Efficient E-Selective Transfer Semihydrogenation of Alkynes by Means of Ligand-Metal Cooperating Ruthenium Catalyst
The manuscript describes an efficient protocol for the E‐selective transfer semihydrogenation of internal alkynes employing a previously described bifunctional ruthenium‐based PC(sp3)P complex, 20 mol% of sodium formate and nearly stoichiometric formic acid. Semihydrogenation of the terminal alkynes...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2015-07, Vol.357 (10), p.2351-2357 |
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| container_issue | 10 |
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| container_title | Advanced synthesis & catalysis |
| container_volume | 357 |
| creator | Musa, Sanaa Ghosh, Amrita Vaccaro, Luigi Ackermann, Lutz Gelman, Dmitri |
| description | The manuscript describes an efficient protocol for the E‐selective transfer semihydrogenation of internal alkynes employing a previously described bifunctional ruthenium‐based PC(sp3)P complex, 20 mol% of sodium formate and nearly stoichiometric formic acid. Semihydrogenation of the terminal alkynes results in the formation of the corresponding styrenes. The mechanism of the reaction includes stepwise transfer of both the hydride and the proton of the formic acid to the substrate. This fact allowed for the development of a facile protocol for the synthesis of monodeuterated alkenes by simply applying formic acid/sodium formate/D2O mixture as a hydrogen source. High yields, selectivity and functional group compatibility have been generally achieved. |
| doi_str_mv | 10.1002/adsc.201500372 |
| format | Article |
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Semihydrogenation of the terminal alkynes results in the formation of the corresponding styrenes. The mechanism of the reaction includes stepwise transfer of both the hydride and the proton of the formic acid to the substrate. This fact allowed for the development of a facile protocol for the synthesis of monodeuterated alkenes by simply applying formic acid/sodium formate/D2O mixture as a hydrogen source. High yields, selectivity and functional group compatibility have been generally achieved.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201500372</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkenes ; Alkynes ; Catalysts ; Formates ; Formic acid ; isotope labelling ; ligand-metal cooperation ; ruthenium ; semihydrogenation of alkynes ; Sodium ; Styrenes ; Synthesis ; transfer hydrogenation</subject><ispartof>Advanced synthesis & catalysis, 2015-07, Vol.357 (10), p.2351-2357</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. 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Synth. Catal</addtitle><description>The manuscript describes an efficient protocol for the E‐selective transfer semihydrogenation of internal alkynes employing a previously described bifunctional ruthenium‐based PC(sp3)P complex, 20 mol% of sodium formate and nearly stoichiometric formic acid. Semihydrogenation of the terminal alkynes results in the formation of the corresponding styrenes. The mechanism of the reaction includes stepwise transfer of both the hydride and the proton of the formic acid to the substrate. This fact allowed for the development of a facile protocol for the synthesis of monodeuterated alkenes by simply applying formic acid/sodium formate/D2O mixture as a hydrogen source. High yields, selectivity and functional group compatibility have been generally achieved.</description><subject>Alkenes</subject><subject>Alkynes</subject><subject>Catalysts</subject><subject>Formates</subject><subject>Formic acid</subject><subject>isotope labelling</subject><subject>ligand-metal cooperation</subject><subject>ruthenium</subject><subject>semihydrogenation of alkynes</subject><subject>Sodium</subject><subject>Styrenes</subject><subject>Synthesis</subject><subject>transfer hydrogenation</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkD1PwzAQhiMEEp8rs0eWFNtJ7GYsoRREC1JbBJvl2OdiSJ1ip0D-PamKKjamO937PDe8UXROcI9gTC-lDqpHMckwTjjdi44II1mcEpbv7_YMH0bHIbxhTHif86MoDI2xyoJr0DCeQQWqsZ-A5l66YMCjGSzta6t9vQAnG1s7VBs0qN5bBwGVLZpAB25uY7uQTscTaGSFirpege94t0DTdfMKzq6XqJBd1obmNDowsgpw9jtPoqeb4by4jcePo7tiMI5VyhIa87zENCsZJjQjpeREZ0Yrk-M05TqlGlgCgHOZKNMHSbRUFLgpGdU5lUomyUl0sf278vXHGkIjljYoqCrpoF4HQTjp55SlpN-hvS2qfB2CByNW3i6lbwXBYtOu2LQrdu12Qr4VvmwF7T-0GFzPir9uvHVtaOB750r_LhhPeCaeH0aCv9yzq-n0WtwnP2tbj6Q</recordid><startdate>20150706</startdate><enddate>20150706</enddate><creator>Musa, Sanaa</creator><creator>Ghosh, Amrita</creator><creator>Vaccaro, Luigi</creator><creator>Ackermann, Lutz</creator><creator>Gelman, Dmitri</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20150706</creationdate><title>Efficient E-Selective Transfer Semihydrogenation of Alkynes by Means of Ligand-Metal Cooperating Ruthenium Catalyst</title><author>Musa, Sanaa ; Ghosh, Amrita ; Vaccaro, Luigi ; Ackermann, Lutz ; Gelman, Dmitri</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4632-79b025b601251ba71d5fdcf90447d42de63ee09a3cf8ea1dac2e7fb62d92aca33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alkenes</topic><topic>Alkynes</topic><topic>Catalysts</topic><topic>Formates</topic><topic>Formic acid</topic><topic>isotope labelling</topic><topic>ligand-metal cooperation</topic><topic>ruthenium</topic><topic>semihydrogenation of alkynes</topic><topic>Sodium</topic><topic>Styrenes</topic><topic>Synthesis</topic><topic>transfer hydrogenation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Musa, Sanaa</creatorcontrib><creatorcontrib>Ghosh, Amrita</creatorcontrib><creatorcontrib>Vaccaro, Luigi</creatorcontrib><creatorcontrib>Ackermann, Lutz</creatorcontrib><creatorcontrib>Gelman, Dmitri</creatorcontrib><collection>Istex</collection><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>Musa, Sanaa</au><au>Ghosh, Amrita</au><au>Vaccaro, Luigi</au><au>Ackermann, Lutz</au><au>Gelman, Dmitri</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient E-Selective Transfer Semihydrogenation of Alkynes by Means of Ligand-Metal Cooperating Ruthenium Catalyst</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2015-07-06</date><risdate>2015</risdate><volume>357</volume><issue>10</issue><spage>2351</spage><epage>2357</epage><pages>2351-2357</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>The manuscript describes an efficient protocol for the E‐selective transfer semihydrogenation of internal alkynes employing a previously described bifunctional ruthenium‐based PC(sp3)P complex, 20 mol% of sodium formate and nearly stoichiometric formic acid. Semihydrogenation of the terminal alkynes results in the formation of the corresponding styrenes. The mechanism of the reaction includes stepwise transfer of both the hydride and the proton of the formic acid to the substrate. This fact allowed for the development of a facile protocol for the synthesis of monodeuterated alkenes by simply applying formic acid/sodium formate/D2O mixture as a hydrogen source. 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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkenes Alkynes Catalysts Formates Formic acid isotope labelling ligand-metal cooperation ruthenium semihydrogenation of alkynes Sodium Styrenes Synthesis transfer hydrogenation |
| title | Efficient E-Selective Transfer Semihydrogenation of Alkynes by Means of Ligand-Metal Cooperating Ruthenium Catalyst |
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