Metal-free intramolecular aminofluorination of alkenes mediated by PhI(OPiv)2/hydrogen fluoride-pyridine system.

Qing Wang, Wenhe Zhong, Xiong Wei, Maoheng Ning, Xiangbao Meng, Zhongjun Li

The State Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, PR China.

Organic & biomolecular chemistry 2012 Nov 21

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A convenient, metal-free intramolecular aminofluorination of alkenes has been developed. Employing readily available PhI(OPiv)(2) and hydrogen fluoride-pyri dine in the presence of BF(3)·OEt(2), tosyl-protected pent-4-en-1-amines were converted to 3-F-piperidines in one step in good yields as well as high stereoselectivity.

Citation

Qing Wang, Wenhe Zhong, Xiong Wei, Maoheng Ning, Xiangbao Meng, Zhongjun Li. Metal-free intramolecular aminofluorination of alkenes mediated by PhI(OPiv)2/hydrogen fluoride-pyridine system. Organic & biomolecular chemistry. 2012 Nov 21;10(43):8566-9