Nitro-sulfinate Reductive Coupling to Access (Hetero)aryl Sulfonamides.
Accepted version
Peer-reviewed
Repository URI
Repository DOI
Change log
Authors
Abstract
A method to assemble (hetero)aryl sulfonamides via the reductive coupling of aryl sulfinates and nitroarenes is reported. Various reducing conditions with sodium bisulfite and with or without tin(II) chloride in DMSO were developed using an ultrasound bath to improve reaction homogeneity and mixing. A range of (hetero)aryl sulfonamides bearing a selection of functional groups were prepared, and the mechanism of the transformation was investigated. These investigations have led us to propose the formation of nitrosoarene intermediates, which were established via an independent molecular coupling strategy.
Description
Journal Title
J Org Chem
Conference Name
Journal ISSN
0022-3263
1520-6904
1520-6904
Volume Title
Publisher
American Chemical Society (ACS)
Publisher DOI
Rights and licensing
Except where otherwised noted, this item's license is described as Attribution 4.0 International
Sponsorship
Engineering and Physical Sciences Research Council (2276992)
SEG and HAE thank Pfizer Inc. for funding the postdoctoral fellowship. OMG acknowledges support from the EPSRC (EP/ S024220/1) SynTech Automated Centre for Chemical Synthe-sis, Centre for Doctoral Training in Cambridge, UK. SVL thanks the American Chemical Society for support through receipt of the Arthur C. Cope Award