Ketone-catalyzed photochemical C(sp3)–H chlorination

Lei Han, Ji Bao Xia, Lin You, Chuo Chen

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

Photoexcited arylketones catalyze the direct chlorination of C(sp3)–H groups by N- chlorosuccinimide. Acetophenone is the most effective catalyst for functionalization of unactivated C–H groups while benzophenone provides better yields for benzylic C–H functionalization. Activation of both acetophenone and benzophenone can be achieved by irradiation with a household compact fluorescent lamp. This light-dependent reaction provides a better control of the reaction as compared to the traditional chlorination methods that proceed through a free radical chain propagation mechanism.

Original languageEnglish (US)
Pages (from-to)3696-3701
Number of pages6
JournalTetrahedron
Volume73
Issue number26
DOIs
StatePublished - 2017

Keywords

  • Arylketone
  • Chlorination
  • C–H functionalization
  • Photochemistry
  • Visible light

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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