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

Kai Luo, Wen-Chao Yang, Kai Wei, Yue Liu, Jun-Ke Wang and Lei Wu*

*Jiangsu Key Laboratory of Pesticide Science and Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China, Email:

K. Luo, W.-C. Yang, K. Wei, Y. Liu, J.-K. Wang, L. Wu, Org. Lett., 2019, 21, 7851-7856.

DOI: 10.1021/acs.orglett.9b02837

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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.

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proposed mechanism

Key Words

benzothiazoles, DTBP

ID: J54-Y2019