Palladium-catalyzed ionic liquid-accelerated oxidative annulation of acetylenic oximes with unactivated long-chain enols
A palladium-catalyzed ionic liquid-accelerated oxidative cascade annulation/functionalization of acetylenic oximes with unactivated long-chain enols under aerobic conditions was accomplished. This newly developed protocol provides the rapid and straightforward synthetic strategy for the assembly of...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2020-09, Vol.22 (17), p.5584-5588 |
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| container_end_page | 5588 |
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| container_issue | 17 |
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| container_title | Green chemistry : an international journal and green chemistry resource : GC |
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| creator | Hu, Miao Lin, Zidong Li, Jianxiao Wu, Wanqing Jiang, Huanfeng |
| description | A palladium-catalyzed ionic liquid-accelerated oxidative cascade annulation/functionalization of acetylenic oximes with unactivated long-chain enols under aerobic conditions was accomplished. This newly developed protocol provides the rapid and straightforward synthetic strategy for the assembly of structurally diverse isoxazole architectures under mild conditions with high atom- and step-economy and exceptional functional group tolerance. Notably, the ionic liquid acts as not only a solvent in the reaction but also provides the excess halide ions to eliminate hydrochloride from acetylenic oximes. Moreover, this catalytic system could be recycled up to eight times and reused without significant loss of the catalytic activity.
An NHC-palladium-catalyzed ionic liquid-accelerated oxidative annulation/functionalization with H
2
O or an ionic liquid as the medium was accomplished. |
| doi_str_mv | 10.1039/d0gc02037k |
| format | Article |
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An NHC-palladium-catalyzed ionic liquid-accelerated oxidative annulation/functionalization with H
2
O or an ionic liquid as the medium was accomplished.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/d0gc02037k</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Aerobic conditions ; Catalytic activity ; Chemical reactions ; Functional groups ; Green chemistry ; Ionic liquids ; Ions ; NMR ; Nuclear magnetic resonance ; Organic chemistry ; Oximes ; Palladium</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2020-09, Vol.22 (17), p.5584-5588</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c344t-e50909aac5b1d8a492eec43ce9fe8c650a2d4362627560c2994afecfdd9d7eb43</citedby><cites>FETCH-LOGICAL-c344t-e50909aac5b1d8a492eec43ce9fe8c650a2d4362627560c2994afecfdd9d7eb43</cites><orcidid>0000-0002-5246-5729 ; 0000-0002-4355-0294 ; 0000-0001-5151-7788</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Hu, Miao</creatorcontrib><creatorcontrib>Lin, Zidong</creatorcontrib><creatorcontrib>Li, Jianxiao</creatorcontrib><creatorcontrib>Wu, Wanqing</creatorcontrib><creatorcontrib>Jiang, Huanfeng</creatorcontrib><title>Palladium-catalyzed ionic liquid-accelerated oxidative annulation of acetylenic oximes with unactivated long-chain enols</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>A palladium-catalyzed ionic liquid-accelerated oxidative cascade annulation/functionalization of acetylenic oximes with unactivated long-chain enols under aerobic conditions was accomplished. This newly developed protocol provides the rapid and straightforward synthetic strategy for the assembly of structurally diverse isoxazole architectures under mild conditions with high atom- and step-economy and exceptional functional group tolerance. Notably, the ionic liquid acts as not only a solvent in the reaction but also provides the excess halide ions to eliminate hydrochloride from acetylenic oximes. Moreover, this catalytic system could be recycled up to eight times and reused without significant loss of the catalytic activity.
