Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction

A method for the one-step construction of 3,3,4,4-tetrafluorinated piperidines from nitrones and readily accessible tetrafluorinated iodobromobutane is described. The reaction requires an excess amount of ascorbic acid as the terminal reductant and is performed in the presence of an iridium photocat...

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Main Authors:	Vyacheslav I. Supranovich, Igor A. Dmitriev, Alexander D. Dilman
Format:	Article
Language:	English
Published:	Beilstein-Institut 2020-12-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	difluoroalkylation nitrones organofluorine compounds photocatalysis radical addition
Online Access:	https://doi.org/10.3762/bjoc.16.260

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spelling	doaj-484cce9572e84487b34929981e57e2f52021-04-02T18:43:27ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-12-011613104310810.3762/bjoc.16.2601860-5397-16-260Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reactionVyacheslav I. Supranovich0Igor A. Dmitriev1Alexander D. Dilman2N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation,N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation,N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation,A method for the one-step construction of 3,3,4,4-tetrafluorinated piperidines from nitrones and readily accessible tetrafluorinated iodobromobutane is described. The reaction requires an excess amount of ascorbic acid as the terminal reductant and is performed in the presence of an iridium photocatalyst activated by blue light. The annelation is a result of a radical addition at the nitrone, intramolecular nucleophilic substitution, and reduction of the N–O bond.https://doi.org/10.3762/bjoc.16.260difluoroalkylationnitronesorganofluorine compoundsphotocatalysisradical addition
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Vyacheslav I. Supranovich Igor A. Dmitriev Alexander D. Dilman
spellingShingle	Vyacheslav I. Supranovich Igor A. Dmitriev Alexander D. Dilman Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction Beilstein Journal of Organic Chemistry difluoroalkylation nitrones organofluorine compounds photocatalysis radical addition
author_facet	Vyacheslav I. Supranovich Igor A. Dmitriev Alexander D. Dilman
author_sort	Vyacheslav I. Supranovich
title	Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
title_short	Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
title_full	Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
title_fullStr	Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
title_full_unstemmed	Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
title_sort	synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2020-12-01
description	A method for the one-step construction of 3,3,4,4-tetrafluorinated piperidines from nitrones and readily accessible tetrafluorinated iodobromobutane is described. The reaction requires an excess amount of ascorbic acid as the terminal reductant and is performed in the presence of an iridium photocatalyst activated by blue light. The annelation is a result of a radical addition at the nitrone, intramolecular nucleophilic substitution, and reduction of the N–O bond.
topic	difluoroalkylation nitrones organofluorine compounds photocatalysis radical addition
url	https://doi.org/10.3762/bjoc.16.260
work_keys_str_mv	AT vyacheslavisupranovich synthesisoftetrafluorinatedpiperidinesfromnitronesviaavisiblelightpromotedannelationreaction AT igoradmitriev synthesisoftetrafluorinatedpiperidinesfromnitronesviaavisiblelightpromotedannelationreaction AT alexanderddilman synthesisoftetrafluorinatedpiperidinesfromnitronesviaavisiblelightpromotedannelationreaction
_version_	1721551027496288256

Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction

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