Free-Amine-Directed Alkenylation of C(sp2)H and Cycloamination by Palladium Catalysis
A new protocol for the palladium‐catalyzed free‐amine‐directed alkenylation of C(sp2)H bonds and cycloamination is described. Substituted biaryl‐2‐amines react with various alkenes, including electron‐deficient alkenes, aryl alkenes and alkyl alkenes, to give the corresponding phenanthridines with...
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| Veröffentlicht in: | Chemistry : a European journal 2012-12, Vol.18 (49), p.15816-15821 |
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| container_issue | 49 |
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| container_title | Chemistry : a European journal |
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| creator | Liang, Zunjun Ju, Long Xie, Yongju Huang, Lehao Zhang, Yuhong |
| description | A new protocol for the palladium‐catalyzed free‐amine‐directed alkenylation of C(sp2)H bonds and cycloamination is described. Substituted biaryl‐2‐amines react with various alkenes, including electron‐deficient alkenes, aryl alkenes and alkyl alkenes, to give the corresponding phenanthridines with exclusive regioselectivity. The use of α‐branched styrenes leads to the formation of tricyclic compounds with a seven‐membered amine ring. The method operates through a free‐amine‐directed alkenylation and a subsequent hydroamination cyclization reaction.
Seven‐membered cycloamination: A new protocol for the palladium‐catalyzed free‐amine‐directed alkenylation of C(sp2)H bonds and subsequent cycloamination is described (see scheme). Substituted biaryl‐2‐amines react with various alkenes to give the corresponding phenanthridines with exclusive regioselectivity. The use of α‐branched styrenes leads to the formation of tricyclic compounds with a seven‐membered amine ring. |
| doi_str_mv | 10.1002/chem.201202672 |
| format | Article |
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Seven‐membered cycloamination: A new protocol for the palladium‐catalyzed free‐amine‐directed alkenylation of C(sp2)H bonds and subsequent cycloamination is described (see scheme). Substituted biaryl‐2‐amines react with various alkenes to give the corresponding phenanthridines with exclusive regioselectivity. The use of α‐branched styrenes leads to the formation of tricyclic compounds with a seven‐membered amine ring.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201202672</identifier><identifier>PMID: 23055185</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkenes ; alkenylation ; amination ; Amines ; Aromatic compounds ; Catalysis ; Chemistry ; cyclization ; CH activation ; Formations ; Palladium ; phenanthridines ; Styrenes</subject><ispartof>Chemistry : a European journal, 2012-12, Vol.18 (49), p.15816-15821</ispartof><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5102-e1fd296ca0aeec9766bf17c372c453c294e2cea2139bd2337f1d3d3fa51ce5853</citedby><cites>FETCH-LOGICAL-c5102-e1fd296ca0aeec9766bf17c372c453c294e2cea2139bd2337f1d3d3fa51ce5853</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1411,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23055185$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liang, Zunjun</creatorcontrib><creatorcontrib>Ju, Long</creatorcontrib><creatorcontrib>Xie, Yongju</creatorcontrib><creatorcontrib>Huang, Lehao</creatorcontrib><creatorcontrib>Zhang, Yuhong</creatorcontrib><title>Free-Amine-Directed Alkenylation of C(sp2)H and Cycloamination by Palladium Catalysis</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A new protocol for the palladium‐catalyzed free‐amine‐directed alkenylation of C(sp2)H bonds and cycloamination is described. Substituted biaryl‐2‐amines react with various alkenes, including electron‐deficient alkenes, aryl alkenes and alkyl alkenes, to give the corresponding phenanthridines with exclusive regioselectivity. The use of α‐branched styrenes leads to the formation of tricyclic compounds with a seven‐membered amine ring. The method operates through a free‐amine‐directed alkenylation and a subsequent hydroamination cyclization reaction.
