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Synlett 2011(6): 869-873  
DOI: 10.1055/s-0030-1259923
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Oxidation Reactions in Segmented and Continuous Flow Chemical Processing Using an N-(tert-Butyl)phenylsulfinimidoyl Chloride Monolith

Heiko Lange, Matthew J. Capener, Alexander X. Jones, Catherine J. Smith, Nikzad Nikbin, Ian R. Baxendale, Steven V. Ley*
Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK
Fax: +44(1223)336442; e-Mail: svl1000@cam.ac.uk;
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Publikationsverlauf

Received 1 February 2011
Publikationsdatum:
16. März 2011 (online)

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Abstract

A supported version of N-(tert-butyl)phenylsulfinim­idoyl chloride on a monolithic material is described, which can be incorporated into a flow chemical processing arrangement to oxidise a variety of substrates in both stoichiometric and catalytic processes to yield products in high yields and in high purity after in-line workup.

Key words

oxidation - monolith - flow chemistry - polymer-­supported reagents - catalysis

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16

In cases where the correlation is not strictly linear, the monolith is likely to be of poor quality and should be discarded (see Supporting Information for details).

17

The Vapourtec R2+ and R4 units are available from Vapourtec Ltd, Park Farm Business Centre, Fornham St Genevieve, Bury St Edmunds, Suffolk, IP28 6TS, UK. Website: www.vapourtec.co.uk. See: Baumann, M.; Baxendale, I. R.; Ley, S.V.; Smith, S. D.; Tranmer, G. K. Org. Lett. 2006, 8, 5231.

18

The FlowSyn unit is available from Uniqsis Ltd., 29 Station Road, Shepreth, Cambridgeshire, SG8 6GB, UK. Website: www.uniqsis.com. See the following publication for the use of this platform as a scale-up facility: Palmieri, A.; Ley, S. V.; Hammond, K.; Polyzos, A.; Baxendale, I. R. Tetrahedron Lett. 2009, 50, 3287.