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

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 atte...

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Autores principales: Simonneau, Antoine, Garcia, Pierre, Goddard, Jean-Philippe, Mouriès-Mansuy, Virginie, Malacria, Max, Fensterbank, Louis
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201052/
https://www.ncbi.nlm.nih.gov/pubmed/22043249
http://dx.doi.org/10.3762/bjoc.7.162
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author Simonneau, Antoine
Garcia, Pierre
Goddard, Jean-Philippe
Mouriès-Mansuy, Virginie
Malacria, Max
Fensterbank, Louis
author_facet Simonneau, Antoine
Garcia, Pierre
Goddard, Jean-Philippe
Mouriès-Mansuy, Virginie
Malacria, Max
Fensterbank, Louis
author_sort Simonneau, Antoine
collection PubMed
description 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.
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spelling pubmed-32010522011-10-31 Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles Simonneau, Antoine Garcia, Pierre Goddard, Jean-Philippe Mouriès-Mansuy, Virginie Malacria, Max Fensterbank, Louis Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2011-10-07 /pmc/articles/PMC3201052/ /pubmed/22043249 http://dx.doi.org/10.3762/bjoc.7.162 Text en Copyright © 2011, Simonneau et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Simonneau, Antoine
Garcia, Pierre
Goddard, Jean-Philippe
Mouriès-Mansuy, Virginie
Malacria, Max
Fensterbank, Louis
Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles
title Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles
title_full Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles
title_fullStr Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles
title_full_unstemmed Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles
title_short Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles
title_sort combination of gold catalysis and selectfluor for the synthesis of fluorinated nitrogen heterocycles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201052/
https://www.ncbi.nlm.nih.gov/pubmed/22043249
http://dx.doi.org/10.3762/bjoc.7.162
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