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Iodo-sulphonylation of 1,6-enynones: a metal-free strategy to synthesize N-substituted succinimides.
Org Biomol Chem
; 20(40): 7942-7948, 2022 10 19.
Artigo
em Inglês
| MEDLINE
| ID: mdl-36178240
RESUMO
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.