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

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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Bibliographic Details
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
Description
Summary: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.
ISSN:1860-5397

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