Synthesis of Polysubstituted 2‐Naphthols by Palladium‐Catalyzed Intramolecular Arylation/Aromatization Cascade
A palladium‐catalyzed intramolecular α‐arylation and defluorinative aromatization strategy for the synthesis of polysubstituted 2‐naphthols is reported. With ortho‐bromobenzyl‐substituted α‐fluoroketones as the substrates and palladium acetate/triphenylphosphine as the catalyst, this method features...
Gespeichert in:
| Veröffentlicht in: | Advanced synthesis & catalysis 2020-03, Vol.362 (6), p.1303-1308 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1308 |
|---|---|
| container_issue | 6 |
| container_start_page | 1303 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 362 |
| creator | Cai, Jinhui Wang, Zhen‐Kai Zhang, Yun‐Hao Yao, Fei Hu, Xu‐Dong Liu, Wen‐Bo |
| description | A palladium‐catalyzed intramolecular α‐arylation and defluorinative aromatization strategy for the synthesis of polysubstituted 2‐naphthols is reported. With ortho‐bromobenzyl‐substituted α‐fluoroketones as the substrates and palladium acetate/triphenylphosphine as the catalyst, this method features good functional group tolerance, readily available catalyst and starting materials, and high yields. The applications of the strategy are demonstrated by the synthesis of useful building blocks, such as naphtha[2,3‐b]furan, naphthol AS‐D, and ligands/catalysts. |
| doi_str_mv | 10.1002/adsc.201901573 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2378197256</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2378197256</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3543-94bc2d2120604681e6d2acd0b2db0e0bebaa06aafa89e406e3195a5cd89dc5cf3</originalsourceid><addsrcrecordid>eNqFkM1OwzAQhCMEEqVw5RyJc1vbiZP4GIW_ShVUKpytje2oqZy42I5QeuIReEaehJSicuS0s9pvdqQJgmuMphghMgPpxJQgzBCmaXQSjHCC6STGCTs9aorOgwvnNgjhNEvTUWBXfevXytUuNFW4NLp3Xel87TuvZEi-Pj6fYLv2a6NdWPbhErQGWXfNcCjAg-53AzZvvYXGaCU6DTbMba_B16ad5dY0g9r9bGEBToBUl8FZBdqpq985Dl7v716Kx8ni-WFe5IuJiGgcTVhcCiIJJihBcZJhlUgCQqKSyBIpVKoSACUAFWRMxShREWYUqJAZk4KKKhoHN4e_W2veOuU835jOtkMkJ1GaYZYSmgzU9EAJa5yzquJbWzdge44R3_fK973yY6-DgR0M77VW_T80z29XxZ_3G7YqgYw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2378197256</pqid></control><display><type>article</type><title>Synthesis of Polysubstituted 2‐Naphthols by Palladium‐Catalyzed Intramolecular Arylation/Aromatization Cascade</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Cai, Jinhui ; Wang, Zhen‐Kai ; Zhang, Yun‐Hao ; Yao, Fei ; Hu, Xu‐Dong ; Liu, Wen‐Bo</creator><creatorcontrib>Cai, Jinhui ; Wang, Zhen‐Kai ; Zhang, Yun‐Hao ; Yao, Fei ; Hu, Xu‐Dong ; Liu, Wen‐Bo</creatorcontrib><description>A palladium‐catalyzed intramolecular α‐arylation and defluorinative aromatization strategy for the synthesis of polysubstituted 2‐naphthols is reported. With ortho‐bromobenzyl‐substituted α‐fluoroketones as the substrates and palladium acetate/triphenylphosphine as the catalyst, this method features good functional group tolerance, readily available catalyst and starting materials, and high yields. The applications of the strategy are demonstrated by the synthesis of useful building blocks, such as naphtha[2,3‐b]furan, naphthol AS‐D, and ligands/catalysts.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201901573</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>2-naphthol ; aromatization ; Catalysts ; cyclization ; C−C bond formation ; defluorination ; Functional groups ; Naphtha ; Naphthol ; Palladium ; Substrates</subject><ispartof>Advanced synthesis & catalysis, 2020-03, Vol.362 (6), p.1303-1308</ispartof><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3543-94bc2d2120604681e6d2acd0b2db0e0bebaa06aafa89e406e3195a5cd89dc5cf3</citedby><cites>FETCH-LOGICAL-c3543-94bc2d2120604681e6d2acd0b2db0e0bebaa06aafa89e406e3195a5cd89dc5cf3</cites></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.201901573$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201901573$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Cai, Jinhui</creatorcontrib><creatorcontrib>Wang, Zhen‐Kai</creatorcontrib><creatorcontrib>Zhang, Yun‐Hao</creatorcontrib><creatorcontrib>Yao, Fei</creatorcontrib><creatorcontrib>Hu, Xu‐Dong</creatorcontrib><creatorcontrib>Liu, Wen‐Bo</creatorcontrib><title>Synthesis of Polysubstituted 2‐Naphthols by Palladium‐Catalyzed Intramolecular Arylation/Aromatization Cascade</title><title>Advanced synthesis & catalysis</title><description>A palladium‐catalyzed intramolecular α‐arylation and defluorinative aromatization strategy for the synthesis of polysubstituted 2‐naphthols is reported. With ortho‐bromobenzyl‐substituted α‐fluoroketones as the substrates and palladium acetate/triphenylphosphine as the catalyst, this method features good functional group tolerance, readily available catalyst and starting materials, and high yields. The applications of the strategy are demonstrated by the synthesis of useful building blocks, such as naphtha[2,3‐b]furan, naphthol AS‐D, and ligands/catalysts.