Key Lab of Functional Molecular Engineering of Guangdong Province, State Key Laboratory of Luminescent Materials and Devices, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.
Chem Commun (Camb). 2022 Jun 1;58(45):6522-6525. doi: 10.1039/d2cc00958g.
Herein, a straightforward method for the synthesis of 2,5-disubstituted selenophenes [2+2+1] cyclization of easily accessible terminal alkynes and elemental selenium has been developed. This reaction features high atom- and step-economy, excellent regioselectivity, good functional group tolerance and the use of stable and non-toxic selenium as a selenium source. A series of control experiments suggests that the reaction might undergo Glaser coupling reaction of two molecules of alkynes, followed by insertion of HSe and subsequent cyclization. Moreover, the newly formed products can be further converted to diverse conjugated selenophene-based derivatives, demonstrating their potential applications in organic synthesis and materials science.
本文开发了一种通过易得的末端炔烃和元素硒的[2+2+1]环化反应来合成 2,5-取代硒吩的简便方法。该反应具有原子经济性和步骤经济性高、区域选择性好、官能团容忍度好以及使用稳定无毒的硒作为硒源等优点。一系列控制实验表明，该反应可能经历两个炔烃分子的Glaser 偶联反应，然后是 HSe 的插入和随后的环化。此外，新形成的产物可以进一步转化为各种共轭硒吩基衍生物，这证明了它们在有机合成和材料科学中的潜在应用。
