Literature DB >> 25541887

N-aminopyridinium salts as precursors for N-centered radicals--direct amidation of arenes and heteroarenes.

Tobias W Greulich1, Constantin G Daniliuc, Armido Studer.   

Abstract

Readily prepared N-aminopyridinium salts are valuable precursors for the generation of N-centered radicals. Reduction of these salts by single electron transfer allows for clean generation of amidyl radicals. It is shown that direct radical C-H amination of heteroarenes and arenes can be achieved with N-aminopyridinium salts under mild conditions by using photoredox catalysis.

Entities:  

Year:  2014        PMID: 25541887     DOI: 10.1021/ol503338b

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  18 in total

1.  Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

Authors:  Nicholas L Reed; Madeline I Herman; Vladimir P Miltchev; Tehshik P Yoon
Journal:  Org Lett       Date:  2018-11-08       Impact factor: 6.005

2.  Mechanism and Dynamics of Intramolecular C-H Insertion Reactions of 1-Aza-2-azoniaallene Salts.

Authors:  Xin Hong; Daniel A Bercovici; Zhongyue Yang; Nezar Al-Bataineh; Ramya Srinivasan; Ram C Dhakal; K N Houk; Matthias Brewer
Journal:  J Am Chem Soc       Date:  2015-07-07       Impact factor: 15.419

3.  Selective Modification of Tryptophan Residues in Peptides and Proteins Using a Biomimetic Electron Transfer Process.

Authors:  Samantha J Tower; Wesley J Hetcher; Tyler E Myers; Nicholas J Kuehl; Michael T Taylor
Journal:  J Am Chem Soc       Date:  2020-05-05       Impact factor: 15.419

4.  Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.

Authors:  Corey H Basch; Jennie Liao; Jianyu Xu; Jacob J Piane; Mary P Watson
Journal:  J Am Chem Soc       Date:  2017-04-05       Impact factor: 15.419

Review 5.  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

6.  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

7.  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 8.  Photoredox-Catalyzed C-H Functionalization Reactions.

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

9.  Catalytic N-radical cascade reaction of hydrazones by oxidative deprotonation electron transfer and TEMPO mediation.

Authors:  Xiao-Qiang Hu; Xiaotian Qi; Jia-Rong Chen; Quan-Qing Zhao; Qiang Wei; Yu Lan; Wen-Jing Xiao
Journal:  Nat Commun       Date:  2016-04-06       Impact factor: 14.919

10.  Sterically Congested 2,6-Disubstituted Anilines from Direct C-N Bond Formation at an Iodine(III) Center.

Authors:  Nicola Lucchetti; Michelangelo Scalone; Serena Fantasia; Kilian Muñiz
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

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