A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters
We report herein the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin‐3‐ol or 4‐dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alk...
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| Veröffentlicht in: | Angewandte Chemie 2017-11, Vol.129 (47), p.15332-15336 |
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| container_title | Angewandte Chemie |
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| creator | Lima, Fabio Sharma, Upendra K. Grunenberg, Lars Saha, Debasmita Johannsen, Sandra Sedelmeier, Joerg Van der Eycken, Erik V. Ley, Steven V. |
| description | We report herein the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin‐3‐ol or 4‐dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alkyl boronic acids to react with electron‐deficient olefins via radical addition to efficiently form C−C coupled products in a redox‐neutral fashion. The Lewis base catalyst was shown to form a redox‐active complex with either the boronic esters or the trimeric form of the boronic acids (boroxines) in solution.
Ein duales Katalysatorsystem bestehend aus einer Lewis‐Base (LB), z. B. Chinucludin‐3‐ol oder 4‐Dimethylaminopyridin, und einem Photoredoxkatalysator ermöglicht die Erzeugung von Kohlenstoffradikalen aus Boronsäuren und ‐estern. Verschiedene Alkylboronsäureester sowie Aryl‐ und Alkylboronsäuren reagieren mit elektronenarmen Olefinen in einem redoxneutralen Prozess zu C‐C‐Kupplungsprodukten. |
| doi_str_mv | 10.1002/ange.201709690 |
| format | Article |
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Ein duales Katalysatorsystem bestehend aus einer Lewis‐Base (LB), z. B. Chinucludin‐3‐ol oder 4‐Dimethylaminopyridin, und einem Photoredoxkatalysator ermöglicht die Erzeugung von Kohlenstoffradikalen aus Boronsäuren und ‐estern. Verschiedene Alkylboronsäureester sowie Aryl‐ und Alkylboronsäuren reagieren mit elektronenarmen Olefinen in einem redoxneutralen Prozess zu C‐C‐Kupplungsprodukten.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201709690</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Acids ; Alkenes ; Aromatic compounds ; Boronsäuren ; Catalysis ; Catalysts ; Chemistry ; Esters ; Kreuzkupplungen ; Lewis base ; Lewis-Basen-Katalyse ; Photoredoxkatalyse ; Synthesemethoden</subject><ispartof>Angewandte Chemie, 2017-11, Vol.129 (47), p.15332-15336</ispartof><rights>2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2680-8f1ab56edd87bd60bd08ae10e7085f5f0ae1ce315914f92ff4a6589a8dae743</citedby><cites>FETCH-LOGICAL-c2680-8f1ab56edd87bd60bd08ae10e7085f5f0ae1ce315914f92ff4a6589a8dae743</cites><orcidid>0000-0002-7816-0042 ; 0000-0003-2127-9568</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.201709690$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201709690$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Lima, Fabio</creatorcontrib><creatorcontrib>Sharma, Upendra K.</creatorcontrib><creatorcontrib>Grunenberg, Lars</creatorcontrib><creatorcontrib>Saha, Debasmita</creatorcontrib><creatorcontrib>Johannsen, Sandra</creatorcontrib><creatorcontrib>Sedelmeier, Joerg</creatorcontrib><creatorcontrib>Van der Eycken, Erik V.</creatorcontrib><creatorcontrib>Ley, Steven V.</creatorcontrib><title>A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters</title><title>Angewandte Chemie</title><description>We report herein the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin‐3‐ol or 4‐dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alkyl boronic acids to react with electron‐deficient olefins via radical addition to efficiently form C−C coupled products in a redox‐neutral fashion. The Lewis base catalyst was shown to form a redox‐active complex with either the boronic esters or the trimeric form of the boronic acids (boroxines) in solution.
