Defluorinative Alkylboration of Alkenes Enabled by Dual Photoredox and Copper Catalysis
A regioselectivity reversed three‐component defluorinative alkylboration of alkenes with trifluoromethyls and bis(pinacolato)diboron via dual photoredox/copper catalysis is reported. The mild conditions are compatible with a wide array of nonactivated trifluoromethyl aromatics bearing electron‐donat...
Gespeichert in:
| Veröffentlicht in: | Angewandte Chemie 2024-01, Vol.136 (5), p.n/a |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | n/a |
|---|---|
| container_issue | 5 |
| container_start_page | |
| container_title | Angewandte Chemie |
| container_volume | 136 |
| creator | Fan, Yanmin Huang, Zhonghou Lu, Yi Zhu, Shengqing Chu, Lingling |
| description | A regioselectivity reversed three‐component defluorinative alkylboration of alkenes with trifluoromethyls and bis(pinacolato)diboron via dual photoredox/copper catalysis is reported. The mild conditions are compatible with a wide array of nonactivated trifluoromethyl aromatics bearing electron‐donating or electron‐neutral substituents, trifluoroacetamides, and various nonactivated terminal and internal alkenes, enabling straightforward access to synthetically valuable γ‐gem‐difluoroalkyl boronates with high efficiency. Furthermore, this protocol is applicable to alkene‐tethered trifluoromethyl aromatics to furnish gem‐difluoromethylene‐containing cyclic compounds. Synthetic applications and preliminary mechanistic studies are also presented.
Reported here is a radical‐based three‐component defluorinative alkylboration of alkenes with trifluoromethyls and bis(pinacolato)diboron via dual photoredox/copper catalysis. This protocol offers efficient access to synthetically valuable γ‐gem‐difluoroalkyl boronates with high efficiency and reversed regioselectivity. |
| doi_str_mv | 10.1002/ange.202315974 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2916213230</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2916213230</sourcerecordid><originalsourceid>FETCH-LOGICAL-c1174-edce8e688e3a8fb9807f750e8d04762149a0329a77e30585e171ab8144c821b73</originalsourceid><addsrcrecordid>eNqFkD1PwzAQhi0EEqWwMltiTvFXanus0lKQKmAAMVpOcoEUEwc7AfLvSVUEI9PpTs_7nvQgdE7JjBLCLm3zDDNGGKepluIATWjKaMJlKg_RhBAhEsWEPkYnMW4JIXMm9QQ9LaFyvQ91Y7v6A_DCvQ4u92HcfIN9tTtAAxGvGps7KHE-4GVvHb5_8Z0PUPovbJsSZ75tIeDMdtYNsY6n6KiyLsLZz5yix6vVQ3adbO7WN9likxSUSpFAWYCCuVLArapyrYisZEpAlUTIOaNCW8KZtlICJ6lKgUpqc0WFKBSjueRTdLHvbYN_7yF2Zuv70IwvDdN0bOCMk5Ga7aki-BgDVKYN9ZsNg6HE7OSZnTzzK28M6H3gs3Yw_EObxe169Zf9BsRRcrI</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2916213230</pqid></control><display><type>article</type><title>Defluorinative Alkylboration of Alkenes Enabled by Dual Photoredox and Copper Catalysis</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Fan, Yanmin ; Huang, Zhonghou ; Lu, Yi ; Zhu, Shengqing ; Chu, Lingling</creator><creatorcontrib>Fan, Yanmin ; Huang, Zhonghou ; Lu, Yi ; Zhu, Shengqing ; Chu, Lingling</creatorcontrib><description>A regioselectivity reversed three‐component defluorinative alkylboration of alkenes with trifluoromethyls and bis(pinacolato)diboron via dual photoredox/copper catalysis is reported. The mild conditions are compatible with a wide array of nonactivated trifluoromethyl aromatics bearing electron‐donating or electron‐neutral substituents, trifluoroacetamides, and various nonactivated terminal and internal alkenes, enabling straightforward access to synthetically valuable γ‐gem‐difluoroalkyl boronates with high efficiency. Furthermore, this protocol is applicable to alkene‐tethered trifluoromethyl aromatics to furnish gem‐difluoromethylene‐containing cyclic compounds. Synthetic applications and preliminary mechanistic studies are also presented.
