4.7 Article

Visible-Light-Mediated Annulation of Electron-Rich Alkenes and Nitrogen-Centered Radicals from N-Sulfonylallylamines: Construction of Chloromethylated Pyrrolidine Derivatives

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 24, 页码 13093-13108

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02146

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资金

  1. Pfizer
  2. EPSRC Grants [EP/K009494/1, EP/M004120/1]
  3. EPSRC [EP/K009494/1, EP/M004120/1] Funding Source: UKRI
  4. Engineering and Physical Sciences Research Council [EP/M004120/1, EP/K009494/1] Funding Source: researchfish

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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 photocatalyst 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.

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