Di-tert-butyl Peroxide-Mediated Radical C(sp2/sp3)–S Bond Cleavage and Group-Transfer Cyclization
- Kai LuoKai LuoJiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaMore by Kai Luo,
- Wen-Chao YangWen-Chao YangInstitute of Pesticide, School of Horticulture and Plant Protection, Yangzhou University, Yangzhou 225009, ChinaMore by Wen-Chao Yang,
- Kai WeiKai WeiJiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaMore by Kai Wei,
- Yue LiuYue LiuJiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaMore by Yue Liu,
- Jun-Ke WangJun-Ke WangJiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaMore by Jun-Ke Wang, and
- Lei Wu*Lei Wu*E-mail: [email protected]Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaMore by Lei Wu
Abstract
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.
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