4.5 Article

Visible-Light-Facilitated 5-exo-trig Cyclization of 1,6-Dienes with Alkyl Chlorides: Selective Scission of the C(sp3)-H Bond in Alkyl Chlorides

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 6, Pages 1177-1181

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301849

Keywords

Radicals; Cyclization; Dienes; C-H activation; Nitrogen heterocycles

Funding

  1. National Natural Science Foundation of China [21172060]
  2. Specialized Research Fund for Doctoral Program of Higher Education [20120161110041]
  3. Hunan Provincial Natural Science Foundation of China [13JJ2018]

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A general and conceptually novel method for preparing polychloro-substituted pyrrolidin-2-ones and indeno[2,1-c]pyrrol-3(3aH)-ones is established by visible-light-facilitated 5-exo-trig cyclization of 1,6-dienes with alkyl chlorides through selectively splitting the C(sp(3))-H bond adjacent to the chloride atom to form an alkyl radical.

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