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

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

doi:10.1556/1846.2016.00013

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Journal of Flow Chemistry

Volume/Issue:: Volume 6: Issue 3

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

Authors:

Patrick G. McCaw

Patrick G. McCaw University College Cork, Cork, Ireland

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Benjamin J. Deadman

Benjamin J. Deadman University College Cork, Cork, Ireland

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Anita R. Maguire

Anita R. Maguire University College Cork, Cork, Ireland
University College Cork, Cork, Ireland

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a.maguire@ucc.ie

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Stuart G. Collins

Stuart G. Collins University College Cork, Cork, Ireland

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stuart.collins@ucc.ie

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Pages:: 226–233

Online Publication Date:: Sep 2016

Publication Date:: 01 Sep 2016

Article Category:: Research Article

DOI:: https://doi.org/10.1556/1846.2016.00013

Keywords:: diazo transfer; sulfoxides; continuous flow; immobilized base; solid-phase synthesis; residence time control

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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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Journal of Flow Chemistry A Journal of the Flow Chemistry Society

Print ISSN:: 2062-249X

Online ISSN:: 2063-0212

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Journal of Flow Chemistry
Language	English
Size	A4
Year of Foundation	2011
Volumes per Year	1
Issues per Year	4
Founder	Áramlásos Kémiai Tudományos Társaság
Founder's Address	H-1031 Budapest, Hungary Záhony utca 7.
Publisher	Akadémiai Kiadó Springer Nature Switzerland AG
Publisher's Address	H-1117 Budapest, Hungary 1516 Budapest, PO Box 245. CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible Publisher	Chief Executive Officer, Akadémiai Kiadó
ISSN	2062-249X (Print)
ISSN	2063-0212 (Online)