Iridium‐Catalyzed Regio‐ and Enantioselective Hydroarylation of Alkenyl Ethers by Olefin Isomerization
Iridium‐catalyzed hydroarylation of alkenyl ethers, such as allylic and homoallylic ethers, by C−H bond activation gave high yields of the corresponding addition products, where the aryl groups were selectively installed at the α‐carbon atom to the alkoxy group. The reaction involves an isomerizatio...
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| Veröffentlicht in: | Angewandte Chemie 2017-05, Vol.129 (20), p.5699-5703 |
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| creator | Ebe, Yusuke Onoda, Mitsuki Nishimura, Takahiro Yorimitsu, Hideki |
| description | Iridium‐catalyzed hydroarylation of alkenyl ethers, such as allylic and homoallylic ethers, by C−H bond activation gave high yields of the corresponding addition products, where the aryl groups were selectively installed at the α‐carbon atom to the alkoxy group. The reaction involves an isomerization of the alkenyl ethers into the corresponding 1‐alkenyl ethers, which then undergo the regio‐ and enantioselective hydroarylation.
Treffpunkt α: Die iridiumkatalysierte Hydroarylierung von Alkenylethern, beispielsweise (Homo)Allylethern, unter C‐H‐Aktivierung liefert die entsprechenden Additionsprodukte in hohen Ausbeuten. Die Arylgruppen werden selektiv am Kohlenstoffatom in α‐Stellung zur Alkoxygruppe eingeführt. ArF=3,5‐(CF3)2C6H3. |
| doi_str_mv | 10.1002/ange.201702286 |
| format | Article |
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Treffpunkt α: Die iridiumkatalysierte Hydroarylierung von Alkenylethern, beispielsweise (Homo)Allylethern, unter C‐H‐Aktivierung liefert die entsprechenden Additionsprodukte in hohen Ausbeuten. Die Arylgruppen werden selektiv am Kohlenstoffatom in α‐Stellung zur Alkoxygruppe eingeführt. ArF=3,5‐(CF3)2C6H3.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201702286</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkene ; Allylverbindungen ; Aromatic compounds ; C-H-Aktivierung ; Chemistry ; Enantiomers ; Ethers ; Hydrogen bonds ; Iridium ; Isomerisierungen ; Isomerization</subject><ispartof>Angewandte Chemie, 2017-05, Vol.129 (20), p.5699-5703</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-c2286-d530f3672b0f8607730862b5f111922472acabd6d7fdaedd4e8cf075ebd6873c3</citedby><cites>FETCH-LOGICAL-c2286-d530f3672b0f8607730862b5f111922472acabd6d7fdaedd4e8cf075ebd6873c3</cites><orcidid>0000-0002-0153-1888 ; 0000-0002-7032-8613</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fange.201702286$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201702286$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Ebe, Yusuke</creatorcontrib><creatorcontrib>Onoda, Mitsuki</creatorcontrib><creatorcontrib>Nishimura, Takahiro</creatorcontrib><creatorcontrib>Yorimitsu, Hideki</creatorcontrib><title>Iridium‐Catalyzed Regio‐ and Enantioselective Hydroarylation of Alkenyl Ethers by Olefin Isomerization</title><title>Angewandte Chemie</title><description>Iridium‐catalyzed hydroarylation of alkenyl ethers, such as allylic and homoallylic ethers, by C−H bond activation gave high yields of the corresponding addition products, where the aryl groups were selectively installed at the α‐carbon atom to the alkoxy group. The reaction involves an isomerization of the alkenyl ethers into the corresponding 1‐alkenyl ethers, which then undergo the regio‐ and enantioselective hydroarylation.
