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A Safe and Simple Synthesis of 1,4-Bis(trimethylsilyl)buta-1,3-diyne*
Australian Journal of Chemistry ( IF 1.0 ) Pub Date : 2017-09-19 , DOI: 10.1071/ch17402
Sören Bock , Paul J. Low

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.



中文翻译:

安全,简单地合成1,4-双(三甲基甲硅烷基)buta-1,3-diyne *

buta-1,3-diyne synthon 1,4-bis(trimethylsilyl)buta-1,3-diyne(1)是将butadiyne图案引入有机和有机金属结构的重要组成部分。尽管1通常从干草HOMO耦合三甲基硅烷基的(催化的CuI / tetramethylethynylenediamine,O-制备2,丙酮),一个显著爆炸的这个制备过程中的报告,有可能从一个静电放电加入催化剂溶液中,以炔过程中产生的/丙酮/ O 2气氛浓郁,促使人们考虑使用其他程序。在这里,我们报告了耐用的Navale催化剂体系(CuI / NN-二甲基氨基吡啶,O 2,NCMe)中的多克规模制备1与全玻璃装置的最小的操作,大大地简化了工艺并最小化与该有用的化合物的制备方法相关的风险。

更新日期:2017-09-19
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