Literature DB >> 29143478

Regio- and Stereoselective Iron-Catalyzed Oxyazidation of Enamides Using a Hypervalent Iodine Reagent.

Sylvain Bertho1, Romain Rey-Rodriguez1, Cyril Colas1, Pascal Retailleau2, Isabelle Gillaizeau1.   

Abstract

A novel regio- and diastereoselective iron-catalyzed intermolecular oxyazidation of enamides using various azidobenziodoxolone (ABX) derivatives is presented. A variety of α-N3 amino derivatives and of α-N3 piperidines were synthesized in good yields and under mild reaction conditions. The reaction involves a radical process using cheap FeCl2 as the initiator.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  azides; heterocycles; hypervalent iodine; iron catalysis; radicals

Year:  2017        PMID： 29143478     DOI： 10.1002/chem.201704499

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  6 in total

Review 1.  Atom-economical group-transfer reactions with hypervalent iodine compounds.

Authors:  Andreas Boelke; Peter Finkbeiner; Boris J Nachtsheim
Journal:  Beilstein J Org Chem       Date:  2018-05-30       Impact factor: 2.883

2.  Synthesis of FeIII and FeIV Cyanide Complexes Using Hypervalent Iodine Reagents as Cyano-Transfer One-Electron Oxidants.

Authors:  Charafa Souilah; Sergio A V Jannuzzi; Derya Demirbas; Sergei Ivlev; Marcel Swart; Serena DeBeer; Alicia Casitas
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-29       Impact factor: 16.823

3.  Photocatalytic Umpolung of N- and O-substituted alkenes for the synthesis of 1,2-amino alcohols and diols.

Authors:  Stephanie G E Amos; Stefano Nicolai; Jerome Waser
Journal:  Chem Sci       Date:  2020-09-22       Impact factor: 9.825

Review 4.  Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis.

Authors:  Gwendal Grelier; Benjamin Darses; Philippe Dauban
Journal:  Beilstein J Org Chem       Date:  2018-06-21       Impact factor: 2.883

5.  Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions.

Authors:  Hideyasu China; Nami Kageyama; Hotaka Yatabe; Naoko Takenaga; Toshifumi Dohi
Journal:  Molecules       Date:  2021-03-27       Impact factor: 4.411

Review 6.  Iron-catalyzed domino coupling reactions of π-systems.

Authors:  Austin Pounder; William Tam
Journal:  Beilstein J Org Chem       Date:  2021-12-07       Impact factor: 2.883
  6 in total

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