A Safe and Simple Synthesis of 1,4-Bis(trimethylsilyl)buta-1,3-diyne*
Sören Bock A and Paul J. Low A B
+ Author Affiliations
- Author Affiliations
A School of Chemistry and Biochemistry, University of Western Australia, 35 Stirling Highway, Crawley, WA 6009, Australia.
B Corresponding author. Email: paul.low@uwa.edu.au
Australian Journal of Chemistry 71(4) 307-310 https://doi.org/10.1071/CH17402
Submitted: 17 July 2017 Accepted: 22 August 2017 Published: 19 September 2017
Abstract
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.
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