Copper-catalyzed stereoselective alkylhydrazination of alkynes
An unprecedented Cu-catalyzed stereoselective alkylhydrazination reaction involving terminal alkynes, azocarboxylic esters as a nitrogen source, and dimethyl 2,2′-azobis(2-methylpropionate) and its analogues as a carbon source is presented here. This protocol provides direct access to tri-substitute...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2020-01, Vol.56 (6), p.92-923 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Lei, Jian Gao, Huaxin Huang, Miaoling Liu, Xiao Mao, Yangfan Xie, Xiaolan |
| description | An unprecedented Cu-catalyzed stereoselective alkylhydrazination reaction involving terminal alkynes, azocarboxylic esters as a nitrogen source, and dimethyl 2,2′-azobis(2-methylpropionate) and its analogues as a carbon source is presented here. This protocol provides direct access to tri-substituted (
E
)-alkenyl-hydrazines with good regio- and stereoselectivity under mild conditions. The transformation proceeds without an external oxidant or additives and shows good functional group tolerance. The alkenylhydrazine products could be easily converted into valuable 1,4-dicarbonyl and allyl carboxylic derivatives.
An efficient copper-catalyzed stereoselective alkylhydrazination of alkynes, leading to tri-substituted (
E
)-alkenylhydrazines, has been developed. |
| doi_str_mv | 10.1039/c9cc07998j |
| format | Article |
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E
)-alkenyl-hydrazines with good regio- and stereoselectivity under mild conditions. The transformation proceeds without an external oxidant or additives and shows good functional group tolerance. The alkenylhydrazine products could be easily converted into valuable 1,4-dicarbonyl and allyl carboxylic derivatives.
An efficient copper-catalyzed stereoselective alkylhydrazination of alkynes, leading to tri-substituted (
E
)-alkenylhydrazines, has been developed.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c9cc07998j</identifier><identifier>PMID: 31850405</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Additives ; Alkynes ; Copper ; Crystallography ; Esters ; Functional groups ; Hydrazines ; Oxidizing agents ; Stereoselectivity</subject><ispartof>Chemical communications (Cambridge, England), 2020-01, Vol.56 (6), p.92-923</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c403t-25d2ce70533c1828debed65d865758f074025a9c47c625d7f75acac0a03425b03</citedby><cites>FETCH-LOGICAL-c403t-25d2ce70533c1828debed65d865758f074025a9c47c625d7f75acac0a03425b03</cites><orcidid>0000-0002-7617-2170</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31850405$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lei, Jian</creatorcontrib><creatorcontrib>Gao, Huaxin</creatorcontrib><creatorcontrib>Huang, Miaoling</creatorcontrib><creatorcontrib>Liu, Xiao</creatorcontrib><creatorcontrib>Mao, Yangfan</creatorcontrib><creatorcontrib>Xie, Xiaolan</creatorcontrib><title>Copper-catalyzed stereoselective alkylhydrazination of alkynes</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>An unprecedented Cu-catalyzed stereoselective alkylhydrazination reaction involving terminal alkynes, azocarboxylic esters as a nitrogen source, and dimethyl 2,2′-azobis(2-methylpropionate) and its analogues as a carbon source is presented here. This protocol provides direct access to tri-substituted (
E
)-alkenyl-hydrazines with good regio- and stereoselectivity under mild conditions. The transformation proceeds without an external oxidant or additives and shows good functional group tolerance. The alkenylhydrazine products could be easily converted into valuable 1,4-dicarbonyl and allyl carboxylic derivatives.
An efficient copper-catalyzed stereoselective alkylhydrazination of alkynes, leading to tri-substituted (
E
)-alkenylhydrazines, has been developed.</description><subject>Additives</subject><subject>Alkynes</subject><subject>Copper</subject><subject>Crystallography</subject><subject>Esters</subject><subject>Functional groups</subject><subject>Hydrazines</subject><subject>Oxidizing agents</subject><subject>Stereoselectivity</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpd0UtLxDAQB_AgiqurF-_KghcRqnk2yUWQ4pMFLwreSjadYtdusyat0P30Zh-uYC4zJD-G4R-ETgi-Ipjpa6utxVJrNd1BB4SlPBFcve8ue6ETybgYoMMQpjgeItQ-GjCiBOZYHKCbzM3n4BNrWlP3CyhGoQUPLkANtq2-YWTqz77-6AtvFlVj2so1I1eubhsIR2ivNHWA400dorf7u9fsMRm_PDxlt-PEcszahIqCWpBYMGaJoqqACRSpKFQqpFAllhxTYbTl0qbRylIKY43FBjNOxQSzIbpYz51799VBaPNZFSzUtWnAdSGnjCrGU4FJpOf_6NR1vonbRcUp0wRTGtXlWlnvQvBQ5nNfzYzvc4LzZap5prNslepzxGebkd1kBsWW_sYYweka-GC3r3_fwn4Adlh7Uw</recordid><startdate>20200118</startdate><enddate>20200118</enddate><creator>Lei, Jian</creator><creator>Gao, Huaxin</creator><creator>Huang, Miaoling</creator><creator>Liu, Xiao</creator><creator>Mao, Yangfan</creator><creator>Xie, Xiaolan</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7617-2170</orcidid></search><sort><creationdate>20200118</creationdate><title>Copper-catalyzed stereoselective alkylhydrazination of alkynes</title><author>Lei, Jian ; Gao, Huaxin ; Huang, Miaoling ; Liu, Xiao ; Mao, Yangfan ; Xie, Xiaolan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c403t-25d2ce70533c1828debed65d865758f074025a9c47c625d7f75acac0a03425b03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Additives</topic><topic>Alkynes</topic><topic>Copper</topic><topic>Crystallography</topic><topic>Esters</topic><topic>Functional groups</topic><topic>Hydrazines</topic><topic>Oxidizing agents</topic><topic>Stereoselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lei, Jian</creatorcontrib><creatorcontrib>Gao, Huaxin</creatorcontrib><creatorcontrib>Huang, Miaoling</creatorcontrib><creatorcontrib>Liu, Xiao</creatorcontrib><creatorcontrib>Mao, Yangfan</creatorcontrib><creatorcontrib>Xie, Xiaolan</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lei, Jian</au><au>Gao, Huaxin</au><au>Huang, Miaoling</au><au>Liu, Xiao</au><au>Mao, Yangfan</au><au>Xie, Xiaolan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-catalyzed stereoselective alkylhydrazination of alkynes</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2020-01-18</date><risdate>2020</risdate><volume>56</volume><issue>6</issue><spage>92</spage><epage>923</epage><pages>92-923</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>An unprecedented Cu-catalyzed stereoselective alkylhydrazination reaction involving terminal alkynes, azocarboxylic esters as a nitrogen source, and dimethyl 2,2′-azobis(2-methylpropionate) and its analogues as a carbon source is presented here. This protocol provides direct access to tri-substituted (
E
)-alkenyl-hydrazines with good regio- and stereoselectivity under mild conditions. The transformation proceeds without an external oxidant or additives and shows good functional group tolerance. The alkenylhydrazine products could be easily converted into valuable 1,4-dicarbonyl and allyl carboxylic derivatives.
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E
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| ispartof | Chemical communications (Cambridge, England), 2020-01, Vol.56 (6), p.92-923 |
| issn | 1359-7345 1364-548X |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Additives Alkynes Copper Crystallography Esters Functional groups Hydrazines Oxidizing agents Stereoselectivity |
| title | Copper-catalyzed stereoselective alkylhydrazination of alkynes |
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