Literature DB >> 27599166

Visible-Light-Induced Direct Oxidative C-H Amidation of Heteroarenes with Sulfonamides.

Kun Tong1, Xiaodong Liu1, Yan Zhang2, Shouyun Yu3.   

Abstract

A direct oxidative C-H amidation of heteroarenes with sulfonamides via nitrogen-centered radicals has been achieved. Nitrogen-centered radicals are directly generated from oxidative cleavage of N-H bonds under visible-light photoredox catalysis. Sulfonamides, which are easily accessed, are used as tunable nitrogen sources and bleach (aqueous NaClO solution) is used as the oxidant. A variety of heteroarenes, including indoles, pyrroles and benzofurans, can undergo this amidation with high yields (up to 92 %). These reactions are highly regioselective, and all the products are isolated as single regioisomer.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H amidation; heterocycles; nitrogen-centered radicals; photochemistry; visible light

Year:  2016        PMID: 27599166     DOI: 10.1002/chem.201604014

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


  5 in total

Review 1.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

Review 2.  Photoredox-Catalyzed C-H Functionalization Reactions.

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

3.  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

4.  Radical-mediated direct C-H amination of arenes with secondary amines.

Authors:  Sebastian C Cosgrove; John M C Plane; Stephen P Marsden
Journal:  Chem Sci       Date:  2018-07-11       Impact factor: 9.825

5.  Enantioselective catalytic β-amination through proton-coupled electron transfer followed by stereocontrolled radical-radical coupling.

Authors:  Zijun Zhou; Yanjun Li; Bowen Han; Lei Gong; Eric Meggers
Journal:  Chem Sci       Date:  2017-06-15       Impact factor: 9.825

  5 in total

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