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

Authors :
Wang W
Zheng L
Liang WJ
Fu XY
Zhang YQ
Meng RF
Zhang H
Lin C
Su W
Xiao JA
Source :
Organic & biomolecular chemistry [Org Biomol Chem] 2024 Jul 24; Vol. 22 (29), pp. 5999-6003. Date of Electronic Publication: 2024 Jul 24.
Publication Year :
2024

Abstract

An unusual spiroannulation/cycloisomerization cascade of 3-(2-ethynylaryl)- N -tosylaziridines with indoles enabled by cooperative gold/scandium catalysis is presented, which facilitates the synthesis of 5 H -benzo[ b ]carbazoles in moderate to excellent yields. This protocol features a broad substrate scope and good functional-group compatibility. Additionally, the resulting 5 H -benzo[ b ]carbazoles exhibit good fluorescence properties, demonstrating the synthetic practicality of this method. Moreover, control experiments were performed to illustrate the reaction mechanism.

Details

Language :
English
ISSN :
1477-0539
Volume :
22
Issue :
29
Database :
MEDLINE
Journal :
Organic & biomolecular chemistry
Publication Type :
Academic Journal
Accession number :
38993018
Full Text :
https://doi.org/10.1039/d4ob00782d