Ein duales Katalysatorsystem bestehend aus einer Lewis‐Base (LB), z. B. Chinucludin‐3‐ol oder 4‐Dimethylaminopyridin, und einem Photoredoxkatalysator ermöglicht die Erzeugung von Kohlenstoffradikalen aus Boronsäuren und ‐estern. Verschiedene Alkylboronsäureester sowie Aryl‐ und Alkylboronsäuren reagieren mit elektronenarmen Olefinen in einem redoxneutralen Prozess zu C‐C‐Kupplungsprodukten.</description><subject>Acids</subject><subject>Alkenes</subject><subject>Aromatic compounds</subject><subject>Boronsäuren</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Esters</subject><subject>Kreuzkupplungen</subject><subject>Lewis base</subject><subject>Lewis-Basen-Katalyse</subject><subject>Photoredoxkatalyse</subject><subject>Synthesemethoden</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNqFkL1PwzAQxS0EEqWwMltiTjknsWOPaVUKUgVIsDBZbnymqUpc7EDpf4-rIhiZTu_0e_fxCLlkMGIA-bXpXnGUA6tACQVHZMB4zrKi4tUxGQCUZSbzUp2SsxhXACDySg3IS03nuG0jHZuIdGJ6s97FJOvNJnjTLKnzgfZLpI9L3_uA1n_RuunbT9O3vqPe0bEPvmub1G1tpKazdBp7DPGcnDizjnjxU4fk6Wb6PLnN5g-zu0k9z5pcSMikY2bBBVorq4UVsLAgDTLACiR33EESDRaMK1Y6lTtXGsGlMtIarMpiSK4OU9O57x8Ye73yH6FLCzVTolDp5UImanSgmuBjDOj0JrRvJuw0A70PT-_D07_hJYM6GLbtGnf_0Lq-n03_vN-tKHNn</recordid><startdate>20171120</startdate><enddate>20171120</enddate><creator>Lima, Fabio</creator><creator>Sharma, Upendra K.</creator><creator>Grunenberg, Lars</creator><creator>Saha, Debasmita</creator><creator>Johannsen, Sandra</creator><creator>Sedelmeier, Joerg</creator><creator>Van der Eycken, Erik V.</creator><creator>Ley, Steven V.</creator><general>Wiley Subscription Services, Inc</general><scope>24P</scope><scope>WIN</scope><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/0000-0002-7816-0042</orcidid><orcidid>https://orcid.org/0000-0003-2127-9568</orcidid></search><sort><creationdate>20171120</creationdate><title>A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters</title><author>Lima, Fabio ; Sharma, Upendra K. ; Grunenberg, Lars ; Saha, Debasmita ; Johannsen, Sandra ; Sedelmeier, Joerg ; Van der Eycken, Erik V. ; Ley, Steven V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2680-8f1ab56edd87bd60bd08ae10e7085f5f0ae1ce315914f92ff4a6589a8dae743</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Acids</topic><topic>Alkenes</topic><topic>Aromatic compounds</topic><topic>Boronsäuren</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Esters</topic><topic>Kreuzkupplungen</topic><topic>Lewis base</topic><topic>Lewis-Basen-Katalyse</topic><topic>Photoredoxkatalyse</topic><topic>Synthesemethoden</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lima, Fabio</creatorcontrib><creatorcontrib>Sharma, Upendra K.</creatorcontrib><creatorcontrib>Grunenberg, Lars</creatorcontrib><creatorcontrib>Saha, Debasmita</creatorcontrib><creatorcontrib>Johannsen, Sandra</creatorcontrib><creatorcontrib>Sedelmeier, Joerg</creatorcontrib><creatorcontrib>Van der Eycken, Erik V.</creatorcontrib><creatorcontrib>Ley, Steven V.</creatorcontrib><collection>Wiley-Blackwell Open Access Titles</collection><collection>Wiley Free Content</collection><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>Lima, Fabio</au><au>Sharma, Upendra K.</au><au>Grunenberg, Lars</au><au>Saha, Debasmita</au><au>Johannsen, Sandra</au><au>Sedelmeier, Joerg</au><au>Van der Eycken, Erik V.</au><au>Ley, Steven V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters</atitle><jtitle>Angewandte Chemie</jtitle><date>2017-11-20</date><risdate>2017</risdate><volume>129</volume><issue>47</issue><spage>15332</spage><epage>15336</epage><pages>15332-15336</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>We report herein the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin‐3‐ol or 4‐dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alkyl boronic acids to react with electron‐deficient olefins via radical addition to efficiently form C−C coupled products in a redox‐neutral fashion. The Lewis base catalyst was shown to form a redox‐active complex with either the boronic esters or the trimeric form of the boronic acids (boroxines) in solution.
Ein duales Katalysatorsystem bestehend aus einer Lewis‐Base (LB), z. B. Chinucludin‐3‐ol oder 4‐Dimethylaminopyridin, und einem Photoredoxkatalysator ermöglicht die Erzeugung von Kohlenstoffradikalen aus Boronsäuren und ‐estern. Verschiedene Alkylboronsäureester sowie Aryl‐ und Alkylboronsäuren reagieren mit elektronenarmen Olefinen in einem redoxneutralen Prozess zu C‐C‐Kupplungsprodukten.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.201709690</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-7816-0042</orcidid><orcidid>https://orcid.org/0000-0003-2127-9568</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Acids Alkenes Aromatic compounds Boronsäuren Catalysis Catalysts Chemistry Esters Kreuzkupplungen Lewis base Lewis-Basen-Katalyse Photoredoxkatalyse Synthesemethoden |
| title | A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters |
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