Copper‐Catalyzed Remote para‐C−H Functionalization of Anilines with Sodium and Lithium Sulfinates
A copper‐catalyzed, cross‐dehydrogenative coupling of anilines with sodium and lithium sulfinates was developed. By using a cooperative reaction system with Mn(OAc)3 as stoichiometric co‐oxidant a highly selective para‐functionalization of anilines was accomplished. Various functional groups were to...
Gespeichert in:
| Veröffentlicht in: | Chemistry : a European journal 2017-01, Vol.23 (1), p.96-100 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 100 |
|---|---|
| container_issue | 1 |
| container_start_page | 96 |
| container_title | Chemistry : a European journal |
| container_volume | 23 |
| creator | Liang, Shuai Bolte, Michael Manolikakes, Georg |
| description | A copper‐catalyzed, cross‐dehydrogenative coupling of anilines with sodium and lithium sulfinates was developed. By using a cooperative reaction system with Mn(OAc)3 as stoichiometric co‐oxidant a highly selective para‐functionalization of anilines was accomplished. Various functional groups were tolerated and the desired products were obtained in high yields. This method not only provides a novel approach for the synthesis of arylsulfones but might also offer new opportunities for the development of copper‐catalyzed para‐selective C−H functionalizations.
Para not ortho: A cross‐dehydrogenative coupling of anilines with sulfinic acid salts is reported. The cooperative reaction system with Cu(OAc)2 as catalyst and Mn(OAc)3 as stoichiometric co‐oxidant overrides the usual ortho‐selectivity of copper‐catalyzed directing group‐assisted C−H‐functionalizations and allows remote para‐selective C−H‐sulfonylation of anilines. |
| doi_str_mv | 10.1002/chem.201605101 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1880022561</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1835524091</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4431-a932afcafc736947ba1c546e44c6141ddfbaf3b201111d056305eec33da91baa3</originalsourceid><addsrcrecordid>eNqNkU1P3DAQhq2qqCzbXjkiS71wyWLHH9kcUQRspa2QoD1HE2dSjJI4xInQcuqxR8RP5JfU0W6pxAVGlmZsPfNqPC8hh5wtOGPxibnBZhEzrpnijH8gM65iHolEq49kxlKZRFqJdJ8ceH_LGEu1EJ_IfpwsmUqWakZ-Za7rsH_-_ZjBAPXmAUt6hY0bkHbQw_T-_OdpRc_H1gzWtVDbB5gK6ip62tratujpvR1u6LUr7dhQaEu6Dvepvh7ryrYwoP9M9iqoPX7Z5Tn5eX72I1tF68uLb9npOjJSCh5BKmKoTDiJ0GH6ArhRUqOURnPJy7IqoBJF-HCIkiktmEI0QpSQ8gJAzMnxVrfr3d2Ifsgb6w3WNbToRp_z5TKsLVaavwMVSsWSpRP69RV668Y-LGOilExkqpI4UIstZXrnfY9V3vW2gX6Tc5ZPbuWTW_mLW6HhaCc7Fg2WL_g_ewKQboF7W-PmDbk8W519_y_-F9zdo6U</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1854749572</pqid></control><display><type>article</type><title>Copper‐Catalyzed Remote para‐C−H Functionalization of Anilines with Sodium and Lithium Sulfinates</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Liang, Shuai ; Bolte, Michael ; Manolikakes, Georg</creator><creatorcontrib>Liang, Shuai ; Bolte, Michael ; Manolikakes, Georg</creatorcontrib><description>A copper‐catalyzed, cross‐dehydrogenative coupling of anilines with sodium and lithium sulfinates was developed. By using a cooperative reaction system with Mn(OAc)3 as stoichiometric co‐oxidant a highly selective para‐functionalization of anilines was accomplished. Various functional groups were tolerated and the desired products were obtained in high yields. This method not only provides a novel approach for the synthesis of arylsulfones but might also offer new opportunities for the development of copper‐catalyzed para‐selective C−H functionalizations.
Para not ortho: A cross‐dehydrogenative coupling of anilines with sulfinic acid salts is reported. The cooperative reaction system with Cu(OAc)2 as catalyst and Mn(OAc)3 as stoichiometric co‐oxidant overrides the usual ortho‐selectivity of copper‐catalyzed directing group‐assisted C−H‐functionalizations and allows remote para‐selective C−H‐sulfonylation of anilines.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201605101</identifier><identifier>PMID: 27805785</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Aniline ; Catalysts ; copper ; Coupling ; C−H functionalization ; Functional groups ; Lithium ; manganese ; site-selectivity ; Sodium ; sulfone ; Synthesis</subject><ispartof>Chemistry : a European journal, 2017-01, Vol.23 (1), p.96-100</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4431-a932afcafc736947ba1c546e44c6141ddfbaf3b201111d056305eec33da91baa3</citedby><cites>FETCH-LOGICAL-c4431-a932afcafc736947ba1c546e44c6141ddfbaf3b201111d056305eec33da91baa3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201605101$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201605101$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27805785$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liang, Shuai</creatorcontrib><creatorcontrib>Bolte, Michael</creatorcontrib><creatorcontrib>Manolikakes, Georg</creatorcontrib><title>Copper‐Catalyzed Remote para‐C−H Functionalization of Anilines with Sodium and Lithium Sulfinates</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>A copper‐catalyzed, cross‐dehydrogenative coupling of anilines with sodium and lithium sulfinates was developed. By using a cooperative reaction system with Mn(OAc)3 as stoichiometric co‐oxidant a highly selective para‐functionalization of anilines was accomplished. Various functional groups were tolerated and the desired products were obtained in high yields. This method not only provides a novel approach for the synthesis of arylsulfones but might also offer new opportunities for the development of copper‐catalyzed para‐selective C−H functionalizations.
