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

McCaw, Patrick G.; Deadman, Benjamin J.; Maguire, Anita R.; Collins, Stuart G.

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

dc.contributor.author	McCaw, Patrick G.
dc.contributor.author	Deadman, Benjamin J.
dc.contributor.author	Maguire, Anita R.
dc.contributor.author	Collins, Stuart G.
dc.contributor.funder	Irish Research Council for Science Engineering and Technology	en
dc.contributor.funder	Science Foundation Ireland	en
dc.date.accessioned	2016-07-19T10:24:03Z
dc.date.available	2016-07-19T10:24:03Z
dc.date.issued	2016-07-04
dc.description.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.	en
dc.description.sponsorship	Science Foundation Ireland (Grant Number: SFI SSPC2 12/RC/2275)	en
dc.description.status	Peer reviewed	en
dc.description.version	Accepted Version	en
dc.format.mimetype	application/pdf	en
dc.identifier.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	en
dc.identifier.doi	10.1556/1846.2016.00013
dc.identifier.endpage	233	en
dc.identifier.issn	2062-249X
dc.identifier.issn	2063-0212
dc.identifier.issued	3
dc.identifier.journaltitle	Journal of Flow Chemistry	en
dc.identifier.startpage	226	en
dc.identifier.uri	https://hdl.handle.net/10468/2899
dc.identifier.volume	6
dc.language.iso	en	en
dc.publisher	Akadémiai Kiadó, Budapest	en
dc.rights	© 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	en
dc.subject	Diazo transfer	en
dc.subject	Sulfoxides	en
dc.subject	Continuous flow	en
dc.subject	Immobilised base	en
dc.subject	Solid-phase synthesis	en
dc.subject	Residence time control	en
dc.title	Delivering enhanced efficiency in the synthesis of α-diazosulfoxides by exploiting the process control enabled in flow	en
dc.type	Article (peer-reviewed)	en