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

[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 f...

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Bibliographic Details
Published in:Angewandte Chemie 2017-11, Vol.129 (48), p.15609-15612
Main Authors: Lei, Tao, Zhou, Chao, Huang, Mao‐Yong, Zhao, Lei‐Min, Yang, Bing, Ye, Chen, Xiao, Hongyan, Meng, Qing‐Yuan, Ramamurthy, Vaidhyanathan, Tung, Chen‐Ho, Wu, Li‐Zhu
Format: Article
Language:English
Subjects:
[2+2]-Cycloadditionen
Alkenes
Biological activity
Catalysis
Chalcone
Chemistry
Cinnamic acid
Cyclobutane
Derivatives
Dimerization
Irradiation
Isomerization
Katalyse mit sichtbarem Licht
Light irradiation
Natural products
Supramolecular compounds
Ultraviolet radiation
Zinnsäure
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Summary:[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. Licht‐Kreise: Durch sichtbares Licht induzierter Energietransfer kann genutzt werden, um durch [2+2]‐Photocycloaddition Cyclobutane aus strukturflexiblen Olefinen in regio‐ und diastereoselektiver Weise aufzubauen. Chalcon‐ und Zinnsäure‐Derivate wurden bei Raumtemperatur in hohen Ausbeuten zu Cyclobutanen umgesetzt.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201708559