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Beilstein-Institut, Beilstein Journal of Organic Chemistry, (7), p. 1379-1386, 2011

DOI: 10.3762/bjoc.7.162

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Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles

Journal article published in 2011 by Antoine Simonneau ORCID, Pierre Garcia, Jean-Philippe Goddard, Virginie Mouriès-Mansuy ORCID, Max Malacria, Louis Fensterbank
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

We herein report the synthesis of 3-fluoro-2-methylene-pyrrolidine (3a) and -piperidine (3b) from 1,5- and 1,6-aminoalkynes, respectively, using a combination of a gold-catalyzed hydroamination reaction followed by electrophilic trapping of an intermediate cyclic enamine by Selectfluor. Careful attention was paid to the elucidation of the mechanism and Selectfluor was suggested to play the double role of promoting the oxidation of gold(I) to a gold(III) active species and also the electrophilic fluorination of the enamine intermediates.