Di-tert-butyl Peroxide-Mediated Radical C(sp2/sp3)–S Bond Cleavage and Group-Transfer Cyclization

• DOI: 10.1021/acs.orglett.9b02837
• Publication Date: 2019-09-16T15:46:36Z
• Authors: Kai Luo; Wen-Chao Yang; Kai Wei; Yue Liu; Jun-Ke Wang; Lei Wu
• Keywords: Cleavage (geology); Peroxide; Bond cleavage

A novel strategy of cascade radical C(sp2/sp3)–S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties 2-isocyanoaryl thioethers containing aliphatic, aryl, heteroaromatic groups can be cleaved precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the reaction undertakes an intermolecular pathway, inner sources (R radicals) exhibit high priority over those methyl origin from di-tert-butyl peroxide.