Heat and shock sensitive tosyl azide was generated and used on demand in a telescoped diazo transfer process. Small quantities of tosyl azide were accessed in a 'one pot' batch procedure using shelf stable, readily available reagents. For large scale diazo transfer reactions tosyl azide was generated and used in a telescoped flow process, to mitigate the risks associated with handling potentially explosive reagents on scale. The in situ formed tosyl azide was used to rapidly perform diazo transfer to a range of acceptors, including β-ketoesters, β-ketoamides, malonate esters and β-ketosulfones. An effective in-line quench of sulfonyl azides was also developed, whereby a sacrificial acceptor molecule ensured complete consumption of any residual hazardous diazo transfer reagent. The telescoped diazo transfer process with in-line quenching was used to safely prepare over 21 g of an α-diazocarbonyl in >98% purity without any column chromatography.
CITATION STYLE
Deadman, B. J., O’Mahony, R. M., Lynch, D., Crowley, D. C., Collins, S. G., & Maguire, A. R. (2016). Taming tosyl azide: The development of a scalable continuous diazo transfer process. Organic and Biomolecular Chemistry, 14(13), 3423–3431. https://doi.org/10.1039/c6ob00246c
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