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Fluorine Effects on Group Migration via a Rhodium(V) Nitrenoid Intermediate
An unprecedented rhodium(III)‐catalyzed hydroarylation of α,α‐difluoromethylene alkynes with N‐pivaloxyl aroylamides through sequential C−H activation and aryl migration is detailed herein. A large array of α,α‐difluoromethylene alkynes and N‐pivaloxyl aryl amides were amenable to this transformatio...
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| Published in: | Angewandte Chemie 2017-11, Vol.129 (47), p.15114-15118 |
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| Main Authors: | , , |
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| cited_by | cdi_FETCH-LOGICAL-c2285-ad5b347b7f863406558056c442ae757e7dacc8704832da7c8bae13db7a6bea953 |
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| cites | cdi_FETCH-LOGICAL-c2285-ad5b347b7f863406558056c442ae757e7dacc8704832da7c8bae13db7a6bea953 |
| container_end_page | 15118 |
| container_issue | 47 |
| container_start_page | 15114 |
| container_title | Angewandte Chemie |
| container_volume | 129 |
| creator | Wang, Cheng‐Qiang Zhang, Yu Feng, Chao |
| description | An unprecedented rhodium(III)‐catalyzed hydroarylation of α,α‐difluoromethylene alkynes with N‐pivaloxyl aroylamides through sequential C−H activation and aryl migration is detailed herein. A large array of α,α‐difluoromethylene alkynes and N‐pivaloxyl aryl amides were amenable to this transformation, thus providing a novel synthetic protocol for the construction of difluorinated 2‐alkenyl aniline derivatives in high yields and with excellent regioselectivity. Notably, unique fluorine effects were found to underlie the thus unconventional reaction manifold.
Neue Wege erkunden: Die Rhodium(III)‐katalysierte Hydroarylierung von α,α‐Difluormethylenalkinen mit N‐Pivaloyloxyarylamiden ermöglicht die effiziente regiospezifische Synthese von difluorierten 2‐Alkenylanilinen (siehe Schema). Die Fluorsubstituenten in den Alkinsubstraten lenken den Reaktionsverlauf vom konventionellen Anellierungsweg hin zu einem Hydroarylierungsprozess, der eine Lossen‐Umlagerung einschließt. |
| doi_str_mv | 10.1002/ange.201708505 |
| format | article |
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Neue Wege erkunden: Die Rhodium(III)‐katalysierte Hydroarylierung von α,α‐Difluormethylenalkinen mit N‐Pivaloyloxyarylamiden ermöglicht die effiziente regiospezifische Synthese von difluorierten 2‐Alkenylanilinen (siehe Schema). Die Fluorsubstituenten in den Alkinsubstraten lenken den Reaktionsverlauf vom konventionellen Anellierungsweg hin zu einem Hydroarylierungsprozess, der eine Lossen‐Umlagerung einschließt.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201708505</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; Amides ; Aniline ; Aromatic compounds ; C-H-Aktivierung ; Chemistry ; Fluoreffekte ; Fluorine ; Hydroarylierungen ; Lossen-Umlagerung ; Migration ; Organic compounds ; Regioselectivity ; Rhodium</subject><ispartof>Angewandte Chemie, 2017-11, Vol.129 (47), p.15114-15118</ispartof><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-c2285-ad5b347b7f863406558056c442ae757e7dacc8704832da7c8bae13db7a6bea953</citedby><cites>FETCH-LOGICAL-c2285-ad5b347b7f863406558056c442ae757e7dacc8704832da7c8bae13db7a6bea953</cites><orcidid>0000-0003-4494-6845</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Wang, Cheng‐Qiang</creatorcontrib><creatorcontrib>Zhang, Yu</creatorcontrib><creatorcontrib>Feng, Chao</creatorcontrib><title>Fluorine Effects on Group Migration via a Rhodium(V) Nitrenoid Intermediate</title><title>Angewandte Chemie</title><description>An unprecedented rhodium(III)‐catalyzed hydroarylation of α,α‐difluoromethylene alkynes with N‐pivaloxyl aroylamides through sequential C−H activation and aryl migration is detailed herein. A large array of α,α‐difluoromethylene alkynes and N‐pivaloxyl aryl amides were amenable to this transformation, thus providing a novel synthetic protocol for the construction of difluorinated 2‐alkenyl aniline derivatives in high yields and with excellent regioselectivity. Notably, unique fluorine effects were found to underlie the thus unconventional reaction manifold.
