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

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...

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Published inJournal of organic chemistry Vol. 83; no. 23; pp. 14419 - 14430
Main Authors Sun, Kai, Chen, Xiao-Lan, Li, Shi-Jun, Wei, Dong-Hui, Liu, Xiao-Ceng, Zhang, Yin-Li, Liu, Yan, Fan, Lu-Lu, Qu, Ling-Bo, Yu, Bing, Li, Kai, Sun, Yuan-Qiang, Zhao, Yu-Fen
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.12.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AGGREGATION-INDUCED EMISSION
ONE-POT SYNTHESIS
MEDIATED SULFONYLATION
UNSYMMETRICAL NONSTEROIDAL LIGANDS
PHOTOCHEMICAL TRANSFORMATION
EFFICIENT SYNTHESIS
MEOTF-INDUCED CARBOANNULATION
TANDEM CYCLIZATION
BINDING ORIENTATION
C-H
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Summary: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.
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02175