Literature DB >> 29493824

Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Benzofurans leading to a Furan Metathesis.

Sebastian Lips1, Bernardo Antonio Frontana-Uribe1,2, Maurice Dörr1, Dieter Schollmeyer1, Robert Franke3,4, Siegfried R Waldvogel1.   

Abstract

Heterobiaryls consisting of a phenol and a benzofuran motif are of significant importance for pharmaceutical applications. An attractive sustainable, metal- and reagent-free, electrosynthetic, and highly efficient method, that allows access to (2-hydroxyphenyl)benzofurans is presented. Upon the electrochemical dehydrogenative C-C cross-coupling reaction, a metathesis of the benzo moiety at the benzofuran occurs. This gives rise to a substitution pattern at the hydroxyphenyl moiety which would not be compatible by a direct coupling process. The single-step protocol is easy to conduct in an undivided electrolysis cell, therefore scalable, and inherently safe.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C coupling; electrochemistry; furan; heterocycles; oxidation

Year:  2018        PMID: 29493824     DOI: 10.1002/chem.201800919

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


  6 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

2.  Selective and Scalable Electrosynthesis of 2H-2-(Aryl)-benzo[d]-1,2,3-triazoles and Their N-Oxides by Using Leaded Bronze Cathodes.

Authors:  Tom Wirtanen; Eduardo Rodrigo; Siegfried R Waldvogel
Journal:  Chemistry       Date:  2020-03-30       Impact factor: 5.236

3.  About the selectivity and reactivity of active nickel electrodes in C-C coupling reactions.

Authors:  Sebastian B Beil; Manuel Breiner; Lara Schulz; Aaron Schüll; Timo Müller; Dieter Schollmeyer; Alexander Bomm; Michael Holtkamp; Uwe Karst; Wolfgang Schade; Siegfried R Waldvogel
Journal:  RSC Adv       Date:  2020-04-08       Impact factor: 3.361

4.  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

5.  Electrochemical Synthesis of Fluorinated Orthoesters from 1,3-Benzodioxoles.

Authors:  Johannes L Röckl; Adrian V Hauck; Dieter Schollmeyer; Siegfried R Waldvogel
Journal:  ChemistryOpen       Date:  2019-05-14       Impact factor: 2.911

6.  Dehydrogenative Anodic C-C Coupling of Phenols Bearing Electron-Withdrawing Groups.

Authors:  Johannes L Röckl; Dieter Schollmeyer; Robert Franke; Siegfried R Waldvogel
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-19       Impact factor: 15.336

  6 in total

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