4.8 Article

Photoredox Imino Functionalizations of Olefins

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 43, Pages 13361-13365

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201708497

Keywords

cyclization; nitrogen heterocycles; photochemistry; radicals; reaction mechanisms

Funding

  1. European Union [PCIG13-GA-2013-631556]
  2. EPSRC [EP/P004997/1]
  3. Department of Chemistry, King Faisal University, Saudi Arabia
  4. Engineering and Physical Sciences Research Council [EP/P004997/1] Funding Source: researchfish
  5. EPSRC [EP/P004997/1] Funding Source: UKRI

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Shown herein is that polyfunctionalized nitrogen heterocycles can be easily prepared by a visible-light-mediated radical cascade process. This divergent strategy features the oxidative generation of iminyl radicals and subsequent cyclization/radical trapping, which allows the effective construction of highly functionalized heterocycles. The reactions proceed efficiently at room temperature, utilize an organic photocatalyst, use simple and readily available materials, and generate, in a single step, valuable building blocks that would be difficult to prepare by other methods.

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