Reported here is a radical‐based three‐component defluorinative alkylboration of alkenes with trifluoromethyls and bis(pinacolato)diboron via dual photoredox/copper catalysis. This protocol offers efficient access to synthetically valuable γ‐gem‐difluoroalkyl boronates with high efficiency and reversed regioselectivity.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.202315974</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkenes ; Aromatic compounds ; Carboboration ; Catalysis ; Chemistry ; Copper ; Cyclic compounds ; Defluorination ; Photochemistry ; Regioselectivity</subject><ispartof>Angewandte Chemie, 2024-01, Vol.136 (5), p.n/a</ispartof><rights>2023 Wiley‐VCH GmbH</rights><rights>2024 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c1174-edce8e688e3a8fb9807f750e8d04762149a0329a77e30585e171ab8144c821b73</cites><orcidid>0000-0001-7969-0531</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.202315974$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.202315974$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids></links><search><creatorcontrib>Fan, Yanmin</creatorcontrib><creatorcontrib>Huang, Zhonghou</creatorcontrib><creatorcontrib>Lu, Yi</creatorcontrib><creatorcontrib>Zhu, Shengqing</creatorcontrib><creatorcontrib>Chu, Lingling</creatorcontrib><title>Defluorinative Alkylboration of Alkenes Enabled by Dual Photoredox and Copper Catalysis</title><title>Angewandte Chemie</title><description>A regioselectivity reversed three‐component defluorinative alkylboration of alkenes with trifluoromethyls and bis(pinacolato)diboron via dual photoredox/copper catalysis is reported. The mild conditions are compatible with a wide array of nonactivated trifluoromethyl aromatics bearing electron‐donating or electron‐neutral substituents, trifluoroacetamides, and various nonactivated terminal and internal alkenes, enabling straightforward access to synthetically valuable γ‐gem‐difluoroalkyl boronates with high efficiency. Furthermore, this protocol is applicable to alkene‐tethered trifluoromethyl aromatics to furnish gem‐difluoromethylene‐containing cyclic compounds. Synthetic applications and preliminary mechanistic studies are also presented.
Reported here is a radical‐based three‐component defluorinative alkylboration of alkenes with trifluoromethyls and bis(pinacolato)diboron via dual photoredox/copper catalysis. This protocol offers efficient access to synthetically valuable γ‐gem‐difluoroalkyl boronates with high efficiency and reversed regioselectivity.</description><subject>Alkenes</subject><subject>Aromatic compounds</subject><subject>Carboboration</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Copper</subject><subject>Cyclic compounds</subject><subject>Defluorination</subject><subject>Photochemistry</subject><subject>Regioselectivity</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkD1PwzAQhi0EEqWwMltiTvFXanus0lKQKmAAMVpOcoEUEwc7AfLvSVUEI9PpTs_7nvQgdE7JjBLCLm3zDDNGGKepluIATWjKaMJlKg_RhBAhEsWEPkYnMW4JIXMm9QQ9LaFyvQ91Y7v6A_DCvQ4u92HcfIN9tTtAAxGvGps7KHE-4GVvHb5_8Z0PUPovbJsSZ75tIeDMdtYNsY6n6KiyLsLZz5yix6vVQ3adbO7WN9likxSUSpFAWYCCuVLArapyrYisZEpAlUTIOaNCW8KZtlICJ6lKgUpqc0WFKBSjueRTdLHvbYN_7yF2Zuv70IwvDdN0bOCMk5Ga7aki-BgDVKYN9ZsNg6HE7OSZnTzzK28M6H3gs3Yw_EObxe169Zf9BsRRcrI</recordid><startdate>20240125</startdate><enddate>20240125</enddate><creator>Fan, Yanmin</creator><creator>Huang, Zhonghou</creator><creator>Lu, Yi</creator><creator>Zhu, Shengqing</creator><creator>Chu, Lingling</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/0000-0001-7969-0531</orcidid></search><sort><creationdate>20240125</creationdate><title>Defluorinative