N,N’‐Difluoro‐2,2’‐bipyridinium Bis(tetrafluoroborate): a New Terminal Oxidant for Iodoarene‐catalyzed Fluorination Reactions
A new N−F reagent, N,N′‐difluoro‐2,2′‐bipyridinium bis(tetrafluoroborate), for iodoarene‐catalyzed fluorination reactions as a terminal oxidant is reported. This reaction is effective for the fluorination of simple alkenes, aromatic alkenes and 1,3‐dicarbonyl compounds, giving 1,2‐difluorinated alka...
Gespeichert in:
| Veröffentlicht in: | Advanced synthesis & catalysis 2023-08, Vol.365 (16), p.2744-2750 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2750 |
|---|---|
| container_issue | 16 |
| container_start_page | 2744 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 365 |
| creator | Kitamura, Tsugio Kitamura, Daichi Oyamada, Juzo Higashi, Masahiro Kishikawa, Yosuke |
| description | A new N−F reagent, N,N′‐difluoro‐2,2′‐bipyridinium bis(tetrafluoroborate), for iodoarene‐catalyzed fluorination reactions as a terminal oxidant is reported. This reaction is effective for the fluorination of simple alkenes, aromatic alkenes and 1,3‐dicarbonyl compounds, giving 1,2‐difluorinated alkanes, geminal difluorinated compounds, 2‐fluorinated‐1,3‐dicarbonyl compounds in good to high yields, respectively. This is a useful fluorination reaction that not only improves the issues of the fluorination reaction using conventional mCPBA as a terminal oxidant but also constructs a simpler catalytic cycle. The present N−F reagent can be recovered as 2,2’‐bipyridine. |
| doi_str_mv | 10.1002/adsc.202300265 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2854919433</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2854919433</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3175-5792faaed477ab344738be2e45621fb2cb1e8ee8eefd7d0e77f745deb75cac9b3</originalsourceid><addsrcrecordid>eNqFkEFLw0AQhYMoWKtXzwteFJq6u8lmG2-1tVooLWg9h012AlvSbN1NqPHUqzev_r3-EhMi9SgMzJvhe8PwHOeS4D7BmN4KaZM-xdSrh4AdOR0SEOb6JAiPD5rhU-fM2hXGhA847zif8958v_ve777GKs1KbXQtaY-2u1htKqOkylW5RvfKXhdQGNFysTaigJs7JNActmgJZq1ykaHFu5IiL1CqDZpqqYWBHOpbiShEVn2ARJPGX7OF0jl6BpE0wp47J6nILFz89q7zOnlYjp7c2eJxOhrO3MQjnLmMhzQVAqTPuYg93-feIAYKPgsoSWOaxAQG0FQqucTAecp9JiHmLBFJGHtd56q9uzH6rQRbRCtdmvpzG9EB80MS-p5XU_2WSoy21kAabYxaC1NFBEdN3FETd3SIuzaErWGrMqj-oaPh-GX05_0BGcqMqw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2854919433</pqid></control><display><type>article</type><title>N,N’‐Difluoro‐2,2’‐bipyridinium Bis(tetrafluoroborate): a New Terminal Oxidant for Iodoarene‐catalyzed Fluorination Reactions</title><source>Wiley Journals</source><creator>Kitamura, Tsugio ; Kitamura, Daichi ; Oyamada, Juzo ; Higashi, Masahiro ; Kishikawa, Yosuke</creator><creatorcontrib>Kitamura, Tsugio ; Kitamura, Daichi ; Oyamada, Juzo ; Higashi, Masahiro ; Kishikawa, Yosuke</creatorcontrib><description>A new N−F reagent, N,N′‐difluoro‐2,2′‐bipyridinium bis(tetrafluoroborate), for iodoarene‐catalyzed fluorination reactions as a terminal oxidant is reported. This reaction is effective for the fluorination of simple alkenes, aromatic alkenes and 1,3‐dicarbonyl compounds, giving 1,2‐difluorinated alkanes, geminal difluorinated compounds, 2‐fluorinated‐1,3‐dicarbonyl compounds in good to high yields, respectively. This is a useful fluorination reaction that not only improves the issues of the fluorination reaction using conventional mCPBA as a terminal oxidant but also constructs a simpler catalytic cycle. The present N−F reagent can be recovered as 2,2’‐bipyridine.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202300265</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Alkanes ; Alkenes ; Carbonyl compounds ; Catalysis ; Chemical reactions ; Fluorination ; Fluorine ; Iodine ; Oxidizing agents ; Reagents ; Recovery</subject><ispartof>Advanced synthesis & catalysis, 2023-08, Vol.365 (16), p.2744-2750</ispartof><rights>2023 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3175-5792faaed477ab344738be2e45621fb2cb1e8ee8eefd7d0e77f745deb75cac9b3</citedby><cites>FETCH-LOGICAL-c3175-5792faaed477ab344738be2e45621fb2cb1e8ee8eefd7d0e77f745deb75cac9b3</cites><orcidid>0000-0001-5592-5228</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%2Fadsc.202300265$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202300265$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Kitamura, Tsugio</creatorcontrib><creatorcontrib>Kitamura, Daichi</creatorcontrib><creatorcontrib>Oyamada, Juzo</creatorcontrib><creatorcontrib>Higashi, Masahiro</creatorcontrib><creatorcontrib>Kishikawa, Yosuke</creatorcontrib><title>N,N’‐Difluoro‐2,2’‐bipyridinium Bis(tetrafluoroborate): a New Terminal Oxidant for Iodoarene‐catalyzed Fluorination Reactions</title><title>Advanced synthesis & catalysis</title><description>A new N−F reagent, N,N′‐difluoro‐2,2′‐bipyridinium bis(tetrafluoroborate), for iodoarene‐catalyzed fluorination reactions as a terminal oxidant is reported. This reaction is effective for the fluorination of simple alkenes, aromatic alkenes and 1,3‐dicarbonyl compounds, giving 1,2‐difluorinated alkanes, geminal difluorinated compounds, 2‐fluorinated‐1,3‐dicarbonyl compounds in good to high yields, respectively. This is a useful fluorination reaction that not only improves the issues of the fluorination reaction using conventional mCPBA as a terminal oxidant but also constructs a simpler catalytic cycle. The present N−F reagent can be recovered as 2,2’‐bipyridine.