Di- tert-butyl Peroxide-Mediated Radical C(sp2/sp3)-S Bond Cleavage and Group-Transfer Cyclization
A novel strategy of cascade radical C(sp2/sp3)-S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway, and the inner radical sources (R radicals) exhibit high priority over those of methyl radical origin from di-tert-butyl peroxide.
Luo, Kai,Yang, Wen-Chao,Wei, Kai,Liu, Yue,Wang, Jun-Ke,Wu, Lei
p. 7851 - 7856
(2019/10/11)
AIBN-Promoted Synthesis of Bibenzo[ b][1,4]thiazines by the Condensation of 2,2′-Dithiodianiline with Methyl Aryl Ketones
A series of bibenzo[b][1,4]thiazines with various functional groups has been synthesized by a free-radical condensation reaction. Bibenzo[b][1,4]thiazines were obtained in moderate to good yield (up to 85%) through a one-step reaction of readily available 2,2′-dithiodianiline and methyl aryl ketones with AIBN as radical initiator in HOAc. Bibenzo[b][1,4]thiazines exhibit diversiform solid-state packing.