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

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.

SUBMITTER: Simonneau A

PROVIDER: S-EPMC3201052 | biostudies-other | 2011

REPOSITORIES: biostudies-other

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

Simonneau Antoine A Garcia Pierre P Goddard Jean-Philippe JP Mouriès-Mansuy Virginie V Malacria Max M Fensterbank Louis L

Beilstein journal of organic chemistry 20111007

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 ...[more]

PMID: 22043249

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