A general electron donor–acceptor complex for photoactivation of arenes via thianthrenation |
| |
Authors: | Kai Sun Anzai Shi Yan Liu Xiaolan Chen Panjie Xiang Xiaotong Wang Lingbo Qu Bing Yu |
| |
Institution: | Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001 China.; Henan International Joint Laboratory of Rare Earth Composite Material, College of Materials Engineering, Henan University of Engineering, Zhengzhou 451191 China |
| |
Abstract: | General photoactivation of electron donor–acceptor (EDA) complexes between arylsulfonium salts and 1,4-diazabicyclo2.2.2]octane with visible light or natural sunlight was discovered. This practical and efficient mode enables the production of aryl radicals under mild conditions, providing an unrealized opportunity for two-step para-selective C–H functionalization of complex arenes. The novel mode for generating aryl radicals via an EDA complex was well supported by UV-vis absorbance measurements, nuclear magnetic resonance titration experiments, and density functional theory (DFT) calculations. The method was applied to the regio- and stereo-selective arylation of various N-heterocycles under mild conditions, yielding an assembly of challengingly linked heteroaryl–(hetero)aryl products. Remarkably, the meaningful couplings of bioactive molecules with structurally complex drugs or agricultural pharmaceuticals were achieved to display favorable in vitro antitumor activities, which will be of great value in academia or industry.General photoactivation of EDA complexes between arylsulfonium salts and 1,4-diazabicyclo2.2.2]octane was discovered. This practical mode enables the generation of aryl radicals for C–H functionalization of arenes. |
| |
Keywords: | |
|
|