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Issue 13, 2016
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Taming tosyl azide: the development of a scalable continuous diazo transfer process

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Abstract

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.

Graphical abstract: Taming tosyl azide: the development of a scalable continuous diazo transfer process

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Supplementary files

Article information


Submitted
28 Jan 2016
Accepted
26 Feb 2016
First published
01 Mar 2016

Org. Biomol. Chem., 2016,14, 3423-3431
Article type
Paper

Taming tosyl azide: the development of a scalable continuous diazo transfer process

B. J. Deadman, R. M. O'Mahony, D. Lynch, D. C. Crowley, S. G. Collins and A. R. Maguire, Org. Biomol. Chem., 2016, 14, 3423
DOI: 10.1039/C6OB00246C

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