Access to disulfides through ligand-controlled nickel-catalyzed dithiosulfonate and alkyl halides

• Published in: ORGANIC CHEMISTRY FRONTIERS Vol. 11; no. 3; pp. 830 - 835
• Main Authors: Chen, Wang, Liu, Xin-yu, Sheng, Daopeng, Jiang, Yi-Fan, Rao, Weidong, Shen, Shu-Su, Yang, Zhao-Ying, Wang, Shun-Yi
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 30.01.2024; Royal Society of Chemistry
• Subjects: Alkanes; Anti-inflammatory agents; Chemical reactions; Chemistry; Chemistry, Organic; Cross coupling; Disulfides; Functional groups; Gout; Halides; Indomethacin; Inflammation; Ligands; Nickel; Phenylalanine; Physical Sciences; Science & Technology; Substrates; DRUG; DESIGN; THIOREDOXIN
• ISSN: 2052-4129; 2052-4110; 2052-4110
• DOI: 10.1039/d3qo01868g

A nickel-catalyzed C-SS reductive cross-coupling reaction of dithiosulfonate and unactivated alkyl halides for producing unsymmetric disulfides is developed. Ligands can greatly promote the conversion or inhibition of the occurrence of reactions, hence the selection of ligands is very important. In this approach, 1-10-phen can maximize the promotion of the reaction. The approach features the unprecedented use of dithiosulfonate in reductive cross-coupling chemistry and is highlighted by the broad substrate scope under mild conditions with excellent functional group tolerance. The approach is applicable to different halogenated alkanes. It is worth noting that the reaction is also applicable to the later modification of the anti-inflammatory drug indomethacin, the anti gout drug probenecid, and Boc-l-phenylalanine. Nickel-catalyzed C-SS reductive cross-coupling reaction of dithiosulfonate and unactivated alkyl halides for producing unsymmetric disulfides with broad substrate scope under mild conditions and with excellent functional group tolerance.