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

doi:10.1039/C2OB26664D

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

Qing Wang,^a Wenhe Zhong,^a Xiong Wei,^a Maoheng Ning,^a Xiangbao Meng*^a and Zhongjun Li*^a

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* Corresponding authors

^a The State Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. China
E-mail: xbmeng@bjmu.edu.cn, zjli@bjmu.edu.cn

Abstract

A convenient, metal-free intramolecular aminofluorination of alkenes has been developed. Employing readily available PhI(OPiv)₂ and hydrogen fluoride–pyridine in the presence of BF₃·OEt₂, tosyl-protected pent-4-en-1-amines were converted to 3-F-piperidines in one step in good yields as well as high stereoselectivity.

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Article information

DOI: https://doi.org/10.1039/C2OB26664D
Article type: Communication
Submitted: 23 Aug 2012
Accepted: 11 Sep 2012
First published: 12 Sep 2012

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Org. Biomol. Chem., 2012,10, 8566-8569

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

Q. Wang, W. Zhong, X. Wei, M. Ning, X. Meng and Z. Li, Org. Biomol. Chem., 2012, 10, 8566 DOI: 10.1039/C2OB26664D

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Organic & Biomolecular Chemistry