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

ABSTRACT: 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.

SUBMITTER: Supranovich VI 

PROVIDER: S-EPMC7783028 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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

Supranovich Vyacheslav I VI   Dmitriev Igor A IA   Dilman Alexander D AD  

Beilstein journal of organic chemistry 20201229

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. ...[more]

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