Copper() reagent-promoted hydroxytrifluoromethylation of enamides: flexible synthesis of substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one
A novel CuBr-catalyzed hydroxytrifluoromethylation reaction was investigated. Substituted 3-benzylidene-2-arylisoindolin-1-ones was reacted with sodium trifluoromethanesulfinate to afford substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one. The reaction proceeded at 25 °C in...
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| Veröffentlicht in: | RSC advances 2018-07, Vol.8 (46), p.25961-25965 |
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| container_title | RSC advances |
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| creator | Wang, Qing Shi, Peng Zeng, Runsheng |
| description | A novel CuBr-catalyzed hydroxytrifluoromethylation reaction was investigated. Substituted 3-benzylidene-2-arylisoindolin-1-ones was reacted with sodium trifluoromethanesulfinate to afford substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one. The reaction proceeded at 25 °C in air atmosphere in the absence of base and ligands. Our results indicate that trifluoromethyl free radical tends to attack a double bond rather than aryl in this reaction.
A novel CuBr-catalyzed hydroxytrifluoromethylation reaction was investigated. Substituted 3-benzylidene-2-arylisoindolin-1-ones were reacted with sodium trifluoromethanesulfinate to afford substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one. |
| doi_str_mv | 10.1039/c8ra04088e |
| format | Article |
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A novel CuBr-catalyzed hydroxytrifluoromethylation reaction was investigated. Substituted 3-benzylidene-2-arylisoindolin-1-ones were reacted with sodium trifluoromethanesulfinate to afford substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/c8ra04088e</identifier><identifier>PMID: 35541984</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Chemical synthesis ; Chemistry ; Free radicals ; Reagents ; Substitutes</subject><ispartof>RSC advances, 2018-07, Vol.8 (46), p.25961-25965</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2018</rights><rights>This journal is © The Royal Society of Chemistry 2018 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c428t-23db2bff527011bf54a8ff49e71e6821f17208c92f1d8592a1a945b654d43ac13</citedby><cites>FETCH-LOGICAL-c428t-23db2bff527011bf54a8ff49e71e6821f17208c92f1d8592a1a945b654d43ac13</cites><orcidid>0000-0002-3655-3542</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9082868/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9082868/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35541984$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Qing</creatorcontrib><creatorcontrib>Shi, Peng</creatorcontrib><creatorcontrib>Zeng, Runsheng</creatorcontrib><title>Copper() reagent-promoted hydroxytrifluoromethylation of enamides: flexible synthesis of substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>A novel CuBr-catalyzed hydroxytrifluoromethylation reaction was investigated. Substituted 3-benzylidene-2-arylisoindolin-1-ones was reacted with sodium trifluoromethanesulfinate to afford substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one. The reaction proceeded at 25 °C in air atmosphere in the absence of base and ligands. Our results indicate that trifluoromethyl free radical tends to attack a double bond rather than aryl in this reaction.
A novel CuBr-catalyzed hydroxytrifluoromethylation reaction was investigated. Substituted 3-benzylidene-2-arylisoindolin-1-ones were reacted with sodium trifluoromethanesulfinate to afford substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one.</description><subject>Aromatic compounds</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Free radicals</subject><subject>Reagents</subject><subject>Substitutes</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpdkt1v1SAYxhujccvcjfeaJt6cGVGg0NJdmCwn8yNZYmL0mtD2ZYeFQgVq1j_I_1POh8cpXEDe55eHB3iL4jnBbwmu2ne9CAozLAQ8Kk4pZjWiuG4fP9ifFOcx3uE8ak5oTZ4WJxXnjLSCnRa_1n6aIKwuygDqFlxCU_CjTzCUm2UI_n5JwWg7-1yFtFmsSsa70usSnBrNAPGy1BbuTWehjItLG4gmbvU4dzGZNGcrVKGDGaJIhcXmwoq-yRMd3RHZKbszLkz0xg3eGpfL3sGz4olWNsL5YT0rvn-4_rb-hG6-fPy8vrpBPaMiIVoNHe205rTBhHSaMyW0Zi00BGpBiSYNxaJvqSaD4C1VRLWMdzVnA6tUT6qz4v3ed5q7EYY-v0dQVk7BjDmc9MrIfxVnNvLW_5QtFlTUIhusDgbB_5ghJjma2IO1yoGfo6R1TTnDOV5GX_2H3vk5uHw9SXHDCKlos6Ve76k--BgD6GMYguW2AeRafL3aNcB1hl8-jH9E_3x3Bl7sgRD7o_q3g6rfSR-4KQ</recordid><startdate>20180719</startdate><enddate>20180719</enddate><creator>Wang, Qing</creator><creator>Shi, Peng</creator><creator>Zeng, Runsheng</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-3655-3542</orcidid></search><sort><creationdate>20180719</creationdate><title>Copper() reagent-promoted hydroxytrifluoromethylation of enamides: flexible synthesis of substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one</title><author>Wang, Qing ; Shi, Peng ; Zeng, Runsheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c428t-23db2bff527011bf54a8ff49e71e6821f17208c92f1d8592a1a945b654d43ac13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aromatic compounds</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Free radicals</topic><topic>Reagents</topic><topic>Substitutes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Qing</creatorcontrib><creatorcontrib>Shi, Peng</creatorcontrib><creatorcontrib>Zeng, Runsheng</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Qing</au><au>Shi, Peng</au><au>Zeng, Runsheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper() reagent-promoted hydroxytrifluoromethylation of enamides: flexible synthesis of substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2018-07-19</date><risdate>2018</risdate><volume>8</volume><issue>46</issue><spage>25961</spage><epage>25965</epage><pages>25961-25965</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>A novel CuBr-catalyzed hydroxytrifluoromethylation reaction was investigated. Substituted 3-benzylidene-2-arylisoindolin-1-ones was reacted with sodium trifluoromethanesulfinate to afford substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one. The reaction proceeded at 25 °C in air atmosphere in the absence of base and ligands. Our results indicate that trifluoromethyl free radical tends to attack a double bond rather than aryl in this reaction.
A novel CuBr-catalyzed hydroxytrifluoromethylation reaction was investigated. Substituted 3-benzylidene-2-arylisoindolin-1-ones were reacted with sodium trifluoromethanesulfinate to afford substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>35541984</pmid><doi>10.1039/c8ra04088e</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-3655-3542</orcidid><oa>free_for_read</oa></addata></record> |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| subjects | Aromatic compounds Chemical synthesis Chemistry Free radicals Reagents Substitutes |
| title | Copper() reagent-promoted hydroxytrifluoromethylation of enamides: flexible synthesis of substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one |
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