Literature DB >> 24912622

Organic azides: "energetic reagents" for the intermolecular amination of C-H bonds.

Daniela Intrieri1, Paolo Zardi, Alessandro Caselli, Emma Gallo.   

Abstract

This feature article provides an overview of the application of organic azides for the intermolecular amination of sp(3) and sp(2) C-H bonds. The catalytic activity of several metal complexes was reviewed underlining both synthetic and mechanistic aspects of the C-H amination. The majority of the aminated compounds reported in literature have been collected in this paper to provide a compendium of published procedures. In addition, the discussion of involved mechanisms has been included to assist the reader to envisage the future potential of organic azides in the synthesis of aza-derivatives.

Entities:  

Year:  2014        PMID: 24912622     DOI: 10.1039/c4cc03016h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  12 in total

1.  Characterization of Porphyrin-Co(III)-'Nitrene Radical' Species Relevant in Catalytic Nitrene Transfer Reactions.

Authors:  Monalisa Goswami; Volodymyr Lyaskovskyy; Sérgio R Domingos; Wybren Jan Buma; Sander Woutersen; Oliver Troeppner; Ivana Ivanović-Burmazović; Hongjian Lu; Xin Cui; X Peter Zhang; Edward J Reijerse; Serena DeBeer; Matti M van Schooneveld; Florian Felix Pfaff; Kallol Ray; Bas de Bruin
Journal:  J Am Chem Soc       Date:  2015-04-16       Impact factor: 15.419

2.  Ir-Catalyzed Intermolecular Branch-Selective Allylic C-H Amidation of Unactivated Terminal Olefins.

Authors:  Honghui Lei; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-02-04       Impact factor: 15.419

Review 3.  Transition Metal Catalysis Controlled by Hydrogen Bonding in the Second Coordination Sphere.

Authors:  Joost N H Reek; Bas de Bruin; Sonja Pullen; Tiddo J Mooibroek; Alexander M Kluwer; Xavier Caumes
Journal:  Chem Rev       Date:  2022-05-20       Impact factor: 72.087

4.  Traceless Benzylic C-H Amination via Bifunctional N-Aminopyridinium Intermediates.

Authors:  Pritam Roychowdhury; Roberto G Herrera; Hao Tan; David C Powers
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-20       Impact factor: 16.823

5.  Rhodium(ii)-catalyzed C-H aminations using N-mesyloxycarbamates: reaction pathway and by-product formation.

Authors:  Emna Azek; Maroua Khalifa; Johan Bartholoméüs; Matthias Ernzerhof; Hélène Lebel
Journal:  Chem Sci       Date:  2018-10-22       Impact factor: 9.825

6.  Cobalt-Porphyrin-Catalysed Intramolecular Ring-Closing C-H Amination of Aliphatic Azides: A Nitrene-Radical Approach to Saturated Heterocycles.

Authors:  Petrus F Kuijpers; Martijn J Tiekink; Willem B Breukelaar; Daniël L J Broere; Nicolaas P van Leest; Jarl Ivar van der Vlugt; Joost N H Reek; Bas de Bruin
Journal:  Chemistry       Date:  2017-05-02       Impact factor: 5.236

7.  Catalytic Synthesis of N-Heterocycles via Direct C(sp3)-H Amination Using an Air-Stable Iron(III) Species with a Redox-Active Ligand.

Authors:  Bidraha Bagh; Daniël L J Broere; Vivek Sinha; Petrus F Kuijpers; Nicolaas P van Leest; Bas de Bruin; Serhiy Demeshko; Maxime A Siegler; Jarl Ivar van der Vlugt
Journal:  J Am Chem Soc       Date:  2017-03-28       Impact factor: 15.419

Review 8.  Metal-Catalysed Azidation of Organic Molecules.

Authors:  Monalisa Goswami; Bas de Bruin
Journal:  European J Org Chem       Date:  2016-12-22

9.  Porphyrin Cobalt(III) "Nitrene Radical" Reactivity; Hydrogen Atom Transfer from Ortho-YH Substituents to the Nitrene Moiety of Cobalt-Bound Aryl Nitrene Intermediates (Y = O, NH).

Authors:  Monalisa Goswami; Christophe Rebreyend; Bas de Bruin
Journal:  Molecules       Date:  2016-02-20       Impact factor: 4.411

10.  Revisiting the Electronic Structure of Cobalt Porphyrin Nitrene and Carbene Radicals with NEVPT2-CASSCF Calculations: Doublet versus Quartet Ground States.

Authors:  Nicolaas P van Leest; Bas de Bruin
Journal:  Inorg Chem       Date:  2021-06-05       Impact factor: 5.165

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