Seven‐membered cycloamination: A new protocol for the palladium‐catalyzed free‐amine‐directed alkenylation of C(sp2)H bonds and subsequent cycloamination is described (see scheme). Substituted biaryl‐2‐amines react with various alkenes to give the corresponding phenanthridines with exclusive regioselectivity. The use of α‐branched styrenes leads to the formation of tricyclic compounds with a seven‐membered amine ring.</description><subject>Alkenes</subject><subject>alkenylation</subject><subject>amination</subject><subject>Amines</subject><subject>Aromatic compounds</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>cyclization</subject><subject>CH activation</subject><subject>Formations</subject><subject>Palladium</subject><subject>phenanthridines</subject><subject>Styrenes</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqF0c1u1DAUBWALgei0sGWJIrEpiwz2dWzHy1HozCCVggQIxMbyODfCbX4GOxHN8_AgPBKvQEYpI8SmK2--c2zrEPKM0SWjFF65b9gsgTKgIBU8IAsmgKVcSfGQLKjOVCoF1yfkNMZrSqmWnD8mJ8CpECwXC_JlHRDTVeNbTF_7gK7HMlnVN9iOte191yZdlRTncQ8vf__8tU1sWybF6OrOTpEZ7Mbkva1rW_qhSQrb23qMPj4hjypbR3x6d56RT-uLj8U2vXy3eVOsLlMnGIUUWVWCls5Si-i0knJXMeW4ApcJ7kBnCA4tMK53JXCuKlbykldWMIciF_yMnM-9-9B9HzD2pvHR4fSeFrshGqZUTjNNmbqfMq2yfLrjQF_8R6-7IbTTRyaVS6ASOJvUclYudDEGrMw--MaG0TBqDvOYwzzmOM8UeH5XO-waLI_87x4T0DP44Wsc76kzxfbi7b_l6Zz1scfbY9aGGyMVV8J8vtoYKq_Wmw88M1_5H4tvqkI</recordid><startdate>20121203</startdate><enddate>20121203</enddate><creator>Liang, Zunjun</creator><creator>Ju, Long</creator><creator>Xie, Yongju</creator><creator>Huang, Lehao</creator><creator>Zhang, Yuhong</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>20121203</creationdate><title>Free-Amine-Directed Alkenylation of C(sp2)H and Cycloamination by Palladium Catalysis</title><author>Liang, Zunjun ; Ju, Long ; Xie, Yongju ; Huang, Lehao ; Zhang, Yuhong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5102-e1fd296ca0aeec9766bf17c372c453c294e2cea2139bd2337f1d3d3fa51ce5853</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Alkenes</topic><topic>alkenylation</topic><topic>amination</topic><topic>Amines</topic><topic>Aromatic compounds</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>cyclization</topic><topic>CH activation</topic><topic>Formations</topic><topic>Palladium</topic><topic>phenanthridines</topic><topic>Styrenes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liang, Zunjun</creatorcontrib><creatorcontrib>Ju, Long</creatorcontrib><creatorcontrib>Xie, Yongju</creatorcontrib><creatorcontrib>Huang, Lehao</creatorcontrib><creatorcontrib>Zhang, Yuhong</creatorcontrib><collection>Istex</collection><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, Zunjun</au><au>Ju, Long</au><au>Xie, Yongju</au><au>Huang, Lehao</au><au>Zhang, Yuhong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Free-Amine-Directed Alkenylation of C(sp2)H and Cycloamination by Palladium Catalysis</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2012-12-03</date><risdate>2012</risdate><volume>18</volume><issue>49</issue><spage>15816</spage><epage>15821</epage><pages>15816-15821</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>A new protocol for the palladium‐catalyzed free‐amine‐directed alkenylation of C(sp2)H bonds and cycloamination is described. Substituted biaryl‐2‐amines react with various alkenes, including electron‐deficient alkenes, aryl alkenes and alkyl alkenes, to give the corresponding phenanthridines with exclusive regioselectivity. The use of α‐branched styrenes leads to the formation of tricyclic compounds with a seven‐membered amine ring. The method operates through a free‐amine‐directed alkenylation and a subsequent hydroamination cyclization reaction.
Seven‐membered cycloamination: A new protocol for the palladium‐catalyzed free‐amine‐directed alkenylation of C(sp2)H bonds and subsequent cycloamination is described (see scheme). Substituted biaryl‐2‐amines react with various alkenes to give the corresponding phenanthridines with exclusive regioselectivity. The use of α‐branched styrenes leads to the formation of tricyclic compounds with a seven‐membered amine ring.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>23055185</pmid><doi>10.1002/chem.201202672</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Chemistry : a European journal, 2012-12, Vol.18 (49), p.15816-15821 |
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| language | eng |
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| source | Wiley-Blackwell Journals |
| subjects | Alkenes alkenylation amination Amines Aromatic compounds Catalysis Chemistry cyclization CH activation Formations Palladium phenanthridines Styrenes |
| title | Free-Amine-Directed Alkenylation of C(sp2)H and Cycloamination by Palladium Catalysis |
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