Graphene oxide-catalyzed synthesis of benzothiazoles with amines and elemental sulfur via oxidative coupling strategy of amines to imines

The graphene oxide-catalyzed coupling and cyclization reactions of primary amines with elemental sulfur was developed to afford various optically property benzothiazoles. This coupling and cyclization strategies proceeded under the oxidant system graphene oxide/O2 and constructed carbon-heteroatom (...

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Bibliographic Details
Published in:Tetrahedron 2022-01, Vol.106-107, p.132624, Article 132624
Main Authors: He, Haiping, Duan, Dehao, Li, Hong, Wei, Yifei, Nie, Liang, Tang, Bo, Wang, Hanyu, Han, Xiaowei, Huang, Panpan, Peng, Xiangjun
Format: Article
Language:English
Subjects:
Aggregation-induced emission
Amines
Benzothiazoles
Graphene oxide
Oxidative coupling strategy
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Summary:The graphene oxide-catalyzed coupling and cyclization reactions of primary amines with elemental sulfur was developed to afford various optically property benzothiazoles. This coupling and cyclization strategies proceeded under the oxidant system graphene oxide/O2 and constructed carbon-heteroatom (N, S) bonds with amines and elemental sulfur. Due to benzothiazoles as common chromophores, these products exhibited intriguing fluorescence properties, including outstanding Stokes shifts (up to 161 nm) and quantum yields (up to 74%). Utilizing the products’ unique fluorescence response in different solvents, β-naphthothiazole 4a showed excellent aggregation-induced emission properties in 1,2-dichloroethane, which was 60 times higher than in tetrahydrofuran. [Display omitted] •The GO-catalyzed cyclization of primary amines with sulfur.•Highly green and practical.•Good regioselectivity and high atom economy.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2021.132624