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

Organic & biomolecular chemistry (2012-09-26)
Qing Wang, Wenhe Zhong, Xiong Wei, Maoheng Ning, Xiangbao Meng, Zhongjun Li
RESUMEN

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 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.

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Sigma-Aldrich
Hydrofluoric acid, ACS reagent, 48%
Sigma-Aldrich
Hydrofluoric acid, 48 wt. % in H2O, ≥99.99% trace metals basis
Sigma-Aldrich
Hydrofluoric acid, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥48%