Palladium‐Catalyzed Trifluoroethylation of Benzo[h]quinoline Derivatives by Mesityl(2,2,2‐trifluoroethyl)iodonium Triflate
Reactions of a dimeric [(bzq)Pd(OAc)]2 complex (1 a′) and mesityl(2,2,2‐trifluoroethyl)iodonium triflate (2 a) with or without additives at room temperature gave 10‐(2,2,2‐trifluoroethyl)benzo[h]quinoline rapidly in moderate to high yields. The reaction might proceed through a unstable binuclear “Pd...
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Veröffentlicht in: | Asian journal of organic chemistry 2019-05, Vol.8 (5), p.665-670 |
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description | Reactions of a dimeric [(bzq)Pd(OAc)]2 complex (1 a′) and mesityl(2,2,2‐trifluoroethyl)iodonium triflate (2 a) with or without additives at room temperature gave 10‐(2,2,2‐trifluoroethyl)benzo[h]quinoline rapidly in moderate to high yields. The reaction might proceed through a unstable binuclear “PdIII−CH2CF3” intermediate (I), which was likely formed in situ from the oxidative addition of 2 a to [(bzq)Pd(OAc)]2 and favorably transformed to mononuclear “(bzq)PdIV−CH2CF3” complexes (III) in the presence of another equiv.alent of 2 a and a suitable additive. Based on these, a Pd‐catalyzed C−H trifluoroethylation of benzo[h]quinolines with 2 a was developed. Numerous benzo[h]quinoline derivatives reacted with [MesICH2CF3][OTf] at room temperature in the presence of 10 mol% Pd(OAc)2 and 2 equiv.. NaHCO3 to provide the corresponding 10‐trifluoroethylated products in excellent yields.
Optional additive: A mild and convenient Pd‐catalyzed C−H trifluoroethylation of benzo[h]quinolines with mesityl(2,2,2‐trifluoroethyl)iodonium triflate was developed based on the stoichiometric reactions of a dimeric [(bzq)Pd(OAc)]2 complex and the triflate, which might proceed through an unstable binuclear “PdIII−CH2CF3” intermediate, likely formed in situ and favorably transformed to mononuclear “(bzq)PdIV−CH2CF3” complexes in the presence of an excess amount of the iodonium triflate and a suitable additive. |
doi_str_mv | 10.1002/ajoc.201900030 |
format | Article |
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Optional additive: A mild and convenient Pd‐catalyzed C−H trifluoroethylation of benzo[h]quinolines with mesityl(2,2,2‐trifluoroethyl)iodonium triflate was developed based on the stoichiometric reactions of a dimeric [(bzq)Pd(OAc)]2 complex and the triflate, which might proceed through an unstable binuclear “PdIII−CH2CF3” intermediate, likely formed in situ and favorably transformed to mononuclear “(bzq)PdIV−CH2CF3” complexes in the presence of an excess amount of the iodonium triflate and a suitable additive.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.201900030</identifier><language>eng</language><subject>benzo[h]quinolines ; C−H trifluoroethylation ; density functional calculations ; iodonium ; palladium</subject><ispartof>Asian journal of organic chemistry, 2019-05, Vol.8 (5), p.665-670</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3550-5a6bcf88b3785fbadcc300130f5ed5ab1b51b8eba0b792b6cdfbdca026f9f0943</citedby><cites>FETCH-LOGICAL-c3550-5a6bcf88b3785fbadcc300130f5ed5ab1b51b8eba0b792b6cdfbdca026f9f0943</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%2Fajoc.201900030$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.201900030$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids></links><search><creatorcontrib>Han, Qiu‐Yan</creatorcontrib><creatorcontrib>Hu, Xiaoxiao</creatorcontrib><creatorcontrib>Xue, Xiao‐Song</creatorcontrib><creatorcontrib>Zhao, Cheng‐Long</creatorcontrib><creatorcontrib>Zhang, Cheng‐Pan</creatorcontrib><title>Palladium‐Catalyzed Trifluoroethylation of Benzo[h]quinoline Derivatives by Mesityl(2,2,2‐trifluoroethyl)iodonium Triflate</title><title>Asian journal of organic chemistry</title><description>Reactions of a dimeric [(bzq)Pd(OAc)]2 complex (1 a′) and mesityl(2,2,2‐trifluoroethyl)iodonium triflate (2 a) with or without additives at room temperature gave 10‐(2,2,2‐trifluoroethyl)benzo[h]quinoline rapidly in moderate to high yields. The reaction might proceed through a unstable binuclear “PdIII−CH2CF3” intermediate (I), which was likely formed in situ from the oxidative addition of 2 a to [(bzq)Pd(OAc)]2 and favorably transformed to mononuclear “(bzq)PdIV−CH2CF3” complexes (III) in the presence of another equiv.alent of 2 a and a suitable additive. Based on these, a Pd‐catalyzed C−H trifluoroethylation of benzo[h]quinolines with 2 a was developed. Numerous benzo[h]quinoline derivatives reacted with [MesICH2CF3][OTf] at room temperature in the presence of 10 mol% Pd(OAc)2 and 2 equiv.. NaHCO3 to provide the corresponding 10‐trifluoroethylated products in excellent yields.
