Construction of diverse C-S/C-Se bonds via nickel catalyzed reductive coupling employing thiosulfonates and a selenosulfonate under mild conditions

• Published in: ORGANIC CHEMISTRY FRONTIERS Vol. 9; no. 5; pp. 1375 - 1382
• Main Authors: Liu, Yong, Xing, Shuya, Zhang, Jing, Liu, Wen, Xu, Yuenian, Zhang, Yan, Yang, Kefang, Yang, Lei, Jiang, Kezhi, Shao, Xinxin
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 01.03.2022; Royal Society of Chemistry
• Subjects: Catalysts; Chemistry; Chemistry, Organic; Cross coupling; Functional groups; Iodides; Nickel; Organic chemistry; Physical Sciences; Science & Technology; Selectivity; Thioethers; HALIDES; THIOLS; CARBON; REAGENTS; LIGANDS; SULFIDES; ARYL IODIDES; SULFUR; THIOARYLATION; CLEAVAGE
• DOI: 10.1039/d1qo01873f
• ISSN: 2052-4129; 2052-4110

A nickel-catalyzed reductive cross coupling between organic iodides and thiosulfonates and a selenosulfonate under mild conditions is disclosed. This practical method provides a facile access to a series of unsymmetrical thioethers with low catalyst loading, good functional group tolerance, and excellent chemo-selectivity. Notably, the synthetic applications of the approach feature scaling-up of reactions, late-stage modification of pharmaceuticals, and preparation of various useful targeted compounds, including sulfoximine, bipyridine, and vortioxetine. Primary mechanistic studies showed that a radical pathway was involved. Moreover, diverse C-S/C-Se bond formations were achieved under mild reaction conditions.