Rhenium-catalyzed reaction of α-alkyl substituted β-dicarbonyl compounds with organosilicon compounds
[Display omitted] •Re-catalyzed allylation and reduction of α-alkyl substituted β-dicarbonyl compounds.•The reactions proceeded through the elimination of the 1,3-dicarbonyl unit.•The allylation regioselectively proceeded with 3-trimethylsilyl-1-phenyl-2-propene. When α-alkyl substituted β-dicarbony...
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| Veröffentlicht in: | Tetrahedron letters 2025-01, Vol.154, p.155390, Article 155390 |
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| creator | Matsuda, Yuya Mori, Shintaro Tsuda, Susumu Nishiyama, Yutaka |
| description | [Display omitted]
•Re-catalyzed allylation and reduction of α-alkyl substituted β-dicarbonyl compounds.•The reactions proceeded through the elimination of the 1,3-dicarbonyl unit.•The allylation regioselectively proceeded with 3-trimethylsilyl-1-phenyl-2-propene.
When α-alkyl substituted β-dicarbonyl compounds were reacted with allylsilanes in the presence of a rhenium catalyst, the allylation of the benzylic carbon center proceeded through the elimination of the β-dicarbonyl unit to form the corresponding alkenes in moderate to good yields. Regarding the reaction with hydrosilane, the reduction of these compounds also proceeded through the elimination of the β-dicarbonyl unit to give the corresponding alkanes. |
| doi_str_mv | 10.1016/j.tetlet.2024.155390 |
| format | Article |
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•Re-catalyzed allylation and reduction of α-alkyl substituted β-dicarbonyl compounds.•The reactions proceeded through the elimination of the 1,3-dicarbonyl unit.•The allylation regioselectively proceeded with 3-trimethylsilyl-1-phenyl-2-propene.
When α-alkyl substituted β-dicarbonyl compounds were reacted with allylsilanes in the presence of a rhenium catalyst, the allylation of the benzylic carbon center proceeded through the elimination of the β-dicarbonyl unit to form the corresponding alkenes in moderate to good yields. Regarding the reaction with hydrosilane, the reduction of these compounds also proceeded through the elimination of the β-dicarbonyl unit to give the corresponding alkanes.</description><identifier>ISSN: 0040-4039</identifier><identifier>DOI: 10.1016/j.tetlet.2024.155390</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>alkenes ; Allylation ; carbon ; catalysts ; Reduction ; Renium ; rhenium</subject><ispartof>Tetrahedron letters, 2025-01, Vol.154, p.155390, Article 155390</ispartof><rights>2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c1337-a81a64adc59a9044c253ac9d18b3696587d463e9c49bc147a8618d069a3ce333</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040403924004854$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids></links><search><creatorcontrib>Matsuda, Yuya</creatorcontrib><creatorcontrib>Mori, Shintaro</creatorcontrib><creatorcontrib>Tsuda, Susumu</creatorcontrib><creatorcontrib>Nishiyama, Yutaka</creatorcontrib><title>Rhenium-catalyzed reaction of α-alkyl substituted β-dicarbonyl compounds with organosilicon compounds</title><title>Tetrahedron letters</title><description>[Display omitted]
•Re-catalyzed allylation and reduction of α-alkyl substituted β-dicarbonyl compounds.•The reactions proceeded through the elimination of the 1,3-dicarbonyl unit.•The allylation regioselectively proceeded with 3-trimethylsilyl-1-phenyl-2-propene.
