Literature DB >> 33437323

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

Vyacheslav I Supranovich1, Igor A Dmitriev1,2, Alexander D Dilman1.   

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.
Copyright © 2020, Supranovich et al.; licensee Beilstein-Institut.

Entities:  

Keywords:  difluoroalkylation; nitrones; organofluorine compounds; photocatalysis; radical addition

Year:  2020        PMID： 33437323      PMCID： PMC7783028          DOI： 10.3762/bjoc.16.260

Source DB:  PubMed          Journal:  Beilstein J Org Chem        ISSN： 1860-5397            Impact factor:   2.883


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