Asymmetric Lewis Acid Catalyzed Electrochemical Alkylation
Lewis‐acid catalysis and electrochemistry represent two powerful fields that have found widespread application in organic chemistry. Reported herein is an asymmetric electrosynthesis in combination with a chiral Ni catalyst leading to an intermolecular alkylation reaction in good yields with excelle...
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| Veröffentlicht in: | Angewandte Chemie 2019-05, Vol.131 (21), p.7073-7077 |
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| container_end_page | 7077 |
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| container_issue | 21 |
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| container_title | Angewandte Chemie |
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| creator | Zhang, Qinglin Chang, Xihao Peng, Lingzi Guo, Chang |
| description | Lewis‐acid catalysis and electrochemistry represent two powerful fields that have found widespread application in organic chemistry. Reported herein is an asymmetric electrosynthesis in combination with a chiral Ni catalyst leading to an intermolecular alkylation reaction in good yields with excellent enantioselectivities (up to 97 % ee). Mechanistic studies suggest that the Lewis‐acid‐bound radical intermediate from a single‐electron anodic oxidation selectively reacts with the benzylic radical species to generate the desired adducts.
Elektrifizierend: Mit einem chiralen Ni‐Katalysator wurde eine effiziente asymmetrische Elektrosynthese mit hohen Ausbeuten und hervorragenden Enantioselektivitäten entwickelt. Mechanistische Studien deuten darauf hin, dass das Lewis‐Säure‐gebundene radikalische Zwischenprodukt, das aus einer anodischen Ein‐Elektronen‐Oxidation stammt, selektiv mit einer benzylischen Radikalspezies reagiert, um die gewünschten Addukte zu bilden. |
| doi_str_mv | 10.1002/ange.201901801 |
| format | Article |
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Elektrifizierend: Mit einem chiralen Ni‐Katalysator wurde eine effiziente asymmetrische Elektrosynthese mit hohen Ausbeuten und hervorragenden Enantioselektivitäten entwickelt. Mechanistische Studien deuten darauf hin, dass das Lewis‐Säure‐gebundene radikalische Zwischenprodukt, das aus einer anodischen Ein‐Elektronen‐Oxidation stammt, selektiv mit einer benzylischen Radikalspezies reagiert, um die gewünschten Addukte zu bilden.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201901801</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Adducts ; Alkylation ; Anodizing ; Asymmetrische Katalyse ; Catalysis ; Chemistry ; Electrochemistry ; Elektrochemie ; Lewis acid ; Lewis-Säuren ; Nickel ; Organic chemistry ; Oxidation ; Radikale</subject><ispartof>Angewandte Chemie, 2019-05, Vol.131 (21), p.7073-7077</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1621-d2e1e31ef033eff380dc71f82a721ada8f42fd95f0ec503f2578c66a29e622bf3</citedby><cites>FETCH-LOGICAL-c1621-d2e1e31ef033eff380dc71f82a721ada8f42fd95f0ec503f2578c66a29e622bf3</cites><orcidid>0000-0003-4022-9582</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.201901801$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201901801$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Zhang, Qinglin</creatorcontrib><creatorcontrib>Chang, Xihao</creatorcontrib><creatorcontrib>Peng, Lingzi</creatorcontrib><creatorcontrib>Guo, Chang</creatorcontrib><title>Asymmetric Lewis Acid Catalyzed Electrochemical Alkylation</title><title>Angewandte Chemie</title><description>Lewis‐acid catalysis and electrochemistry represent two powerful fields that have found widespread application in organic chemistry. Reported herein is an asymmetric electrosynthesis in combination with a chiral Ni catalyst leading to an intermolecular alkylation reaction in good yields with excellent enantioselectivities (up to 97 % ee). Mechanistic studies suggest that the Lewis‐acid‐bound radical intermediate from a single‐electron anodic oxidation selectively reacts with the benzylic radical species to generate the desired adducts.