Neue Wege erkunden: Die Rhodium(III)‐katalysierte Hydroarylierung von α,α‐Difluormethylenalkinen mit N‐Pivaloyloxyarylamiden ermöglicht die effiziente regiospezifische Synthese von difluorierten 2‐Alkenylanilinen (siehe Schema). Die Fluorsubstituenten in den Alkinsubstraten lenken den Reaktionsverlauf vom konventionellen Anellierungsweg hin zu einem Hydroarylierungsprozess, der eine Lossen‐Umlagerung einschließt.</description><subject>Alkynes</subject><subject>Amides</subject><subject>Aniline</subject><subject>Aromatic compounds</subject><subject>C-H-Aktivierung</subject><subject>Chemistry</subject><subject>Fluoreffekte</subject><subject>Fluorine</subject><subject>Hydroarylierungen</subject><subject>Lossen-Umlagerung</subject><subject>Migration</subject><subject>Organic compounds</subject><subject>Regioselectivity</subject><subject>Rhodium</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkMFLwzAUh4MoOKdXzwEveuh8SZMmPY6xzeGcIOo1pO3rzNiambaT_fd2TPTo6fHg-37v8SPkmsGAAfB7Wy1xwIEp0BLkCekxyVkUK6lOSQ9AiEhzkZ6Ti7peAUDCVdojj5N164OrkI7LEvOmpr6i0-DbLX1yy2Ab1-07Z6mlLx--cO3m9v2OLlwTsPKuoLOqwbDBwtkGL8lZadc1Xv3MPnmbjF9HD9H8eTobDedRzrmWkS1kFguVqVInsYBESg0yyYXgFrtnURU2z7UCoWNeWJXrzCKLi0zZJEObyrhPbo652-A_W6wbs_JtqLqThqVJnKqUsQM1OFJ58HUdsDTb4DY27A0DcyjMHAozv4V1QnoUvtwa9__QZriYjv_cbwlebnc</recordid><startdate>20171120</startdate><enddate>20171120</enddate><creator>Wang, Cheng‐Qiang</creator><creator>Zhang, Yu</creator><creator>Feng, Chao</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0003-4494-6845</orcidid></search><sort><creationdate>20171120</creationdate><title>Fluorine Effects on Group Migration via a Rhodium(V) Nitrenoid Intermediate</title><author>Wang, Cheng‐Qiang ; Zhang, Yu ; Feng, Chao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2285-ad5b347b7f863406558056c442ae757e7dacc8704832da7c8bae13db7a6bea953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkynes</topic><topic>Amides</topic><topic>Aniline</topic><topic>Aromatic compounds</topic><topic>C-H-Aktivierung</topic><topic>Chemistry</topic><topic>Fluoreffekte</topic><topic>Fluorine</topic><topic>Hydroarylierungen</topic><topic>Lossen-Umlagerung</topic><topic>Migration</topic><topic>Organic compounds</topic><topic>Regioselectivity</topic><topic>Rhodium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Cheng‐Qiang</creatorcontrib><creatorcontrib>Zhang, Yu</creatorcontrib><creatorcontrib>Feng, Chao</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Cheng‐Qiang</au><au>Zhang, Yu</au><au>Feng, Chao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Fluorine Effects on Group Migration via a Rhodium(V) Nitrenoid Intermediate</atitle><jtitle>Angewandte Chemie</jtitle><date>2017-11-20</date><risdate>2017</risdate><volume>129</volume><issue>47</issue><spage>15114</spage><epage>15118</epage><pages>15114-15118</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>An unprecedented rhodium(III)‐catalyzed hydroarylation of α,α‐difluoromethylene alkynes with N‐pivaloxyl aroylamides through sequential C−H activation and aryl migration is detailed herein. A large array of α,α‐difluoromethylene alkynes and N‐pivaloxyl aryl amides were amenable to this transformation, thus providing a novel synthetic protocol for the construction of difluorinated 2‐alkenyl aniline derivatives in high yields and with excellent regioselectivity. Notably, unique fluorine effects were found to underlie the thus unconventional reaction manifold.
Neue Wege erkunden: Die Rhodium(III)‐katalysierte Hydroarylierung von α,α‐Difluormethylenalkinen mit N‐Pivaloyloxyarylamiden ermöglicht die effiziente regiospezifische Synthese von difluorierten 2‐Alkenylanilinen (siehe Schema). Die Fluorsubstituenten in den Alkinsubstraten lenken den Reaktionsverlauf vom konventionellen Anellierungsweg hin zu einem Hydroarylierungsprozess, der eine Lossen‐Umlagerung einschließt.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.201708505</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-4494-6845</orcidid></addata></record> |
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| identifier | ISSN: 0044-8249 |
| ispartof | Angewandte Chemie, 2017-11, Vol.129 (47), p.15114-15118 |
| issn | 0044-8249 1521-3757 |
| language | eng |
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| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Alkynes Amides Aniline Aromatic compounds C-H-Aktivierung Chemistry Fluoreffekte Fluorine Hydroarylierungen Lossen-Umlagerung Migration Organic compounds Regioselectivity Rhodium |
| title | Fluorine Effects on Group Migration via a Rhodium(V) Nitrenoid Intermediate |
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