Literature DB >> 24964153

Visible-light-promoted redox neutral C-H amidation of heteroarenes with hydroxylamine derivatives.

Qixue Qin1, Shouyun Yu.   

Abstract

A room temperature redox neutral direct C-H amidation of heteroarenes has been achieved. Hydroxylamine derivatives, which are easily accessed, have been employed as tunable nitrogen sources. These reactions were enabled by a visible-light-promoted single-electron transfer pathway without a directing group. A variety of heteroarenes, such as indoles, pyrroles, and furans, could go through this amidation with high yields (up to 98%). These reactions are highly regioselective, and all the products were isolated as a single regioisomer.

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Year:  2014        PMID: 24964153     DOI: 10.1021/ol501457s

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


  12 in total

1.  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

Review 2.  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

3.  Advances in Photocatalysis: A Microreview of Visible Light Mediated Ruthenium and Iridium Catalyzed Organic Transformations.

Authors:  Jon I Day; Kip Teegardin; Jimmie Weaver; John Chan
Journal:  Org Process Res Dev       Date:  2016-06-28       Impact factor: 3.317

Review 4.  Photoredox-Catalyzed C-H Functionalization Reactions.

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

5.  Teaching Old Compounds New Tricks: DDQ-Photocatalyzed C-H Amination of Arenes with Carbamates, Urea, and N-Heterocycles.

Authors:  Somnath Das; Palani Natarajan; Burkhard König
Journal:  Chemistry       Date:  2017-12-07       Impact factor: 5.236

6.  Visible light C-H amidation of heteroarenes with benzoyl azides.

Authors:  E Brachet; T Ghosh; I Ghosh; B König
Journal:  Chem Sci       Date:  2014-10-30       Impact factor: 9.825

7.  Electrocatalytic redox neutral [3 + 2] annulation of N-cyclopropylanilines and alkenes.

Authors:  Qi Wang; Qile Wang; Yuexiang Zhang; Yasmine M Mohamed; Carlos Pacheco; Nan Zheng; Richard N Zare; Hao Chen
Journal:  Chem Sci       Date:  2020-11-09       Impact factor: 9.825

8.  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

9.  Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions.

Authors:  Jacob Davies; Samuel G Booth; Stephanie Essafi; Robert A W Dryfe; Daniele Leonori
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-28       Impact factor: 15.336

10.  Synthesis of Arylamines via Aminium Radicals.

Authors:  Thomas D Svejstrup; Alessandro Ruffoni; Fabio Juliá; Valentin M Aubert; Daniele Leonori
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-24       Impact factor: 15.336

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