Copper-catalyzed regioselective C2–H chlorination of indoles with para-toluenesulfonyl chloride. Issue 23 (1st June 2022)

• Record Type: Journal Article
• Authors: Li, Xue-Hong; Yang, Guang-Chao; Gong, Jun-Fang; Song, Mao-Ping
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 23(2022)
• Page Start: 4815
• Page End: 4825
• Publication Date: 2022-06-01
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00758d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A copper-catalyzed regioselective C2–H chlorination of indoles with para -toluenesulfonyl chloride (TsCl) is developed. Control experiments suggested that intermolecular single-electron-transfer processes might be involved in the reactions. Abstract : A copper-catalyzed, pyrimidine directed regioselective C–H chlorination of indoles with para -toluenesulfonyl chloride (TsCl) has been developed. The reactions proceeded smoothly in the presence of 20 mol% of Cu(OAc)2 as the catalyst and TsCl as the chlorine source, delivering C2-chlorinated indoles with structural diversity in moderate to excellent yields. Mechanistic studies suggested that single electron transfer (SET) from Cu(ii ) to TsCl accompanied by the release of the p -toluenesulfonyl radical and the related Cu(iii )Cl species might be involved in the reactions.