Visible-Light-Mediated Annulation of Electron-Rich Alkenes and Nitrogen-Centered Radicals from N-Sulfonylallylamines: Construction of Chloromethylated Pyrrolidine Derivatives.
Journal of Organic Chemistry
American Chemical Society (ACS)
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Crespin, L., Greb, A., Blakemore, D. C., & Ley, S. (2017). Visible-Light-Mediated Annulation of Electron-Rich Alkenes and Nitrogen-Centered Radicals from N-Sulfonylallylamines: Construction of Chloromethylated Pyrrolidine Derivatives.. Journal of Organic Chemistry, 82 (24), 13093-13108. https://doi.org/10.1021/acs.joc.7b02146
A visible-light-mediated annulation of N-sulfonylallylamines and olefins is reported. Rapid access to highly functionalized chloromethylated pyrrolidines can be achieved using mild conditions for the generation of nitrogen-centered radicals. Both a transition-metal-based catalyst and an organic dye can be used as photosensitizers with 0.5 mol % loading. The reaction was found to be applicable to a large variety of electron-rich and electron-neutral olefins.
This work was supported by a postdoctoral fellowship from Pfizer (L.C. and A.G.) and the EPSRC Grants EP/K009494/1 and EP/M004120/1 (S.V.L.).
Engineering and Physical Sciences Research Council (EP/M004120/1)
Engineering and Physical Sciences Research Council (EP/K009494/1)
External DOI: https://doi.org/10.1021/acs.joc.7b02146
This record's URL: https://www.repository.cam.ac.uk/handle/1810/285414