A Safe and Simple Synthesis of 1,4-Bis(trimethylsilyl)buta-1,3-diyne
| Autor: | Paul J. Low, Sören Bock |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Green chemistry Trimethylsilyl 010405 organic chemistry Synthon Alkyne General Chemistry 010402 general chemistry 01 natural sciences Trimethylsilylacetylene 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Biocatalysis Acetone Organic chemistry |
| Zdroj: | Australian Journal of Chemistry. 71:307 |
| ISSN: | 0004-9425 |
| Popis: | The buta-1,3-diyne synthon 1,4-bis(trimethylsilyl)buta-1,3-diyne (1) is an important building block for the introduction of butadiyne motifs into organic and organometallic structures. Although 1 is commonly prepared from the Hay homo-coupling of trimethylsilylacetylene (catalytic CuI/tetramethylethynylenediamine, O2, acetone), the report of a significant explosion during this preparation, likely arising from a static discharge during addition of the catalyst solution to the alkyne/acetone/O2 rich atmosphere, prompts consideration of alternative procedures. Here we report the use of the robust Navale catalyst system (CuI/N,N-dimethylaminopyridine, O2, NCMe) in the multigram-scale preparation of 1 with minimal manipulation of all-glass apparatus, greatly simplifying the process and minimising risks associated with the preparation of this useful compound. |
| Databáze: | OpenAIRE |
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