Regioselective (Diacetoxyiodo)benzene-Promoted Halocyclization of Unfunctionalized Olefins

Gong-Qing Liu and Yue-Ming Li*

*College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin 300071, People's Republic of China, Email: ymlinankai.edu.cn

G.-Q. Liu, Y.-M. Li, J. Org. Chem., 2014, 79, 10094-10109.

DOI: 10.1021/jo501739j

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Abstract

In the presence of 1.1 equiv of (Diacetoxyiodo)benzene (PIDA) and suitable halogen sources, a variety of olefins underwent haloamidation, haloetherification, and halolactonization to the corresponding 1,2-bifunctional cyclic skeletons in very good isolated yields. Subsequent mild nucleophilic substitution gives key intermediates for biologically interesting compounds in high yields.

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Preparation of trans-2-Substituted-4-halopiperidines and cis-2-Substituted-4-halotetrahydropyrans via AlCl₃-Catalyzed Prins Reaction

G.-Q. Liu, B. Cui, R. Xu, X.-M. Li, J. Org. Chem., 2016, 81, 5144-5161.

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Key Words

pyrrolidines, piperidines, iodosobenzene diacetate

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ID: J42-Y2014