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Copper-Catalyzed Radical Cascade Cyclization To Access 3‑Sulfonated Indenones with the AIE Phenomenon

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posted on 01.11.2018, 00:00 by Kai Sun, Xiao-Lan Chen, Shi-Jun Li, Dong-Hui Wei, Xiao-Ceng Liu, Yin-Li Zhang, Yan Liu, Lu-Lu Fan, Ling-Bo Qu, Bing Yu, Kai Li, Yuan-Qiang Sun, Yu-Fen Zhao
An efficient copper-catalyzed radical cascade cyclization strategy was developed, by which a wide variety of 3-sulfonyl substituted indenones were prepared in one pot via reaction of 2-alkynylbenzonitriles with sulfonyl hydrazides in the presence of TBHP and CuI under mild reaction conditions. Much more importantly, the 3-sulfonyl indenones, synthesized through our newly developed copper-catalyzed radical cascade cyclization strategy, were found to own typical aggregation-induced emission (AIE) properties, showing orange to red emission with large Stokes shift (more than 135 nm). In addition, such newly found AIEgens could be successfully used in live cell imaging, exhibiting excellent biocompatibility and application potential.