Delivering enhanced efficiency in the synthesis of α-diazosulfoxides by exploiting the process control enabled in flow

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PMC Manuscript for CORA.pdf(1.05 MB)
Accepted Version
Date
2016-07-04
Authors
McCaw, Patrick G.
Deadman, Benjamin J.
Maguire, Anita R.
Collins, Stuart G.
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Akadémiai Kiadó, Budapest
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Abstract
Continuous-flow generation of α-diazosulfoxides results in a two- to three-fold increase in yields and decreased reaction times compared to standard batch synthesis methods. These high yielding reactions are enabled by flowing through a bed of polystyrene-supported base (PS-DBU or PS-NMe2) with highly controlled residence times. This engineered solution allows the α-diazosulfoxides to be rapidly synthesized while limiting exposure of the products to basic reaction conditions, which have been found to cause rapid decomposition. In addition to improved yields, this work has the added advantage of ease of processing, increased safety profile, and scale-up potential.
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Keywords
Diazo transfer , Sulfoxides , Continuous flow , Immobilised base , Solid-phase synthesis , Residence time control
Citation
McCaw, P.G., Deadman, B.J., Maguire, A.R. and Collins, S.G. (2016) ‘Delivering enhanced efficiency in the synthesis of α-diazosulfoxides by exploiting the process control enabled in flow’, Journal of Flow Chemistry, 6(3), pp. 226-233. doi:10.1556/1846.2016.00013
Copyright
© 2016, Akadémiai Kiadó Zrt. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Flow Chemistry. To access the final edited and published work see http://dx.doi.org/10.1556/1846.2016.00013