Para not ortho: A cross‐dehydrogenative coupling of anilines with sulfinic acid salts is reported. The cooperative reaction system with Cu(OAc)2 as catalyst and Mn(OAc)3 as stoichiometric co‐oxidant overrides the usual ortho‐selectivity of copper‐catalyzed directing group‐assisted C−H‐functionalizations and allows remote para‐selective C−H‐sulfonylation of anilines.</description><subject>Aniline</subject><subject>Catalysts</subject><subject>copper</subject><subject>Coupling</subject><subject>C−H functionalization</subject><subject>Functional groups</subject><subject>Lithium</subject><subject>manganese</subject><subject>site-selectivity</subject><subject>Sodium</subject><subject>sulfone</subject><subject>Synthesis</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqNkU1P3DAQhq2qqCzbXjkiS71wyWLHH9kcUQRspa2QoD1HE2dSjJI4xInQcuqxR8RP5JfU0W6pxAVGlmZsPfNqPC8hh5wtOGPxibnBZhEzrpnijH8gM65iHolEq49kxlKZRFqJdJ8ceH_LGEu1EJ_IfpwsmUqWakZ-Za7rsH_-_ZjBAPXmAUt6hY0bkHbQw_T-_OdpRc_H1gzWtVDbB5gK6ip62tratujpvR1u6LUr7dhQaEu6Dvepvh7ryrYwoP9M9iqoPX7Z5Tn5eX72I1tF68uLb9npOjJSCh5BKmKoTDiJ0GH6ArhRUqOURnPJy7IqoBJF-HCIkiktmEI0QpSQ8gJAzMnxVrfr3d2Ifsgb6w3WNbToRp_z5TKsLVaavwMVSsWSpRP69RV668Y-LGOilExkqpI4UIstZXrnfY9V3vW2gX6Tc5ZPbuWTW_mLW6HhaCc7Fg2WL_g_ewKQboF7W-PmDbk8W519_y_-F9zdo6U</recordid><startdate>20170101</startdate><enddate>20170101</enddate><creator>Liang, Shuai</creator><creator>Bolte, Michael</creator><creator>Manolikakes, Georg</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20170101</creationdate><title>Copper‐Catalyzed Remote para‐C−H Functionalization of Anilines with Sodium and Lithium Sulfinates</title><author>Liang, Shuai ; Bolte, Michael ; Manolikakes, Georg</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4431-a932afcafc736947ba1c546e44c6141ddfbaf3b201111d056305eec33da91baa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Aniline</topic><topic>Catalysts</topic><topic>copper</topic><topic>Coupling</topic><topic>C−H functionalization</topic><topic>Functional groups</topic><topic>Lithium</topic><topic>manganese</topic><topic>site-selectivity</topic><topic>Sodium</topic><topic>sulfone</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liang, Shuai</creatorcontrib><creatorcontrib>Bolte, Michael</creatorcontrib><creatorcontrib>Manolikakes, Georg</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liang, Shuai</au><au>Bolte, Michael</au><au>Manolikakes, Georg</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper‐Catalyzed Remote para‐C−H Functionalization of Anilines with Sodium and Lithium Sulfinates</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2017-01-01</date><risdate>2017</risdate><volume>23</volume><issue>1</issue><spage>96</spage><epage>100</epage><pages>96-100</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>A copper‐catalyzed, cross‐dehydrogenative coupling of anilines with sodium and lithium sulfinates was developed. By using a cooperative reaction system with Mn(OAc)3 as stoichiometric co‐oxidant a highly selective para‐functionalization of anilines was accomplished. Various functional groups were tolerated and the desired products were obtained in high yields. This method not only provides a novel approach for the synthesis of arylsulfones but might also offer new opportunities for the development of copper‐catalyzed para‐selective C−H functionalizations.
Para not ortho: A cross‐dehydrogenative coupling of anilines with sulfinic acid salts is reported. The cooperative reaction system with Cu(OAc)2 as catalyst and Mn(OAc)3 as stoichiometric co‐oxidant overrides the usual ortho‐selectivity of copper‐catalyzed directing group‐assisted C−H‐functionalizations and allows remote para‐selective C−H‐sulfonylation of anilines.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>27805785</pmid><doi>10.1002/chem.201605101</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2017-01, Vol.23 (1), p.96-100 |
| issn | 0947-6539 1521-3765 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1880022561 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aniline Catalysts copper Coupling C−H functionalization Functional groups Lithium manganese site-selectivity Sodium sulfone Synthesis |
| title | Copper‐Catalyzed Remote para‐C−H Functionalization of Anilines with Sodium and Lithium Sulfinates |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-15T03%3A53%3A02IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Copper%E2%80%90Catalyzed%20Remote%20para%E2%80%90C%E2%88%92H%20Functionalization%20of%20Anilines%20with%20Sodium%20and%20Lithium%20Sulfinates&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Liang,%20Shuai&rft.date=2017-01-01&rft.volume=23&rft.issue=1&rft.spage=96&rft.epage=100&rft.pages=96-100&rft.issn=0947-6539&rft.eissn=1521-3765&rft.coden=CEUJED&rft_id=info:doi/10.1002/chem.201605101&rft_dat=%3Cproquest_cross%3E1835524091%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1854749572&rft_id=info:pmid/27805785&rfr_iscdi=true |