Jiang You-Qin, Wang Yong-Hao, Zhou Chen-Fan, Zhang Yun-Qian, Ling Yong, Zhao Yu, Liu Gong-Qing
School of Pharmacy and Jiangsu Province Key Laboratory for Inflammation and Molecular Drug Target, Nantong University, Nantong 226019, People's Republic of China.
J Org Chem. 2022 Nov 4;87(21):14609-14622. doi: 10.1021/acs.joc.2c01989. Epub 2022 Oct 25.
Intermolecular carboselenenylation of easily accessible alkenes by utilizing diselenides and -fluorobenzenesulfonimide (NFSI) under metal-free and mild conditions is reported. Preliminary mechanistic studies indicate that the oxidation of diselenide by NFSI through a single-electron-transfer process produces an active selenenyl cationic radical species that initiates the intermolecular carboselenenylation of olefins, forming key Se-C and C-C bonds. Under optimized conditions, a broad spectrum of functionally and structurally diverse selenoether derivatives with promising yields is accessed with a very high functional group tolerance.
报道了在无金属温和条件下，利用二硒化物和N-氟苯磺酰亚胺（NFSI）对易于获得的烯烃进行分子间碳硒化反应。初步机理研究表明，NFSI通过单电子转移过程氧化二硒化物生成活性硒烯基阳离子自由基物种，该物种引发烯烃的分子间碳硒化反应，形成关键的Se-C和C-C键。在优化条件下，可获得功能和结构多样的硒醚衍生物，产率可观，且对官能团具有很高的耐受性。