An NHC-palladium-catalyzed ionic liquid-accelerated oxidative annulation/functionalization with H
2
O or an ionic liquid as the medium was accomplished.</description><subject>Aerobic conditions</subject><subject>Catalytic activity</subject><subject>Chemical reactions</subject><subject>Functional groups</subject><subject>Green chemistry</subject><subject>Ionic liquids</subject><subject>Ions</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic chemistry</subject><subject>Oximes</subject><subject>Palladium</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kM1LxDAQxYMoqKsX70LFm1BNm_QjR1k_UdCDnsvsZKrRbLI2re761xt3RW-e5sH7vRnmMbaX8eOMC3Wi-RPynIvqdY1tZbIUqcorvv6ry3yTbYfwwnmWVaXcYvN7sBa0GaYpQg928Uk6Md4ZTKx5G4xOAZEsddBHw8-Nht68UwLODTZK7xLfJoDULyx9pyIypZB8mP45GRxgpJdR691Tis9gXELO27DDNlqwgXZ_5og9Xpw_jK_S27vL6_HpbYpCyj6lgiuuALCYZLoGqXIilAJJtVRjWXDItRRlfKwqSo65UhJawlZrpSuaSDFih6u9s86_DRT65sUPnYsnm1yKuogt1HmkjlYUdj6Ejtpm1pkpdIsm4813s80Zvxwvm72J8P4K7gL-cn_NR__gP7-Z6VZ8AcY-hAk</recordid><startdate>20200907</startdate><enddate>20200907</enddate><creator>Hu, Miao</creator><creator>Lin, Zidong</creator><creator>Li, Jianxiao</creator><creator>Wu, Wanqing</creator><creator>Jiang, Huanfeng</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U6</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0002-5246-5729</orcidid><orcidid>https://orcid.org/0000-0002-4355-0294</orcidid><orcidid>https://orcid.org/0000-0001-5151-7788</orcidid></search><sort><creationdate>20200907</creationdate><title>Palladium-catalyzed ionic liquid-accelerated oxidative annulation of acetylenic oximes with unactivated long-chain enols</title><author>Hu, Miao ; Lin, Zidong ; Li, Jianxiao ; Wu, Wanqing ; Jiang, Huanfeng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c344t-e50909aac5b1d8a492eec43ce9fe8c650a2d4362627560c2994afecfdd9d7eb43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aerobic conditions</topic><topic>Catalytic activity</topic><topic>Chemical reactions</topic><topic>Functional groups</topic><topic>Green chemistry</topic><topic>Ionic liquids</topic><topic>Ions</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic chemistry</topic><topic>Oximes</topic><topic>Palladium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hu, Miao</creatorcontrib><creatorcontrib>Lin, Zidong</creatorcontrib><creatorcontrib>Li, Jianxiao</creatorcontrib><creatorcontrib>Wu, Wanqing</creatorcontrib><creatorcontrib>Jiang, Huanfeng</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Materials Research Database</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hu, Miao</au><au>Lin, Zidong</au><au>Li, Jianxiao</au><au>Wu, Wanqing</au><au>Jiang, Huanfeng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-catalyzed ionic liquid-accelerated oxidative annulation of acetylenic oximes with unactivated long-chain enols</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2020-09-07</date><risdate>2020</risdate><volume>22</volume><issue>17</issue><spage>5584</spage><epage>5588</epage><pages>5584-5588</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>A palladium-catalyzed ionic liquid-accelerated oxidative cascade annulation/functionalization of acetylenic oximes with unactivated long-chain enols under aerobic conditions was accomplished. This newly developed protocol provides the rapid and straightforward synthetic strategy for the assembly of structurally diverse isoxazole architectures under mild conditions with high atom- and step-economy and exceptional functional group tolerance. Notably, the ionic liquid acts as not only a solvent in the reaction but also provides the excess halide ions to eliminate hydrochloride from acetylenic oximes. Moreover, this catalytic system could be recycled up to eight times and reused without significant loss of the catalytic activity.
An NHC-palladium-catalyzed ionic liquid-accelerated oxidative annulation/functionalization with H
2
O or an ionic liquid as the medium was accomplished.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d0gc02037k</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-5246-5729</orcidid><orcidid>https://orcid.org/0000-0002-4355-0294</orcidid><orcidid>https://orcid.org/0000-0001-5151-7788</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2020-09, Vol.22 (17), p.5584-5588 |
| issn | 1463-9262 1463-9270 |
| language | eng |
| recordid | cdi_rsc_primary_d0gc02037k |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aerobic conditions Catalytic activity Chemical reactions Functional groups Green chemistry Ionic liquids Ions NMR Nuclear magnetic resonance Organic chemistry Oximes Palladium |
| title | Palladium-catalyzed ionic liquid-accelerated oxidative annulation of acetylenic oximes with unactivated long-chain enols |
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