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Modular Preparation of 5-Halomethyl-2-oxazolines via PhI(OAc)2-Promoted Intramolecular Halooxygenation of N-Allylcarboxamides

Gong-Qing Liu, Chun-Hua Yang and Yue-Ming Li*

*State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071, People's Republic of China, Email:

G.-Q. Liu, C.-H. Yang, Y.-M. Li, J. Org. Chem., 2015, 80, 11339-113550.

DOI: 10.1021/acs.joc.5b01832 (free Supporting Information)

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Intramolecular halooxygenation and halothionation of N-allylcarboxamides/N-allylcarbothioamides proceeded readily in the presence of (diacetoxyiodo)benzene (PIDA) as the reaction promoter and halotrimethylsilane as the halogen source, providing the corresponding 5-halomethyloxazolines/5-halomethylthiazolines in very good yields. The 5-halomethyl products could be converted to different derivatives via nucleophilic substitution.

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Key Words

Oxazolines, PIDA

ID: J42-Y2015