Iron-Catalyzed N‑Arylsulfonamide Formation through Directly Using Nitroarenes as Nitrogen Sources
One-step, catalytic synthesis of N-arylsulfonamides via the construction of N–S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitr...
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| Veröffentlicht in: | Journal of organic chemistry 2015-04, Vol.80 (7), p.3504-3511 |
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| container_issue | 7 |
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| container_title | Journal of organic chemistry |
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| creator | Zhang, Weixi Xie, Junyao Rao, Bin Luo, Meiming |
| description | One-step, catalytic synthesis of N-arylsulfonamides via the construction of N–S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N–S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed. |
| doi_str_mv | 10.1021/acs.joc.5b00130 |
| format | Article |
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In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N–S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.5b00130</identifier><identifier>PMID: 25742395</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Catalysis ; Iron - chemistry ; Molecular Structure ; Nitro Compounds - chemistry ; Nitrogen - chemistry ; Sulfonamides - chemical synthesis ; Sulfonamides - chemistry</subject><ispartof>Journal of organic chemistry, 2015-04, Vol.80 (7), p.3504-3511</ispartof><rights>Copyright © 2015 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-3da3e25fffd02c7bb71fbae30a6a1e4627b34adaea229e9c28da1d6e9dbc18e93</citedby><cites>FETCH-LOGICAL-a333t-3da3e25fffd02c7bb71fbae30a6a1e4627b34adaea229e9c28da1d6e9dbc18e93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.5b00130$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.5b00130$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25742395$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Weixi</creatorcontrib><creatorcontrib>Xie, Junyao</creatorcontrib><creatorcontrib>Rao, Bin</creatorcontrib><creatorcontrib>Luo, Meiming</creatorcontrib><title>Iron-Catalyzed N‑Arylsulfonamide Formation through Directly Using Nitroarenes as Nitrogen Sources</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>One-step, catalytic synthesis of N-arylsulfonamides via the construction of N–S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N–S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.</description><subject>Catalysis</subject><subject>Iron - chemistry</subject><subject>Molecular Structure</subject><subject>Nitro Compounds - chemistry</subject><subject>Nitrogen - chemistry</subject><subject>Sulfonamides - chemical synthesis</subject><subject>Sulfonamides - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kE1Lw0AQhhdRbK2evUmOgqTdj2zSHEu1Wij1oD2Hye6kTUmydTc5xJN_wb_oLzGS6s25DAPP-8I8hFwzOmaUswkoN94bNZYppUzQEzJkklM_jGlwSoaUcu4LHooBuXBuT7uRUp6TAZdRwEUsh0Qtran8OdRQtO-ovfXXx-fMtoVrisxUUOYavYWxJdS5qbx6Z02z3Xn3uUVVF623cXm19dZ5bQ1YrNB54Ppzi5X3Yhqr0F2SswwKh1fHPSKbxcPr_MlfPT8u57OVD0KI2hcaBHKZZZmmXEVpGrEsBRQUQmAYhDxKRQAaEDiPMVZ8qoHpEGOdKjbFWIzIbd97sOatQVcnZe4UFgVUaBqXsDBinMkpFx066VFljXMWs-Rg8xJsmzCa_JhNOrNJZzY5mu0SN8fyJi1R__G_Kjvgrgf6ZGOr7td_674BQSSHiw</recordid><startdate>20150403</startdate><enddate>20150403</enddate><creator>Zhang, Weixi</creator><creator>Xie, Junyao</creator><creator>Rao, Bin</creator><creator>Luo, Meiming</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20150403</creationdate><title>Iron-Catalyzed N‑Arylsulfonamide Formation through Directly Using Nitroarenes as Nitrogen Sources</title><author>Zhang, Weixi ; Xie, Junyao ; Rao, Bin ; Luo, Meiming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-3da3e25fffd02c7bb71fbae30a6a1e4627b34adaea229e9c28da1d6e9dbc18e93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Catalysis</topic><topic>Iron - chemistry</topic><topic>Molecular Structure</topic><topic>Nitro Compounds - chemistry</topic><topic>Nitrogen - chemistry</topic><topic>Sulfonamides - chemical synthesis</topic><topic>Sulfonamides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Weixi</creatorcontrib><creatorcontrib>Xie, Junyao</creatorcontrib><creatorcontrib>Rao, Bin</creatorcontrib><creatorcontrib>Luo, Meiming</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Weixi</au><au>Xie, Junyao</au><au>Rao, Bin</au><au>Luo, Meiming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Iron-Catalyzed N‑Arylsulfonamide Formation through Directly Using Nitroarenes as Nitrogen Sources</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2015-04-03</date><risdate>2015</risdate><volume>80</volume><issue>7</issue><spage>3504</spage><epage>3511</epage><pages>3504-3511</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>One-step, catalytic synthesis of N-arylsulfonamides via the construction of N–S bonds from the direct coupling of sodium arylsulfinates with nitroarenes was realized in the presence of FeCl2 and NaHSO3 under mild conditions. In this process, stable and readily available nitroarenes were used as nitrogen sources, and NaHSO3 acted as a reductant to provide N-arylsulfonamides in good to excellent yields. A broad range of functional groups were very well-tolerated in this reaction system. In addition, mechanistic studies indicated that the N–S bond might be generated through direct coupling of nitroarene with sodium arylsulfinate prior to the reduction of nitroarenes by NaHSO3. Accordingly, a reaction mechanism involving N-aryl-N-arenesulfonylhydroxylamine as an intermediate was proposed.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25742395</pmid><doi>10.1021/acs.joc.5b00130</doi><tpages>8</tpages></addata></record> |
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| source | MEDLINE; American Chemical Society Publications |
| subjects | Catalysis Iron - chemistry Molecular Structure Nitro Compounds - chemistry Nitrogen - chemistry Sulfonamides - chemical synthesis Sulfonamides - chemistry |
| title | Iron-Catalyzed N‑Arylsulfonamide Formation through Directly Using Nitroarenes as Nitrogen Sources |
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