Rhenium-Catalyzed anti-Markovnikov Addition Reaction of Methanetricarboxylates to Unactivated Terminal Acetylenes
A novel anti-Markovnikov addition reaction of methanetricarboxylates with terminal acetylenes under neutral conditions was achieved using a rhenium complex. This transformation represents a rare example of intermolecular anti-Markovnikov addition of carbon nucleophiles to unactivated terminal acetyl...
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| Veröffentlicht in: | Journal of the American Chemical Society 2015-02, Vol.137 (4), p.1452-1457 |
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| container_issue | 4 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 137 |
| creator | Hori, Shunsuke Murai, Masahito Takai, Kazuhiko |
| description | A novel anti-Markovnikov addition reaction of methanetricarboxylates with terminal acetylenes under neutral conditions was achieved using a rhenium complex. This transformation represents a rare example of intermolecular anti-Markovnikov addition of carbon nucleophiles to unactivated terminal acetylenes. 1,3-Diesters having bulky substituents at the active methylene carbon are also applicable as substrates to provide anti-Markovnikov adducts as single regio- and stereoisomers. Preliminary mechanistic studies imply that the rhenium vinylidene species is the key intermediate in the current catalytic cycle. |
| doi_str_mv | 10.1021/ja5090755 |
| format | Article |
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Am. Chem. Soc</addtitle><date>2015-02-04</date><risdate>2015</risdate><volume>137</volume><issue>4</issue><spage>1452</spage><epage>1457</epage><pages>1452-1457</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>A novel anti-Markovnikov addition reaction of methanetricarboxylates with terminal acetylenes under neutral conditions was achieved using a rhenium complex. This transformation represents a rare example of intermolecular anti-Markovnikov addition of carbon nucleophiles to unactivated terminal acetylenes. 1,3-Diesters having bulky substituents at the active methylene carbon are also applicable as substrates to provide anti-Markovnikov adducts as single regio- and stereoisomers. Preliminary mechanistic studies imply that the rhenium vinylidene species is the key intermediate in the current catalytic cycle.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25563809</pmid><doi>10.1021/ja5090755</doi><tpages>6</tpages></addata></record> |
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| source | American Chemical Society Journals |
| title | Rhenium-Catalyzed anti-Markovnikov Addition Reaction of Methanetricarboxylates to Unactivated Terminal Acetylenes |
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