Elektrifizierend: Mit einem chiralen Ni‐Katalysator wurde eine effiziente asymmetrische Elektrosynthese mit hohen Ausbeuten und hervorragenden Enantioselektivitäten entwickelt. Mechanistische Studien deuten darauf hin, dass das Lewis‐Säure‐gebundene radikalische Zwischenprodukt, das aus einer anodischen Ein‐Elektronen‐Oxidation stammt, selektiv mit einer benzylischen Radikalspezies reagiert, um die gewünschten Addukte zu bilden.</description><subject>Adducts</subject><subject>Alkylation</subject><subject>Anodizing</subject><subject>Asymmetrische Katalyse</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Electrochemistry</subject><subject>Elektrochemie</subject><subject>Lewis acid</subject><subject>Lewis-Säuren</subject><subject>Nickel</subject><subject>Organic chemistry</subject><subject>Oxidation</subject><subject>Radikale</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkLFOwzAQQC0EEqWwMkdiTjmfk9hhi6pSkCpYYLaMcwaXpCl2KhS-nlRFMDLd8t7d6TF2yWHGAfDabF5phsBL4Ar4EZvwHHkqZC6P2QQgy1KFWXnKzmJcA0CBspywmyoObUt98DZZ0aePSWV9ncxNb5rhi-pk0ZDtQ2ffqPXWNEnVvA-N6X23OWcnzjSRLn7mlD3fLp7md-nqcXk_r1ap5cX4QI3ESXByIAQ5JxTUVnKn0EjkpjbKZejqMndANgfhMJfKFoXBkgrEFyem7Oqwdxu6jx3FXq-7XdiMJzUiComKF9lIzQ6UDV2MgZzeBt-aMGgOet9H7_vo3z6jUB6ET9_Q8A-tq4fl4s_9BotYaSE</recordid><startdate>20190520</startdate><enddate>20190520</enddate><creator>Zhang, Qinglin</creator><creator>Chang, Xihao</creator><creator>Peng, Lingzi</creator><creator>Guo, Chang</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/0000-0003-4022-9582</orcidid></search><sort><creationdate>20190520</creationdate><title>Asymmetric Lewis Acid Catalyzed Electrochemical Alkylation</title><author>Zhang, Qinglin ; Chang, Xihao ; Peng, Lingzi ; Guo, Chang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1621-d2e1e31ef033eff380dc71f82a721ada8f42fd95f0ec503f2578c66a29e622bf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Adducts</topic><topic>Alkylation</topic><topic>Anodizing</topic><topic>Asymmetrische Katalyse</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Electrochemistry</topic><topic>Elektrochemie</topic><topic>Lewis acid</topic><topic>Lewis-Säuren</topic><topic>Nickel</topic><topic>Organic chemistry</topic><topic>Oxidation</topic><topic>Radikale</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Qinglin</creatorcontrib><creatorcontrib>Chang, Xihao</creatorcontrib><creatorcontrib>Peng, Lingzi</creatorcontrib><creatorcontrib>Guo, Chang</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>Zhang, Qinglin</au><au>Chang, Xihao</au><au>Peng, Lingzi</au><au>Guo, Chang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Lewis Acid Catalyzed Electrochemical Alkylation</atitle><jtitle>Angewandte Chemie</jtitle><date>2019-05-20</date><risdate>2019</risdate><volume>131</volume><issue>21</issue><spage>7073</spage><epage>7077</epage><pages>7073-7077</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>Lewis‐acid catalysis and electrochemistry represent two powerful fields that have found widespread application in organic chemistry. Reported herein is an asymmetric electrosynthesis in combination with a chiral Ni catalyst leading to an intermolecular alkylation reaction in good yields with excellent enantioselectivities (up to 97 % ee). Mechanistic studies suggest that the Lewis‐acid‐bound radical intermediate from a single‐electron anodic oxidation selectively reacts with the benzylic radical species to generate the desired adducts.
Elektrifizierend: Mit einem chiralen Ni‐Katalysator wurde eine effiziente asymmetrische Elektrosynthese mit hohen Ausbeuten und hervorragenden Enantioselektivitäten entwickelt. Mechanistische Studien deuten darauf hin, dass das Lewis‐Säure‐gebundene radikalische Zwischenprodukt, das aus einer anodischen Ein‐Elektronen‐Oxidation stammt, selektiv mit einer benzylischen Radikalspezies reagiert, um die gewünschten Addukte zu bilden.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.201901801</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-4022-9582</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Adducts Alkylation Anodizing Asymmetrische Katalyse Catalysis Chemistry Electrochemistry Elektrochemie Lewis acid Lewis-Säuren Nickel Organic chemistry Oxidation Radikale |
| title | Asymmetric Lewis Acid Catalyzed Electrochemical Alkylation |
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