</description><subject>Alkanes</subject><subject>Alkenes</subject><subject>Carbonyl compounds</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Fluorination</subject><subject>Fluorine</subject><subject>Iodine</subject><subject>Oxidizing agents</subject><subject>Reagents</subject><subject>Recovery</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkEFLw0AQhYMoWKtXzwteFJq6u8lmG2-1tVooLWg9h012AlvSbN1NqPHUqzev_r3-EhMi9SgMzJvhe8PwHOeS4D7BmN4KaZM-xdSrh4AdOR0SEOb6JAiPD5rhU-fM2hXGhA847zif8958v_ve777GKs1KbXQtaY-2u1htKqOkylW5RvfKXhdQGNFysTaigJs7JNActmgJZq1ykaHFu5IiL1CqDZpqqYWBHOpbiShEVn2ARJPGX7OF0jl6BpE0wp47J6nILFz89q7zOnlYjp7c2eJxOhrO3MQjnLmMhzQVAqTPuYg93-feIAYKPgsoSWOaxAQG0FQqucTAecp9JiHmLBFJGHtd56q9uzH6rQRbRCtdmvpzG9EB80MS-p5XU_2WSoy21kAabYxaC1NFBEdN3FETd3SIuzaErWGrMqj-oaPh-GX05_0BGcqMqw</recordid><startdate>20230815</startdate><enddate>20230815</enddate><creator>Kitamura, Tsugio</creator><creator>Kitamura, Daichi</creator><creator>Oyamada, Juzo</creator><creator>Higashi, Masahiro</creator><creator>Kishikawa, Yosuke</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-5592-5228</orcidid></search><sort><creationdate>20230815</creationdate><title>N,N’‐Difluoro‐2,2’‐bipyridinium Bis(tetrafluoroborate): a New Terminal Oxidant for Iodoarene‐catalyzed Fluorination Reactions</title><author>Kitamura, Tsugio ; Kitamura, Daichi ; Oyamada, Juzo ; Higashi, Masahiro ; Kishikawa, Yosuke</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3175-5792faaed477ab344738be2e45621fb2cb1e8ee8eefd7d0e77f745deb75cac9b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Alkanes</topic><topic>Alkenes</topic><topic>Carbonyl compounds</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Fluorination</topic><topic>Fluorine</topic><topic>Iodine</topic><topic>Oxidizing agents</topic><topic>Reagents</topic><topic>Recovery</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kitamura, Tsugio</creatorcontrib><creatorcontrib>Kitamura, Daichi</creatorcontrib><creatorcontrib>Oyamada, Juzo</creatorcontrib><creatorcontrib>Higashi, Masahiro</creatorcontrib><creatorcontrib>Kishikawa, Yosuke</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kitamura, Tsugio</au><au>Kitamura, Daichi</au><au>Oyamada, Juzo</au><au>Higashi, Masahiro</au><au>Kishikawa, Yosuke</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N,N’‐Difluoro‐2,2’‐bipyridinium Bis(tetrafluoroborate): a New Terminal Oxidant for Iodoarene‐catalyzed Fluorination Reactions</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2023-08-15</date><risdate>2023</risdate><volume>365</volume><issue>16</issue><spage>2744</spage><epage>2750</epage><pages>2744-2750</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A new N−F reagent, N,N′‐difluoro‐2,2′‐bipyridinium bis(tetrafluoroborate), for iodoarene‐catalyzed fluorination reactions as a terminal oxidant is reported. This reaction is effective for the fluorination of simple alkenes, aromatic alkenes and 1,3‐dicarbonyl compounds, giving 1,2‐difluorinated alkanes, geminal difluorinated compounds, 2‐fluorinated‐1,3‐dicarbonyl compounds in good to high yields, respectively. This is a useful fluorination reaction that not only improves the issues of the fluorination reaction using conventional mCPBA as a terminal oxidant but also constructs a simpler catalytic cycle. The present N−F reagent can be recovered as 2,2’‐bipyridine.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202300265</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-5592-5228</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2023-08, Vol.365 (16), p.2744-2750 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_proquest_journals_2854919433 |
| source | Wiley Journals |
| subjects | Alkanes Alkenes Carbonyl compounds Catalysis Chemical reactions Fluorination Fluorine Iodine Oxidizing agents Reagents Recovery |
| title | N,N’‐Difluoro‐2,2’‐bipyridinium Bis(tetrafluoroborate): a New Terminal Oxidant for Iodoarene‐catalyzed Fluorination Reactions |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T05%3A05%3A25IST&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=N,N%E2%80%99%E2%80%90Difluoro%E2%80%902,2%E2%80%99%E2%80%90bipyridinium%20Bis(tetrafluoroborate):%20a%20New%20Terminal%20Oxidant%20for%20Iodoarene%E2%80%90catalyzed%20Fluorination%20Reactions&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Kitamura,%20Tsugio&rft.date=2023-08-15&rft.volume=365&rft.issue=16&rft.spage=2744&rft.epage=2750&rft.pages=2744-2750&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.202300265&rft_dat=%3Cproquest_cross%3E2854919433%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=2854919433&rft_id=info:pmid/&rfr_iscdi=true |