期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 17, 期 8, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202101394
关键词
Green chemistry; Heterocycle; Organochalcogen; photocyclization; benzo[b]chalcogenophene
资金
- UFPel, IFSul
- FAPERGS [PqG 19/2551-0001867-3, PROPESP-IFSul/PE04210621/057]
- CNPq [436483/2018-1]
- FINEP
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior - Brasil (CAPES) [001]
A metal- and catalyst-free photo-promoted cyclization method using UVA irradiation was developed to synthesize new C3-unsubstituted 2-selanyl benzochalcogenophenes, which can be easily functionalized under natural sunlight irradiation. The solvent used in the reaction can be reused multiple times.
A metal- and catalyst-free photo-promoted cyclization of properly substituted vinyl selenides was developed using UVA irradiation. A total of eighteen new C3-unsubstituted 2-selanyl benzochalcogenophenes (benzofurans, benzothiophenes and benzoselenophenes) were prepared in 30-86% yield after irradiation with UVA at room temperature. The usefulness of the title compounds was demonstrated in the easy functionalization of the remaining free C-H bond of the benzochalcogenophenes to form new C-Se and C-Br bonds by simple procedures. Furthermore, the reaction can be performed under natural sunlight irradiation and the solvent is easily reused further in several subsequent runs.
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