Alkylboration of Alkenes Enabled by Dual Photoredox and Copper Catalysis</title><author>Fan, Yanmin ; Huang, Zhonghou ; Lu, Yi ; Zhu, Shengqing ; Chu, Lingling</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1174-edce8e688e3a8fb9807f750e8d04762149a0329a77e30585e171ab8144c821b73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alkenes</topic><topic>Aromatic compounds</topic><topic>Carboboration</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Copper</topic><topic>Cyclic compounds</topic><topic>Defluorination</topic><topic>Photochemistry</topic><topic>Regioselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fan, Yanmin</creatorcontrib><creatorcontrib>Huang, Zhonghou</creatorcontrib><creatorcontrib>Lu, Yi</creatorcontrib><creatorcontrib>Zhu, Shengqing</creatorcontrib><creatorcontrib>Chu, Lingling</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>Fan, Yanmin</au><au>Huang, Zhonghou</au><au>Lu, Yi</au><au>Zhu, Shengqing</au><au>Chu, Lingling</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Defluorinative Alkylboration of Alkenes Enabled by Dual Photoredox and Copper Catalysis</atitle><jtitle>Angewandte Chemie</jtitle><date>2024-01-25</date><risdate>2024</risdate><volume>136</volume><issue>5</issue><epage>n/a</epage><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>A regioselectivity reversed three‐component defluorinative alkylboration of alkenes with trifluoromethyls and bis(pinacolato)diboron via dual photoredox/copper catalysis is reported. The mild conditions are compatible with a wide array of nonactivated trifluoromethyl aromatics bearing electron‐donating or electron‐neutral substituents, trifluoroacetamides, and various nonactivated terminal and internal alkenes, enabling straightforward access to synthetically valuable γ‐gem‐difluoroalkyl boronates with high efficiency. Furthermore, this protocol is applicable to alkene‐tethered trifluoromethyl aromatics to furnish gem‐difluoromethylene‐containing cyclic compounds. Synthetic applications and preliminary mechanistic studies are also presented.
Reported here is a radical‐based three‐component defluorinative alkylboration of alkenes with trifluoromethyls and bis(pinacolato)diboron via dual photoredox/copper catalysis. This protocol offers efficient access to synthetically valuable γ‐gem‐difluoroalkyl boronates with high efficiency and reversed regioselectivity.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ange.202315974</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-7969-0531</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0044-8249 |
| ispartof | Angewandte Chemie, 2024-01, Vol.136 (5), p.n/a |
| issn | 0044-8249 1521-3757 |
| language | eng |
| recordid | cdi_proquest_journals_2916213230 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkenes Aromatic compounds Carboboration Catalysis Chemistry Copper Cyclic compounds Defluorination Photochemistry Regioselectivity |
| title | Defluorinative Alkylboration of Alkenes Enabled by Dual Photoredox and Copper Catalysis |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-19T16%3A51%3A09IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Defluorinative%20Alkylboration%20of%20Alkenes%20Enabled%20by%20Dual%20Photoredox%20and%20Copper%20Catalysis&rft.jtitle=Angewandte%20Chemie&rft.au=Fan,%20Yanmin&rft.date=2024-01-25&rft.volume=136&rft.issue=5&rft.epage=n/a&rft.issn=0044-8249&rft.eissn=1521-3757&rft_id=info:doi/10.1002/ange.202315974&rft_dat=%3Cproquest_cross%3E2916213230%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2916213230&rft_id=info:pmid/&rfr_iscdi=true |