Visible Light/Copper Catalysis-Enabled Arylation and Alkenylation of Phosphorothioates via Site-Selective C–H Thianthrenation
Guoju Guo, Jie Ma, Yuzhen Dong, Qilong Wu, Jian Lv, Yongjia Shi, Daoshan Yang
Abstract
An efficient visible light/copper-enabled arylation and alkenylation of phosphorothioates with thianthrenium salts via a C(sp 2 )–S cross-coupling reaction have been demonstrated. This strategy uses aryl/alkenyl thianthrenium salts as new electrophilic reagents, which can be easily prepared by the site-selective C–H thianthrenation of arenes/alkenes with high regioselectivity. Mechanistic studies revealed a crucial role of the in situ formed copper–sulfur complex, which undergoes a facile SET process with the thianthrenium salts under visible light conditions, thereby successfully achieving the desired cross-coupling reactivity.
Topics & Concepts
ChemistryCatalysisCopperCombinatorial chemistryPhotochemistryVisible spectrumStereochemistryOrganic chemistryOptoelectronicsPhysicsSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods