General and Efficient Intermolecular [2+2] Photodimerization of Chalcones and Cinnamic Acid Derivatives in Solution through Visible-Light Catalysis

Tao Lei, Chao Zhou, Mao Yong Huang, Lei Min Zhao, Bing Yang, Chen Ye, Hongyan Xiao, Qing Yuan Meng, Vaidhyanathan Ramamurthy, Chen Ho Tung, Li Zhu Wu

Research output: Contribution to journalArticle

41 Scopus citations

Abstract

[2+2] Photocycloaddition, for example, the dimerization of chalcones and cinnamic acid derivatives, is a unique strategy to construct cyclobutanes, which are building blocks for a variety of biologically active molecules and natural products. However, most attempts at the above [2+2] addition have focused on solid-state, molten-state, or host–guest systems under ultraviolet-light irradiation in order to overcome the competition of facile geometric isomerization of nonrigid olefins. We report a general and simple method to realize the intermolecular [2+2] dimerization reaction of these acyclic olefins to construct cyclobutanes in a highly regio- and diastereoselective manner in solution under visible light, which provides an efficient solution to a long-standing problem.

Original languageEnglish (US)
Pages (from-to)15407-15410
Number of pages4
JournalAngewandte Chemie - International Edition
Volume56
Issue number48
DOIs
StatePublished - Nov 27 2017

Keywords

  • [2+2] cycloaddition
  • chalcones
  • cinnamic acid
  • cyclobutanes
  • visible-light catalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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