Alkyl Radical Initiated Cyclization/Cascade for Synthesizing Lactam-Substituted Alkyl Sulfones
Li-Jun Wu , Kai-Yi Zhang , Pei Yang , Chuan-Chong Peng , Jin-Hui Liu , Qing Li , Da-Zhi Sun , Shuangfeng Yin
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (16) : 1853 -1859.
Alkyl Radical Initiated Cyclization/Cascade for Synthesizing Lactam-Substituted Alkyl Sulfones
An alkyl radical initiated cyclization/tandem reaction of alkyl bromides and alkyl electrophiles by using potassium metabisulphite (K 2S 2O 5) as a connector is developed for the synthesis of various lactam-substituted alkyl sulfones. Notably, this process does not require a metal catalyst or metal powder reductant, highlighting its environmentally friendly features. The reaction demonstrates outstanding substrate adaptability and a high tolerance towards diverse functional groups. Furthermore, the biologically active molecules and commercially available drugs with a late-stage modification are also highly compatible with this transformation. Mechanistic studies revealed that the reaction proceeds through a single-step process involving intramolecular radical cyclization, “SO 2” insertion, and external alkyl incorporation.
Alkyl radical / Metal-free catalyzed / Cyclization/cascade / Potassium metabisulphite / Electrophiles / Alkyl sulfones / Lactams / Alkyl bromides / Sodium formate
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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