</description><subject>2-naphthol</subject><subject>aromatization</subject><subject>Catalysts</subject><subject>cyclization</subject><subject>C−C bond formation</subject><subject>defluorination</subject><subject>Functional groups</subject><subject>Naphtha</subject><subject>Naphthol</subject><subject>Palladium</subject><subject>Substrates</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkM1OwzAQhCMEEqVw5RyJc1vbiZP4GIW_ShVUKpytje2oqZy42I5QeuIReEaehJSicuS0s9pvdqQJgmuMphghMgPpxJQgzBCmaXQSjHCC6STGCTs9aorOgwvnNgjhNEvTUWBXfevXytUuNFW4NLp3Xel87TuvZEi-Pj6fYLv2a6NdWPbhErQGWXfNcCjAg-53AzZvvYXGaCU6DTbMba_B16ad5dY0g9r9bGEBToBUl8FZBdqpq985Dl7v716Kx8ni-WFe5IuJiGgcTVhcCiIJJihBcZJhlUgCQqKSyBIpVKoSACUAFWRMxShREWYUqJAZk4KKKhoHN4e_W2veOuU835jOtkMkJ1GaYZYSmgzU9EAJa5yzquJbWzdge44R3_fK973yY6-DgR0M77VW_T80z29XxZ_3G7YqgYw</recordid><startdate>20200317</startdate><enddate>20200317</enddate><creator>Cai, Jinhui</creator><creator>Wang, Zhen‐Kai</creator><creator>Zhang, Yun‐Hao</creator><creator>Yao, Fei</creator><creator>Hu, Xu‐Dong</creator><creator>Liu, Wen‐Bo</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20200317</creationdate><title>Synthesis of Polysubstituted 2‐Naphthols by Palladium‐Catalyzed Intramolecular Arylation/Aromatization Cascade</title><author>Cai, Jinhui ; Wang, Zhen‐Kai ; Zhang, Yun‐Hao ; Yao, Fei ; Hu, Xu‐Dong ; Liu, Wen‐Bo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3543-94bc2d2120604681e6d2acd0b2db0e0bebaa06aafa89e406e3195a5cd89dc5cf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>2-naphthol</topic><topic>aromatization</topic><topic>Catalysts</topic><topic>cyclization</topic><topic>C−C bond formation</topic><topic>defluorination</topic><topic>Functional groups</topic><topic>Naphtha</topic><topic>Naphthol</topic><topic>Palladium</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cai, Jinhui</creatorcontrib><creatorcontrib>Wang, Zhen‐Kai</creatorcontrib><creatorcontrib>Zhang, Yun‐Hao</creatorcontrib><creatorcontrib>Yao, Fei</creatorcontrib><creatorcontrib>Hu, Xu‐Dong</creatorcontrib><creatorcontrib>Liu, Wen‐Bo</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>Cai, Jinhui</au><au>Wang, Zhen‐Kai</au><au>Zhang, Yun‐Hao</au><au>Yao, Fei</au><au>Hu, Xu‐Dong</au><au>Liu, Wen‐Bo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Polysubstituted 2‐Naphthols by Palladium‐Catalyzed Intramolecular Arylation/Aromatization Cascade</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2020-03-17</date><risdate>2020</risdate><volume>362</volume><issue>6</issue><spage>1303</spage><epage>1308</epage><pages>1303-1308</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A palladium‐catalyzed intramolecular α‐arylation and defluorinative aromatization strategy for the synthesis of polysubstituted 2‐naphthols is reported. With ortho‐bromobenzyl‐substituted α‐fluoroketones as the substrates and palladium acetate/triphenylphosphine as the catalyst, this method features good functional group tolerance, readily available catalyst and starting materials, and high yields. The applications of the strategy are demonstrated by the synthesis of useful building blocks, such as naphtha[2,3‐b]furan, naphthol AS‐D, and ligands/catalysts.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201901573</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2020-03, Vol.362 (6), p.1303-1308 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_proquest_journals_2378197256 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | 2-naphthol aromatization Catalysts cyclization C−C bond formation defluorination Functional groups Naphtha Naphthol Palladium Substrates |
| title | Synthesis of Polysubstituted 2‐Naphthols by Palladium‐Catalyzed Intramolecular Arylation/Aromatization Cascade |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-08T00%3A05%3A21IST&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=Synthesis%20of%20Polysubstituted%202%E2%80%90Naphthols%20by%20Palladium%E2%80%90Catalyzed%20Intramolecular%20Arylation/Aromatization%20Cascade&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Cai,%20Jinhui&rft.date=2020-03-17&rft.volume=362&rft.issue=6&rft.spage=1303&rft.epage=1308&rft.pages=1303-1308&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201901573&rft_dat=%3Cproquest_cross%3E2378197256%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=2378197256&rft_id=info:pmid/&rfr_iscdi=true |