Literature DB >> 30398683

Pyridyl Radical Cation for C-H Amination of Arenes.

Simon L Rössler1, Benson J Jelier2, Pascal F Tripet2, Andrej Shemet1, Gunnar Jeschke3, Antonio Togni2, Erick M Carreira1.   

Abstract

Electron-transfer photocatalysis provides access to the elusive and unprecedented N-pyridyl radical cation from selected N-substituted pyridinium reagents. The resulting C(sp2 )-H functionalization of (hetero)arenes furnishes versatile intermediates for the development of valuable aminated aryl scaffolds. Mechanistic studies that include the first spectroscopic evidence of a spin-trapped N-pyridyl radical adduct implicate SET-triggered, pseudo-mesolytic cleavage of the N-X pyridinium reagents mediated by visible light.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amination; late-stage functionalization; photoredox catalysis; pyridyl radical cation; radical mechanism

Year:  2018        PMID： 30398683     DOI： 10.1002/anie.201810261

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  11 in total

Review 1.  Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors:  Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 60.622

2.  Diversification of Amidyl Radical Intermediates Derived from C-H Aminopyridylation.

Authors:  Asim Maity; Pritam Roychowdhury; Roberto G Herrera; David C Powers
Journal:  Org Lett       Date:  2022-04-04       Impact factor: 6.072

3.  N-Aminopyridinium reagents as traceless activating groups in the synthesis of N-Aryl aziridines.

Authors:  Hao Tan; Samya Samanta; Asim Maity; Pritam Roychowdhury; David C Powers
Journal:  Nat Commun       Date:  2022-06-10       Impact factor: 17.694

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

Review 5.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

6.  Late-Stage Amination of Drug-Like Benzoic Acids: Access to Anilines and Drug Conjugates through Directed Iridium-Catalyzed C-H Activation.

Authors:  Erik Weis; Magnus J Johansson; Belén Martín-Matute
Journal:  Chemistry       Date:  2021-11-17       Impact factor: 5.020

7.  Accelerating fragment-based library generation by coupling high-performance photoreactors with benchtop analysis.

Authors:  Quentin Lefebvre; Christophe Salomé; Thomas C Fessard
Journal:  Beilstein J Org Chem       Date:  2020-05-12       Impact factor: 2.883

8.  Cu(OTf)2 -Mediated Cross-Coupling of Nitriles and N-Heterocycles with Arylboronic Acids to Generate Nitrilium and Pyridinium Products*.

Authors:  Nicola L Bell; Chao Xu; James W B Fyfe; Julien C Vantourout; Jeremy Brals; Sonia Chabbra; Bela E Bode; David B Cordes; Alexandra M Z Slawin; Thomas M McGuire; Allan J B Watson
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-26       Impact factor: 15.336

9.  Practical and Selective sp3 C-H Bond Chlorination via Aminium Radicals.

Authors:  Alastair J McMillan; Martyna Sieńkowska; Piero Di Lorenzo; Gemma K Gransbury; Nicholas F Chilton; Michela Salamone; Alessandro Ruffoni; Massimo Bietti; Daniele Leonori
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-25       Impact factor: 15.336

10.  Impact of substitution on reactions and stability of one-electron oxidised phenyl sulfonates in aqueous solution.

Authors:  Tamas Nemeth; Tym de Wild; Lorenz Gubler; Thomas Nauser
Journal:  Phys Chem Chem Phys       Date:  2022-01-04       Impact factor: 3.676
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