Iodo-sulphonylation of 1, 6-enynones: a metal-free strategy to synthesize N-substituted succinimides. Issue 40 (30th September 2022)

• Record Type: Journal Article
• Authors: Sivanantham, Mathiyazhagan; Jennifer G, Abigail; Varathan, Elumalai; Ramasamy, Mohankumar; Senadi, Gopal Chandru
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 40(2022)
• Page Start: 7942
• Page End: 7948
• Publication Date: 2022-09-30
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01277d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : I2 -TBHP promoted stereoselective synthesis of iodo-sulfonated succinimides was achieved through a cascade C–C, C–S and C–I bond formation reaction. The synthetic application of the iodo-functionality has been extended to the Heck coupling reaction. Abstract : An iodine-mediated radical cyclization of 1, 6-enynones with sulphonyl hydrazides using tert -butyl hydroperoxide (TBHP) as the oxidant has been developed for the synthesis of iodo-sulphonylated-succinimide derivatives. The notable advantages of the developed method are metal-free conditions, broad functional group tolerance, column chromatography-free purification, high stereoselectivity ( E isomer), shorter reaction times, and the cascade construction of three new bonds (C–S, C–I, and C–C). The synthetic application of the iodo-functionality has been extended to the Heck coupling reaction with acrylonitrile and to the Suzuki coupling reaction with benzene boronic acid.