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General and Efficient Intermolecular [2+2] Photodimerization of Chalcones and Cinnamic Acid Derivatives in Solution through Visible‐Light Catalysis
Author(s) -
Lei Tao,
Zhou Chao,
Huang MaoYong,
Zhao LeiMin,
Yang Bing,
Ye Chen,
Xiao Hongyan,
Meng QingYuan,
Ramamurthy Vaidhyanathan,
Tung ChenHo,
Wu LiZhu
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201708559
Subject(s) - cyclobutanes , cinnamic acid , isomerization , intermolecular force , chemistry , photochemistry , catalysis , molecule , visible spectrum , combinatorial chemistry , organic chemistry , cycloaddition , materials science , optoelectronics
[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.