LASOL-CCQFA, Universidade Federal de Pelotas - UFPel, P.O. Box 354, 96010-900, Pelotas, RS, Brazil.
Departamento de Química, Universidade Federal de Santa Maria - UFSM, CEP: 97105-900, Santa Maria - RS, Brazil.
Org Biomol Chem. 2021 Jan 28;19(3):596-604. doi: 10.1039/d0ob02362k.
We describe herein an alternative and transition-metal-free procedure for the access of benzo[b]chalcogenophenes fused to selenophenes via intramolecular cyclization of 1,3-diynes. This efficient protocol involves a double cyclization of 1,3-diynyl chalcogen derivatives promoted by the electrophilic species of organoselenium generated in situ by the oxidative cleavage of the Se-Se bond of dibutyl diselenide using Oxone® in acetonitrile as solvent in an open-flask at 80 °C. In this study, 15 selenophenes with broad substrate scope were prepared in moderate to excellent yields (55-98%) with short reaction times (0.5-3.0 h).
我们在此描述了一种替代的、无需过渡金属的方法，用于通过 1,3-二炔的分子内环化来合成苯并[b]杂环并硒吩。该有效的方案涉及 1,3-二炔基杂环衍生物的双重环化，该环化由二丁基二硒醚的 Se-Se 键的氧化裂解原位生成的有机硒的亲电物种促进，在敞开式烧瓶中、在 80°C 下、以 Oxone®为溶剂、在乙腈中进行。在这项研究中，制备了 15 种具有广泛底物范围的硒吩，产率中等至优秀（55-98%），反应时间短（0.5-3.0 h）。
