru(bpy)3Cl2 as photocatalsyt and NaOCl⋅5H2O crystals as chlorinating agent. The reaction proceeds in a tandem pattern of N−H chlorination and Hofmann‐Löffler‐Freytag chlorination. A variety of differently substituted sulfonamides were chlorinated in this way in high yield. A radical chain mechanism is proposed for the reaction on the basis of experimental evidence.</description><subject>Aliphatic compounds</subject><subject>Chlorination</subject><subject>C−H activation</subject><subject>hydrogen atom transfer</subject><subject>Organic chemistry</subject><subject>photocatalysis</subject><subject>Photoredox catalysis</subject><subject>Sodium hypochlorite</subject><subject>Sulfonamides</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkD1PwzAQhi0EElXpymyJOcV24nyMVfgoqFIlCqyW616IqyQOdkKVjZER8RP7S0gpKiPT3UnPc3d6ETqnZEwJYZdybdSYEUYI8XlwhAaMJr7HY8qPDz2JTtHIuXXPkChKKEsGCJ6108sCtu-fM_2SN329svoNKvwApWkAp9uPrylO88JYXclGmwqbDE8KXef9pPCiLTJTyVKvwOGNbnK8MCvdlnja1Ub9aA2coZNMFg5Gv3WInm6uH9OpN5vf3qWTmad8GgUeJ8sQsjDmAYFQxcBVKH3OFMhlxLmUK8YpUzRkcdQ_z5KAUElVHIUQJiqT3B-ii_3e2prXFlwj1qa1VX9SsCBIAsZ9uqPGe0pZ45yFTNRWl9J2ghKxS1Ps0hSHNHsh2QsbXUD3Dy0m9_P0z_0GLjZ7jQ</recordid><startdate>202010</startdate><enddate>202010</enddate><creator>Zhu, Yanshuo</creator><creator>Wang, Juan‐Juan</creator><creator>Wu, Danhua</creator><creator>Yu, Wei</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-3131-3080</orcidid></search><sort><creationdate>202010</creationdate><title>Visible‐Light‐Driven Remote C−H Chlorination of Aliphatic Sulfonamides with Sodium Hypochlorite</title><author>Zhu, Yanshuo ; Wang, Juan‐Juan ; Wu, Danhua ; Yu, Wei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3174-50b6ef68540e6c8e5c6a352ceab755aad2512c1628712929401a1c876e69cfa53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aliphatic compounds</topic><topic>Chlorination</topic><topic>C−H activation</topic><topic>hydrogen atom transfer</topic><topic>Organic chemistry</topic><topic>photocatalysis</topic><topic>Photoredox catalysis</topic><topic>Sodium hypochlorite</topic><topic>Sulfonamides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhu, Yanshuo</creatorcontrib><creatorcontrib>Wang, Juan‐Juan</creatorcontrib><creatorcontrib>Wu, Danhua</creatorcontrib><creatorcontrib>Yu, Wei</creatorcontrib><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhu, Yanshuo</au><au>Wang, Juan‐Juan</au><au>Wu, Danhua</au><au>Yu, Wei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Visible‐Light‐Driven Remote C−H Chlorination of Aliphatic Sulfonamides with Sodium Hypochlorite</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2020-10</date><risdate>2020</risdate><volume>9</volume><issue>10</issue><spage>1650</spage><epage>1654</epage><pages>1650-1654</pages><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>The C(sp3)−H chlorination of aliphatic sulfonamides was realized by visible‐light photoredox catalysis with Ru(bpy)3Cl2 as photocatalsyt and NaOCl⋅5H2O crystals as the chlorinating agent. The reaction proceeds in a tandem pattern of N−H chlorination and Hofmann‐Löffler‐Freytag chlorination. A variety of differently substituted sulfonamides were chlorinated in this way in high yield. A radical‐chain mechanism is proposed for the reaction on the basis of experimental evidence.
The C(sp3)−H chlorination of aliphatic sulfonamides was realized by visible light photoredox catalysis with Ru(bpy)3Cl2 as photocatalsyt and NaOCl⋅5H2O crystals as chlorinating agent. The reaction proceeds in a tandem pattern of N−H chlorination and Hofmann‐Löffler‐Freytag chlorination. A variety of differently substituted sulfonamides were chlorinated in this way in high yield. A radical chain mechanism is proposed for the reaction on the basis of experimental evidence.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ajoc.202000354</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-3131-3080</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aliphatic compounds Chlorination C−H activation hydrogen atom transfer Organic chemistry photocatalysis Photoredox catalysis Sodium hypochlorite Sulfonamides |
| title | Visible‐Light‐Driven Remote C−H Chlorination of Aliphatic Sulfonamides with Sodium Hypochlorite |
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