When α-alkyl substituted β-dicarbonyl compounds were reacted with allylsilanes in the presence of a rhenium catalyst, the allylation of the benzylic carbon center proceeded through the elimination of the β-dicarbonyl unit to form the corresponding alkenes in moderate to good yields. Regarding the reaction with hydrosilane, the reduction of these compounds also proceeded through the elimination of the β-dicarbonyl unit to give the corresponding alkanes.</description><subject>alkenes</subject><subject>Allylation</subject><subject>carbon</subject><subject>catalysts</subject><subject>Reduction</subject><subject>Renium</subject><subject>rhenium</subject><issn>0040-4039</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2025</creationdate><recordtype>article</recordtype><recordid>eNp9kLtOwzAUhjOARLm8AUNGlhQ7dpx4QUIVN6kSEupuOcenrUsSF9sBlbeCB-kzkSqIkbP8w3-Rzpckl5RMKaHiejONGBuM05zkfEqLgklylEwI4STjhMmT5DSEDRlOVGSSrF7W2Nm-zUBH3ew-0aQeNUTrutQt0_1XppvXXZOGvg7Rxj4Ogf13ZixoX7tucMC1W9d3JqQfNq5T51e6c8E2FoaJP_M8OV7qJuDFr54li_u7xewxmz8_PM1u5xlQxspMV1QLrg0UUkvCOeQF0yANrWompCiq0nDBUAKXNVBe6krQyhAhNQNkjJ0lV-Ps1ru3HkNUrQ2ATaM7dH1QjBY8LwQtyyHKxyh4F4LHpdp622q_U5SoA0q1USNKdUCpRpRD7Was4fDFu0WvAljsAI31CFEZZ_8f-AFdhYQ4</recordid><startdate>20250101</startdate><enddate>20250101</enddate><creator>Matsuda, Yuya</creator><creator>Mori, Shintaro</creator><creator>Tsuda, Susumu</creator><creator>Nishiyama, Yutaka</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7S9</scope><scope>L.6</scope></search><sort><creationdate>20250101</creationdate><title>Rhenium-catalyzed reaction of α-alkyl substituted β-dicarbonyl compounds with organosilicon compounds</title><author>Matsuda, Yuya ; Mori, Shintaro ; Tsuda, Susumu ; Nishiyama, Yutaka</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1337-a81a64adc59a9044c253ac9d18b3696587d463e9c49bc147a8618d069a3ce333</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2025</creationdate><topic>alkenes</topic><topic>Allylation</topic><topic>carbon</topic><topic>catalysts</topic><topic>Reduction</topic><topic>Renium</topic><topic>rhenium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Matsuda, Yuya</creatorcontrib><creatorcontrib>Mori, Shintaro</creatorcontrib><creatorcontrib>Tsuda, Susumu</creatorcontrib><creatorcontrib>Nishiyama, Yutaka</creatorcontrib><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Matsuda, Yuya</au><au>Mori, Shintaro</au><au>Tsuda, Susumu</au><au>Nishiyama, Yutaka</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rhenium-catalyzed reaction of α-alkyl substituted β-dicarbonyl compounds with organosilicon compounds</atitle><jtitle>Tetrahedron letters</jtitle><date>2025-01-01</date><risdate>2025</risdate><volume>154</volume><spage>155390</spage><pages>155390-</pages><artnum>155390</artnum><issn>0040-4039</issn><abstract>[Display omitted]
•Re-catalyzed allylation and reduction of α-alkyl substituted β-dicarbonyl compounds.•The reactions proceeded through the elimination of the 1,3-dicarbonyl unit.•The allylation regioselectively proceeded with 3-trimethylsilyl-1-phenyl-2-propene.
When α-alkyl substituted β-dicarbonyl compounds were reacted with allylsilanes in the presence of a rhenium catalyst, the allylation of the benzylic carbon center proceeded through the elimination of the β-dicarbonyl unit to form the corresponding alkenes in moderate to good yields. Regarding the reaction with hydrosilane, the reduction of these compounds also proceeded through the elimination of the β-dicarbonyl unit to give the corresponding alkanes.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2024.155390</doi></addata></record> |
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| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | alkenes Allylation carbon catalysts Reduction Renium rhenium |
| title | Rhenium-catalyzed reaction of α-alkyl substituted β-dicarbonyl compounds with organosilicon compounds |
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