Synthesis of silylbut-1-en-3-ynes and buta-1,3-dienes as building blocks via hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne
Abstract The selective and efficient synthesis of (E)-1,2,4-trisilylbut-1-en-3-ynes obtained via Pt-catalyzed hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne is described. Optimized reaction conditions (Pt(PPh3)4) or Pt2(dvs)3, 100 °C, toluene, 18 h) yielded compounds with high isolation yi...
Saved in:
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Nature Portfolio
2024-12-01
|
| Series: | Scientific Reports |
| Subjects: | |
| Online Access: | https://doi.org/10.1038/s41598-024-82198-w |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1850131330251096064 |
|---|---|
| author | Kinga Stefanowska-Kątna Jędrzej Walkowiak Adrian Franczyk |
| author_facet | Kinga Stefanowska-Kątna Jędrzej Walkowiak Adrian Franczyk |
| author_sort | Kinga Stefanowska-Kątna |
| collection | DOAJ |
| description | Abstract The selective and efficient synthesis of (E)-1,2,4-trisilylbut-1-en-3-ynes obtained via Pt-catalyzed hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne is described. Optimized reaction conditions (Pt(PPh3)4) or Pt2(dvs)3, 100 °C, toluene, 18 h) yielded compounds with high isolation yields (76–95%). The modification of (E)-1,2,4-trisilylbut-1-en-3-ynes was further tested in protodesilylation, halodesilylation, hydrosilylation, and Pd-based cross-coupling reactions, resulting in a broad spectrum of new products. These compounds represent new families of buta-1,3-dienes, (E,E)-2,3-bissilylbuta-1,3-dienes, (E,E)-1,2,3-trisilylbuta-1,3-dienes, and (E,E)-1,2,3-trisilylbuta-1,3-dienes, which are ideally suited to silicon-based transformations and are perfect models for the investigation of the reactivity of one silyl group in the presence of another. |
| format | Article |
| id | doaj-art-abe589f1b3564ca3904eb38d522d104b |
| institution | OA Journals |
| issn | 2045-2322 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj-art-abe589f1b3564ca3904eb38d522d104b2025-08-20T02:32:26ZengNature PortfolioScientific Reports2045-23222024-12-011411710.1038/s41598-024-82198-wSynthesis of silylbut-1-en-3-ynes and buta-1,3-dienes as building blocks via hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyneKinga Stefanowska-Kątna0Jędrzej Walkowiak1Adrian Franczyk2Center for Advanced Technologies, Adam Mickiewicz UniversityCenter for Advanced Technologies, Adam Mickiewicz UniversityCenter for Advanced Technologies, Adam Mickiewicz UniversityAbstract The selective and efficient synthesis of (E)-1,2,4-trisilylbut-1-en-3-ynes obtained via Pt-catalyzed hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne is described. Optimized reaction conditions (Pt(PPh3)4) or Pt2(dvs)3, 100 °C, toluene, 18 h) yielded compounds with high isolation yields (76–95%). The modification of (E)-1,2,4-trisilylbut-1-en-3-ynes was further tested in protodesilylation, halodesilylation, hydrosilylation, and Pd-based cross-coupling reactions, resulting in a broad spectrum of new products. These compounds represent new families of buta-1,3-dienes, (E,E)-2,3-bissilylbuta-1,3-dienes, (E,E)-1,2,3-trisilylbuta-1,3-dienes, and (E,E)-1,2,3-trisilylbuta-1,3-dienes, which are ideally suited to silicon-based transformations and are perfect models for the investigation of the reactivity of one silyl group in the presence of another.https://doi.org/10.1038/s41598-024-82198-w1,4-Bis(trimethylsilyl)buta-1,3-diyneHydrosilylationBut-1-en-3-ynes1,3-dienesBuilding blocks |
| spellingShingle | Kinga Stefanowska-Kątna Jędrzej Walkowiak Adrian Franczyk Synthesis of silylbut-1-en-3-ynes and buta-1,3-dienes as building blocks via hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne Scientific Reports 1,4-Bis(trimethylsilyl)buta-1,3-diyne Hydrosilylation But-1-en-3-ynes 1,3-dienes Building blocks |
| title | Synthesis of silylbut-1-en-3-ynes and buta-1,3-dienes as building blocks via hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne |
| title_full | Synthesis of silylbut-1-en-3-ynes and buta-1,3-dienes as building blocks via hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne |
| title_fullStr | Synthesis of silylbut-1-en-3-ynes and buta-1,3-dienes as building blocks via hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne |
| title_full_unstemmed | Synthesis of silylbut-1-en-3-ynes and buta-1,3-dienes as building blocks via hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne |
| title_short | Synthesis of silylbut-1-en-3-ynes and buta-1,3-dienes as building blocks via hydrosilylation of 1,4-bis(trimethylsilyl)buta-1,3-diyne |
| title_sort | synthesis of silylbut 1 en 3 ynes and buta 1 3 dienes as building blocks via hydrosilylation of 1 4 bis trimethylsilyl buta 1 3 diyne |
| topic | 1,4-Bis(trimethylsilyl)buta-1,3-diyne Hydrosilylation But-1-en-3-ynes 1,3-dienes Building blocks |
| url | https://doi.org/10.1038/s41598-024-82198-w |
| work_keys_str_mv | AT kingastefanowskakatna synthesisofsilylbut1en3ynesandbuta13dienesasbuildingblocksviahydrosilylationof14bistrimethylsilylbuta13diyne AT jedrzejwalkowiak synthesisofsilylbut1en3ynesandbuta13dienesasbuildingblocksviahydrosilylationof14bistrimethylsilylbuta13diyne AT adrianfranczyk synthesisofsilylbut1en3ynesandbuta13dienesasbuildingblocksviahydrosilylationof14bistrimethylsilylbuta13diyne |