Treffpunkt α: Die iridiumkatalysierte Hydroarylierung von Alkenylethern, beispielsweise (Homo)Allylethern, unter C‐H‐Aktivierung liefert die entsprechenden Additionsprodukte in hohen Ausbeuten. Die Arylgruppen werden selektiv am Kohlenstoffatom in α‐Stellung zur Alkoxygruppe eingeführt. ArF=3,5‐(CF3)2C6H3.</description><subject>Alkene</subject><subject>Allylverbindungen</subject><subject>Aromatic compounds</subject><subject>C-H-Aktivierung</subject><subject>Chemistry</subject><subject>Enantiomers</subject><subject>Ethers</subject><subject>Hydrogen bonds</subject><subject>Iridium</subject><subject>Isomerisierungen</subject><subject>Isomerization</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkM1OwzAQhC0EEqVw5WyJc8ra-XFyrKrQVqpAQnCOnHhdXFKn2CkoPfEIPCNPQkoRHDmtNPpmd2cIuWQwYgD8WtoljjgwAZynyREZsJizIBSxOCYDgCgKUh5lp-TM-xUAJFxkA7KaO6PMdv35_jGRray7HSp6j0vT9AqVVtHcStuaxmONVWtekc465Rrpulr2sqWNpuP6GW1X07x9Qudp2dG7GrWxdO6bNTqz-ybPyYmWtceLnzkkjzf5w2QWLO6m88l4EVT7vwMVh6DDRPASdJqAECGkCS9jzRjLOI8El5UsVaKEVhKVijCtNIgYey0VYRUOydVh78Y1L1v0bbFqts72JwuWZjHwRISip0YHqnKN9w51sXFm3ccqGBT7Pot9n8Vvn70hOxjeTI3dP3Qxvp3mf94vwlF9EA</recordid><startdate>20170508</startdate><enddate>20170508</enddate><creator>Ebe, Yusuke</creator><creator>Onoda, Mitsuki</creator><creator>Nishimura, Takahiro</creator><creator>Yorimitsu, Hideki</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/0000-0002-0153-1888</orcidid><orcidid>https://orcid.org/0000-0002-7032-8613</orcidid></search><sort><creationdate>20170508</creationdate><title>Iridium‐Catalyzed Regio‐ and Enantioselective Hydroarylation of Alkenyl Ethers by Olefin Isomerization</title><author>Ebe, Yusuke ; Onoda, Mitsuki ; Nishimura, Takahiro ; Yorimitsu, Hideki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2286-d530f3672b0f8607730862b5f111922472acabd6d7fdaedd4e8cf075ebd6873c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkene</topic><topic>Allylverbindungen</topic><topic>Aromatic compounds</topic><topic>C-H-Aktivierung</topic><topic>Chemistry</topic><topic>Enantiomers</topic><topic>Ethers</topic><topic>Hydrogen bonds</topic><topic>Iridium</topic><topic>Isomerisierungen</topic><topic>Isomerization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ebe, Yusuke</creatorcontrib><creatorcontrib>Onoda, Mitsuki</creatorcontrib><creatorcontrib>Nishimura, Takahiro</creatorcontrib><creatorcontrib>Yorimitsu, Hideki</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>Ebe, Yusuke</au><au>Onoda, Mitsuki</au><au>Nishimura, Takahiro</au><au>Yorimitsu, Hideki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Iridium‐Catalyzed Regio‐ and Enantioselective Hydroarylation of Alkenyl Ethers by Olefin Isomerization</atitle><jtitle>Angewandte Chemie</jtitle><date>2017-05-08</date><risdate>2017</risdate><volume>129</volume><issue>20</issue><spage>5699</spage><epage>5703</epage><pages>5699-5703</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>Iridium‐catalyzed hydroarylation of alkenyl ethers, such as allylic and homoallylic ethers, by C−H bond activation gave high yields of the corresponding addition products, where the aryl groups were selectively installed at the α‐carbon atom to the alkoxy group. The reaction involves an isomerization of the alkenyl ethers into the corresponding 1‐alkenyl ethers, which then undergo the regio‐ and enantioselective hydroarylation.
Treffpunkt α: Die iridiumkatalysierte Hydroarylierung von Alkenylethern, beispielsweise (Homo)Allylethern, unter C‐H‐Aktivierung liefert die entsprechenden Additionsprodukte in hohen Ausbeuten. Die Arylgruppen werden selektiv am Kohlenstoffatom in α‐Stellung zur Alkoxygruppe eingeführt. ArF=3,5‐(CF3)2C6H3.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.201702286</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-0153-1888</orcidid><orcidid>https://orcid.org/0000-0002-7032-8613</orcidid></addata></record> |
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| subjects | Alkene Allylverbindungen Aromatic compounds C-H-Aktivierung Chemistry Enantiomers Ethers Hydrogen bonds Iridium Isomerisierungen Isomerization |
| title | Iridium‐Catalyzed Regio‐ and Enantioselective Hydroarylation of Alkenyl Ethers by Olefin Isomerization |
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