Oxidative Radical Arylation of Anilines with Arylhydrazines and Dioxygen from Air
Substituted 2-aminobiphenyls have been prepared from arylhydrazine hydrochlorides and anilines in biphasic radical arylation reactions with dioxygen from air as a most simple and readily available oxidant. Under optimized conditions, the free amino functionality of the aniline leads to high ortho:me...
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| Veröffentlicht in: | Journal of organic chemistry 2014-03, Vol.79 (5), p.2314-2320 |
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| container_title | Journal of organic chemistry |
| container_volume | 79 |
| creator | Hofmann, Josefa Jasch, Hannelore Heinrich, Markus R |
| description | Substituted 2-aminobiphenyls have been prepared from arylhydrazine hydrochlorides and anilines in biphasic radical arylation reactions with dioxygen from air as a most simple and readily available oxidant. Under optimized conditions, the free amino functionality of the aniline leads to high ortho:meta regioselectivities, now even for anilines bearing a donor substituent in the para position. Finally, the mild and metal-free new access to aminobiphenyls was shown to be applicable on a gram scale. |
| doi_str_mv | 10.1021/jo500063r |
| format | Article |
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Under optimized conditions, the free amino functionality of the aniline leads to high ortho:meta regioselectivities, now even for anilines bearing a donor substituent in the para position. Finally, the mild and metal-free new access to aminobiphenyls was shown to be applicable on a gram scale.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo500063r</identifier><identifier>PMID: 24524356</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Air ; Aminobiphenyl Compounds - chemical synthesis ; Aminobiphenyl Compounds - chemistry ; Aniline Compounds - chemistry ; Catalysis ; Hydrazines - chemistry ; Molecular Structure ; Oxidation-Reduction ; Oxygen - chemistry ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2014-03, Vol.79 (5), p.2314-2320</ispartof><rights>Copyright © 2014 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-73f7cfbb2fe734b24205865c02ff20452fa84b618d479b17559bc11f5726598d3</citedby><cites>FETCH-LOGICAL-a315t-73f7cfbb2fe734b24205865c02ff20452fa84b618d479b17559bc11f5726598d3</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/jo500063r$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo500063r$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2764,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24524356$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hofmann, Josefa</creatorcontrib><creatorcontrib>Jasch, Hannelore</creatorcontrib><creatorcontrib>Heinrich, Markus R</creatorcontrib><title>Oxidative Radical Arylation of Anilines with Arylhydrazines and Dioxygen from Air</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Substituted 2-aminobiphenyls have been prepared from arylhydrazine hydrochlorides and anilines in biphasic radical arylation reactions with dioxygen from air as a most simple and readily available oxidant. Under optimized conditions, the free amino functionality of the aniline leads to high ortho:meta regioselectivities, now even for anilines bearing a donor substituent in the para position. Finally, the mild and metal-free new access to aminobiphenyls was shown to be applicable on a gram scale.</description><subject>Air</subject><subject>Aminobiphenyl Compounds - chemical synthesis</subject><subject>Aminobiphenyl Compounds - chemistry</subject><subject>Aniline Compounds - chemistry</subject><subject>Catalysis</subject><subject>Hydrazines - chemistry</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><subject>Oxygen - chemistry</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEtPwzAQhC0EoqVw4A-gXJDgEPBrneQYlaeEVIHgHDmJTV3lUewEGn49pi09cVpp9tvRziB0SvAVwZRcL1rAGAtm99CYAMWhSDDfR2OMKQ0ZFWyEjpxbeAYDwCEaUQ6UMxBj9DxbmVJ25lMFL7I0hayC1A6VV9omaHWQNqYyjXLBl-nm69V8KK38XmuyKYMb066Gd9UE2rZ1kBp7jA60rJw62c4Jeru7fZ0-hE-z-8dp-hRKRqALI6ajQuc51SpiPKecYogFFJhqTbH_T8uY54LEJY-SnEQASV4QoiGiApK4ZBN0sfFd2vajV67LauMKVVWyUW3vMgIYKBBOhEcvN2hhW-es0tnSmlraISM4-20w2zXo2bOtbZ_XqtyRf5V54HwDyML5u942PuU_Rj-UEXZi</recordid><startdate>20140307</startdate><enddate>20140307</enddate><creator>Hofmann, Josefa</creator><creator>Jasch, Hannelore</creator><creator>Heinrich, Markus R</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>20140307</creationdate><title>Oxidative Radical Arylation of Anilines with Arylhydrazines and Dioxygen from Air</title><author>Hofmann, Josefa ; Jasch, Hannelore ; Heinrich, Markus R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-73f7cfbb2fe734b24205865c02ff20452fa84b618d479b17559bc11f5726598d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Air</topic><topic>Aminobiphenyl Compounds - chemical synthesis</topic><topic>Aminobiphenyl Compounds - chemistry</topic><topic>Aniline Compounds - chemistry</topic><topic>Catalysis</topic><topic>Hydrazines - chemistry</topic><topic>Molecular Structure</topic><topic>Oxidation-Reduction</topic><topic>Oxygen - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hofmann, Josefa</creatorcontrib><creatorcontrib>Jasch, Hannelore</creatorcontrib><creatorcontrib>Heinrich, Markus R</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>Hofmann, Josefa</au><au>Jasch, Hannelore</au><au>Heinrich, Markus R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxidative Radical Arylation of Anilines with Arylhydrazines and Dioxygen from Air</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2014-03-07</date><risdate>2014</risdate><volume>79</volume><issue>5</issue><spage>2314</spage><epage>2320</epage><pages>2314-2320</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Substituted 2-aminobiphenyls have been prepared from arylhydrazine hydrochlorides and anilines in biphasic radical arylation reactions with dioxygen from air as a most simple and readily available oxidant. Under optimized conditions, the free amino functionality of the aniline leads to high ortho:meta regioselectivities, now even for anilines bearing a donor substituent in the para position. Finally, the mild and metal-free new access to aminobiphenyls was shown to be applicable on a gram scale.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24524356</pmid><doi>10.1021/jo500063r</doi><tpages>7</tpages></addata></record> |
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| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2014-03, Vol.79 (5), p.2314-2320 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Air Aminobiphenyl Compounds - chemical synthesis Aminobiphenyl Compounds - chemistry Aniline Compounds - chemistry Catalysis Hydrazines - chemistry Molecular Structure Oxidation-Reduction Oxygen - chemistry Stereoisomerism |
| title | Oxidative Radical Arylation of Anilines with Arylhydrazines and Dioxygen from Air |
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