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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Main Authors:	Antoine Simonneau, Pierre Garcia, Jean-Philippe Goddard, Virginie Mouriès-Mansuy, Max Malacria, Louis Fensterbank
Format:	Article
Language:	English
Published:	Beilstein-Institut 2011-10-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	cycloisomerization reactions fluorinated pyrrolidines gold catalysis Selectfluor
Online Access:	https://doi.org/10.3762/bjoc.7.162

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spelling	doaj-179b48695e844b008f57d98b7915dfbb2021-02-02T05:48:23ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-10-01711379138610.3762/bjoc.7.1621860-5397-7-162Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocyclesAntoine Simonneau0Pierre Garcia1Jean-Philippe Goddard2Virginie Mouriès-Mansuy3Max Malacria4Louis Fensterbank5UPMC Univ Paris 06, Sorbonne Universités, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, FranceUPMC Univ Paris 06, Sorbonne Universités, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, FranceUPMC Univ Paris 06, Sorbonne Universités, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, FranceUPMC Univ Paris 06, Sorbonne Universités, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, FranceUPMC Univ Paris 06, Sorbonne Universités, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, FranceUPMC Univ Paris 06, Sorbonne Universités, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, FranceWe 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.https://doi.org/10.3762/bjoc.7.162cycloisomerization reactionsfluorinated pyrrolidinesgold catalysisSelectfluor
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Antoine Simonneau Pierre Garcia Jean-Philippe Goddard Virginie Mouriès-Mansuy Max Malacria Louis Fensterbank
spellingShingle	Antoine Simonneau Pierre Garcia Jean-Philippe Goddard Virginie Mouriès-Mansuy Max Malacria Louis Fensterbank Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles Beilstein Journal of Organic Chemistry cycloisomerization reactions fluorinated pyrrolidines gold catalysis Selectfluor
author_facet	Antoine Simonneau Pierre Garcia Jean-Philippe Goddard Virginie Mouriès-Mansuy Max Malacria Louis Fensterbank
author_sort	Antoine Simonneau
title	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_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_sort	combination of gold catalysis and selectfluor for the synthesis of fluorinated nitrogen heterocycles
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2011-10-01
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.
topic	cycloisomerization reactions fluorinated pyrrolidines gold catalysis Selectfluor
url	https://doi.org/10.3762/bjoc.7.162
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Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles

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