Construction of Cyclobutanes by Multicomponent Cascade Reactions in Homogeneous Solution through Visible-Light Catalysis

被引:14
作者
Lei, Tao [1 ,2 ]
Zhou, Chao [1 ,2 ]
Wei, Xiang-Zhu [1 ,2 ]
Yang, Bing [1 ,2 ]
Chen, Bin [1 ,2 ]
Tung, Chen-Ho [1 ,2 ]
Wu, Li-Zhu [1 ,2 ]
机构
[1] Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Sch Future Technol, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
aldol reaction; cyclobutane; multicomponent cascade reactions; 2+2] photocycloaddition; Witting reactions; 2+2 PHOTOCYCLOADDITION REACTIONS; TEMPLATING PHOTODIMERIZATION; PHOTOCHEMICAL-REACTIONS; PHOTOREDOX CATALYSIS; TRIPLET-STATE; SOLID-STATE; PHOTOCATALYSIS; CYCLOADDITION; ISOMERIZATION; EXPLORATION;
D O I
10.1002/chem.201804946
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
[2+2] Photocycloaddition of two olefins is a general method to assemble the core scaffold, cyclobutane, found in numerous bioactive molecules. A new approach to synthesize cyclobutanes through multicomponent cascade reactions by merging aldol reaction and Witting reaction with visible-light-induced [2+2] cycloaddition is reported. An array of cyclobutanes with high selectivity has been achieved from commercially available aldehydes, ketones (or phosphorus ylide), and olefins with visible-light irradiation of a catalytic amount of (fac-tris(2-phenylpyridinato-C-2,N)iridium) ([Ir(ppy)(3)]) at room temperature. Control experiments and spectroscopic studies revealed that the triplet-triplet energy transfer from the excited [Ir(ppy)(3)]* to enones, generated in situ from aldehyde and ketone or aldehyde and phosphorus ylide, is responsible for these simple and efficient muticomponent transformations.
引用
收藏
页码:879 / 884
页数:6
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