An Aminative Rearrangement of O-(Arenesulfonyl)hydroxylamines: Facile Access to ortho-Sulfonyl Anilines.
Gillespie, James E
Angew Chem Int Ed Engl
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Morrill, C., Gillespie, J. E., & Phipps, R. (2022). An Aminative Rearrangement of O-(Arenesulfonyl)hydroxylamines: Facile Access to ortho-Sulfonyl Anilines.. Angew Chem Int Ed Engl https://doi.org/10.1002/anie.202204025
Ortho-sulfonyl anilines are important building blocks for a range of applications. We report the discovery of an aromatic rearrangement reaction of O-(arenesulfonyl)hydroxylamines which leads directly to ortho-sulfonyl anilines through formation of a new C-N bond with excellent levels of regiocontrol for the ortho position(s) over all others. We establish that the rearrangement is proceeding through an intermolecular mechanism and propose that the regiocontrol observed is the result of attractive non-covalent interactions occurring during the C-N bond forming step. Importantly, this method is complementary to classical aniline sulfonation in terms of the variously substituted regioisomers that can be obtained and it is also applicable to O-(benzylsulfonyl) hydroxylamines.
Royal Society (RGF/EA/180005)
European Research Council (757381)
Engineering and Physical Sciences Research Council (EP/S03269X/1)
Royal Society (URF\R\191003)
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External DOI: https://doi.org/10.1002/anie.202204025
This record's URL: https://www.repository.cam.ac.uk/handle/1810/338142
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