3 years ago

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

General and Efficient Intermolecular [2+2] Photodimerization of Chalcones and Cinnamic Acid Derivatives in Solution through Visible-Light Catalysis
Mao-Yong Huang, Qing-Yuan Meng, Vaidhyanathan Ramamurthy, Lei-Min Zhao, Li-Zhu Wu, Tao Lei, Chen-Ho Tung, Hongyan Xiao, Bing Yang, Chen Ye, Chao Zhou
[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. Circle of light: Visible-light-induced energy transfer can be used to construct cyclobutanes from nonrigid olefins in a highly regio- and diastereoselective manner through [2+2] photocycloaddition. Chalcones and cinnamic acid derivatives were reacted to give cyclobutanes with high yields at room temperature.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708559

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