Literature DB >> 27532512

Metal-free C-H sulfonamidation of pyrroles by visible light photoredox catalysis.

Andreas Uwe Meyer1, Anna Lucia Berger, Burkhard König.   

Abstract

We report a one-step procedure for the preparation of N-(2-pyrrole)-sulfonamides from sulfonamides and pyrroles. The reaction uses visible light, an acridinium dye as photocatalyst and oxygen as the terminal oxidant for the oxidative C-N bond formation; structures of several reaction products were confirmed by X-ray structure analysis. The reaction is selective for pyrroles, due to the available oxidation power of the photocatalyst and the required stability of the carbocation intermediate under the reaction conditions.

Entities:  

Year:  2016        PMID: 27532512     DOI: 10.1039/c6cc06111g

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


  4 in total

Review 1.  Photoredox-Catalyzed C-H Functionalization Reactions.

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

2.  Direct sulfonylation of anilines mediated by visible light.

Authors:  Tarn C Johnson; Bryony L Elbert; Alistair J M Farley; Timothy W Gorman; Christophe Genicot; Bénédicte Lallemand; Patrick Pasau; Jakub Flasz; José L Castro; Malcolm MacCoss; Darren J Dixon; Robert S Paton; Christopher J Schofield; Martin D Smith; Michael C Willis
Journal:  Chem Sci       Date:  2017-11-16       Impact factor: 9.825

3.  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

Review 4.  Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry.

Authors:  Michael K Bogdos; Emmanuel Pinard; John A Murphy
Journal:  Beilstein J Org Chem       Date:  2018-08-03       Impact factor: 2.883

  4 in total

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