Ligand-Controlled α- and β-Arylation of Acyclic N-Boc Amines
The palladium‐catalyzed ligand‐controlled arylation of α‐zincated acyclic amines, obtained by directed α‐lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α‐arylated Boc‐protected amines, more flexible N‐phenylazole‐based phosphine ligands induced major β‐arylation through mig...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2014-03, Vol.53 (10), p.2678-2682 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Millet, Anthony Dailler, David Larini, Paolo Baudoin, Olivier |
| description | The palladium‐catalyzed ligand‐controlled arylation of α‐zincated acyclic amines, obtained by directed α‐lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α‐arylated Boc‐protected amines, more flexible N‐phenylazole‐based phosphine ligands induced major β‐arylation through migrative cross‐coupling.
All manner of control: The arylation of α‐zincated acyclic Boc‐protected amines was selectively performed at the α‐ or β‐position in a ligand‐controlled manner. α‐Arylation occurs by direct reductive elimination of the α‐palladated intermediate whereas β‐arylation involves palladium migration along the alkyl chain. Boc=tert‐butoxycarbonyl. |
| doi_str_mv | 10.1002/anie.201310904 |
| format | Article |
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All manner of control: The arylation of α‐zincated acyclic Boc‐protected amines was selectively performed at the α‐ or β‐position in a ligand‐controlled manner. α‐Arylation occurs by direct reductive elimination of the α‐palladated intermediate whereas β‐arylation involves palladium migration along the alkyl chain. Boc=tert‐butoxycarbonyl.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201310904</identifier><identifier>PMID: 24504659</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Amines - chemical synthesis ; Amines - chemistry ; arylation ; Catalysis ; cross-coupling ; CC coupling ; density functional calculations ; Ligands ; Molecular Conformation ; palladium ; Palladium - chemistry</subject><ispartof>Angewandte Chemie International Edition, 2014-03, Vol.53 (10), p.2678-2682</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4234-2202ee4e6cd2c192a3714678abb57e570d73367c8d120d633d74a55cb1859b13</citedby><cites>FETCH-LOGICAL-c4234-2202ee4e6cd2c192a3714678abb57e570d73367c8d120d633d74a55cb1859b13</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%2Fanie.201310904$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201310904$$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/24504659$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Millet, Anthony</creatorcontrib><creatorcontrib>Dailler, David</creatorcontrib><creatorcontrib>Larini, Paolo</creatorcontrib><creatorcontrib>Baudoin, Olivier</creatorcontrib><title>Ligand-Controlled α- and β-Arylation of Acyclic N-Boc Amines</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>The palladium‐catalyzed ligand‐controlled arylation of α‐zincated acyclic amines, obtained by directed α‐lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α‐arylated Boc‐protected amines, more flexible N‐phenylazole‐based phosphine ligands induced major β‐arylation through migrative cross‐coupling.
All manner of control: The arylation of α‐zincated acyclic Boc‐protected amines was selectively performed at the α‐ or β‐position in a ligand‐controlled manner. α‐Arylation occurs by direct reductive elimination of the α‐palladated intermediate whereas β‐arylation involves palladium migration along the alkyl chain. Boc=tert‐butoxycarbonyl.</description><subject>Amines - chemical synthesis</subject><subject>Amines - chemistry</subject><subject>arylation</subject><subject>Catalysis</subject><subject>cross-coupling</subject><subject>CC coupling</subject><subject>density functional calculations</subject><subject>Ligands</subject><subject>Molecular Conformation</subject><subject>palladium</subject><subject>Palladium - chemistry</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1PwjAchxujEUWvHs2OXop9XbeLySQIJAQxIXJsuq6YatlwHdF9LP0gfCZHhsSbp_7TPL_n8ABwhVEPI0RuVW5NjyBMMYoROwJnmBMMqRD0uLkZpVBEHHfAufevDR9FKDwFHcI4YiGPz8DdxL6oPIP9Iq_KwjmTBdsvGDRfwfYbJmXtVGWLPCiWQaJr7awOpvC-0EGysrnxF-BkqZw3l_u3C-YPg3l_BCePw3E_mUDNCGWQEESMYSbUGdE4JooKzEIRqTTlwnCBMkFpKHSUYYKykNJMMMW5TnHE4xTTLrhpteuyeN8YX8mV9do4p3JTbLzEHFHOoqZIg_ZaVJeF96VZynVpV6qsJUZyl0zukslDsmZwvXdv0pXJDvhvowaIW-DDOlP_o5PJdDz4K4ft1vrKfB62qnyToaCCy8V0KEezGSWL5yfJ6A988IV_</recordid><startdate>20140303</startdate><enddate>20140303</enddate><creator>Millet, Anthony</creator><creator>Dailler, David</creator><creator>Larini, Paolo</creator><creator>Baudoin, Olivier</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><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>20140303</creationdate><title>Ligand-Controlled α- and β-Arylation of Acyclic N-Boc Amines</title><author>Millet, Anthony ; Dailler, David ; Larini, Paolo ; Baudoin, Olivier</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4234-2202ee4e6cd2c192a3714678abb57e570d73367c8d120d633d74a55cb1859b13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Amines - chemical synthesis</topic><topic>Amines - chemistry</topic><topic>arylation</topic><topic>Catalysis</topic><topic>cross-coupling</topic><topic>CC coupling</topic><topic>density functional calculations</topic><topic>Ligands</topic><topic>Molecular Conformation</topic><topic>palladium</topic><topic>Palladium - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Millet, Anthony</creatorcontrib><creatorcontrib>Dailler, David</creatorcontrib><creatorcontrib>Larini, Paolo</creatorcontrib><creatorcontrib>Baudoin, Olivier</creatorcontrib><collection>Istex</collection><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>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Millet, Anthony</au><au>Dailler, David</au><au>Larini, Paolo</au><au>Baudoin, Olivier</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ligand-Controlled α- and β-Arylation of Acyclic N-Boc Amines</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2014-03-03</date><risdate>2014</risdate><volume>53</volume><issue>10</issue><spage>2678</spage><epage>2682</epage><pages>2678-2682</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The palladium‐catalyzed ligand‐controlled arylation of α‐zincated acyclic amines, obtained by directed α‐lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α‐arylated Boc‐protected amines, more flexible N‐phenylazole‐based phosphine ligands induced major β‐arylation through migrative cross‐coupling.
All manner of control: The arylation of α‐zincated acyclic Boc‐protected amines was selectively performed at the α‐ or β‐position in a ligand‐controlled manner. α‐Arylation occurs by direct reductive elimination of the α‐palladated intermediate whereas β‐arylation involves palladium migration along the alkyl chain. Boc=tert‐butoxycarbonyl.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24504659</pmid><doi>10.1002/anie.201310904</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Amines - chemical synthesis Amines - chemistry arylation Catalysis cross-coupling CC coupling density functional calculations Ligands Molecular Conformation palladium Palladium - chemistry |
| title | Ligand-Controlled α- and β-Arylation of Acyclic N-Boc Amines |
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