Au(I)/Sc(III)-co-catalyzed tandem spiroannulation/cycloisomerization of 3-(2-ethynylaryl)- N -tosylaziridines with indoles to access 5 H -benzo[ b ]carbazoles

An unusual spiroannulation/cycloisomerization cascade of 3-(2-ethynylaryl)- -tosylaziridines with indoles enabled by cooperative gold/scandium catalysis is presented, which facilitates the synthesis of 5 -benzo[ ]carbazoles in moderate to excellent yields. This protocol features a broad substrate sc...

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Veröffentlicht in:Organic & biomolecular chemistry 2024-07, Vol.22 (29), p.5999-6003
Hauptverfasser: Wang, Wei, Zheng, Lan, Liang, Wen-Jie, Fu, Xin-Yi, Zhang, Yu-Qing, Meng, Ru-Fang, Zhang, Huan, Lin, Chenxiang, Su, Wei, Xiao, Jun-An
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Sprache:eng
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Zusammenfassung:An unusual spiroannulation/cycloisomerization cascade of 3-(2-ethynylaryl)- -tosylaziridines with indoles enabled by cooperative gold/scandium catalysis is presented, which facilitates the synthesis of 5 -benzo[ ]carbazoles in moderate to excellent yields. This protocol features a broad substrate scope and good functional-group compatibility. Additionally, the resulting 5 -benzo[ ]carbazoles exhibit good fluorescence properties, demonstrating the synthetic practicality of this method. Moreover, control experiments were performed to illustrate the reaction mechanism.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00782d