Optional additive: A mild and convenient Pd‐catalyzed C−H trifluoroethylation of benzo[h]quinolines with mesityl(2,2,2‐trifluoroethyl)iodonium triflate was developed based on the stoichiometric reactions of a dimeric [(bzq)Pd(OAc)]2 complex and the triflate, which might proceed through an unstable binuclear “PdIII−CH2CF3” intermediate, likely formed in situ and favorably transformed to mononuclear “(bzq)PdIV−CH2CF3” complexes in the presence of an excess amount of the iodonium triflate and a suitable additive.</description><subject>benzo[h]quinolines</subject><subject>C−H trifluoroethylation</subject><subject>density functional calculations</subject><subject>iodonium</subject><subject>palladium</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkM1Kw0AUhQdRsNRuXWepYOqdidNkljX-U6mLuhIJ80unTDOaSSvpQnwEn9EnMaVScSV3cS_cc74DB6FDDH0MQE75zMs-AcwAIIEd1CGYJTHNMN3d3pDuo14Is1YCacowYR30_sCd48ou5l8fnzmvuWtWWkWTyhq38JXX9bRxvLa-jLyJznW58k_T59eFLb2zpY4udGWX7X-pQySa6F4HWzfuiJy00xLrP5xj65Uv26wNn9f6AO0Z7oLu_ewuery6nOQ38Wh8fZsPR7FMKIWY8oGQJstEkmbUCK6kTABwAoZqRbnAgmKRacFBpIyIgVRGKMmBDAwzwM6SLupvuLLyIVTaFC-VnfOqKTAU6wKLdYHFtsDWwDaGN-t084-6GN6N81_vN9ulezc</recordid><startdate>201905</startdate><enddate>201905</enddate><creator>Han, Qiu‐Yan</creator><creator>Hu, Xiaoxiao</creator><creator>Xue, Xiao‐Song</creator><creator>Zhao, Cheng‐Long</creator><creator>Zhang, Cheng‐Pan</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201905</creationdate><title>Palladium‐Catalyzed Trifluoroethylation of Benzo[h]quinoline Derivatives by Mesityl(2,2,2‐trifluoroethyl)iodonium Triflate</title><author>Han, Qiu‐Yan ; Hu, Xiaoxiao ; Xue, Xiao‐Song ; Zhao, Cheng‐Long ; Zhang, Cheng‐Pan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3550-5a6bcf88b3785fbadcc300130f5ed5ab1b51b8eba0b792b6cdfbdca026f9f0943</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>benzo[h]quinolines</topic><topic>C−H trifluoroethylation</topic><topic>density functional calculations</topic><topic>iodonium</topic><topic>palladium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Han, Qiu‐Yan</creatorcontrib><creatorcontrib>Hu, Xiaoxiao</creatorcontrib><creatorcontrib>Xue, Xiao‐Song</creatorcontrib><creatorcontrib>Zhao, Cheng‐Long</creatorcontrib><creatorcontrib>Zhang, Cheng‐Pan</creatorcontrib><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Han, Qiu‐Yan</au><au>Hu, Xiaoxiao</au><au>Xue, Xiao‐Song</au><au>Zhao, Cheng‐Long</au><au>Zhang, Cheng‐Pan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium‐Catalyzed Trifluoroethylation of Benzo[h]quinoline Derivatives by Mesityl(2,2,2‐trifluoroethyl)iodonium Triflate</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2019-05</date><risdate>2019</risdate><volume>8</volume><issue>5</issue><spage>665</spage><epage>670</epage><pages>665-670</pages><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>Reactions of a dimeric [(bzq)Pd(OAc)]2 complex (1 a′) and mesityl(2,2,2‐trifluoroethyl)iodonium triflate (2 a) with or without additives at room temperature gave 10‐(2,2,2‐trifluoroethyl)benzo[h]quinoline rapidly in moderate to high yields. The reaction might proceed through a unstable binuclear “PdIII−CH2CF3” intermediate (I), which was likely formed in situ from the oxidative addition of 2 a to [(bzq)Pd(OAc)]2 and favorably transformed to mononuclear “(bzq)PdIV−CH2CF3” complexes (III) in the presence of another equiv.alent of 2 a and a suitable additive. Based on these, a Pd‐catalyzed C−H trifluoroethylation of benzo[h]quinolines with 2 a was developed. Numerous benzo[h]quinoline derivatives reacted with [MesICH2CF3][OTf] at room temperature in the presence of 10 mol% Pd(OAc)2 and 2 equiv.. NaHCO3 to provide the corresponding 10‐trifluoroethylated products in excellent yields.
Optional additive: A mild and convenient Pd‐catalyzed C−H trifluoroethylation of benzo[h]quinolines with mesityl(2,2,2‐trifluoroethyl)iodonium triflate was developed based on the stoichiometric reactions of a dimeric [(bzq)Pd(OAc)]2 complex and the triflate, which might proceed through an unstable binuclear “PdIII−CH2CF3” intermediate, likely formed in situ and favorably transformed to mononuclear “(bzq)PdIV−CH2CF3” complexes in the presence of an excess amount of the iodonium triflate and a suitable additive.</abstract><doi>10.1002/ajoc.201900030</doi><tpages>6</tpages></addata></record> |
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subjects | benzo[h]quinolines C−H trifluoroethylation density functional calculations iodonium palladium |
title | Palladium‐Catalyzed Trifluoroethylation of Benzo[h]quinoline Derivatives by Mesityl(2,2,2‐trifluoroethyl)iodonium Triflate |
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