Literature DB >> 27490451

Synthesis of meta-Terphenyl-2,2''-diols by Anodic C-C Cross-Coupling Reactions.

Sebastian Lips1, Anton Wiebe1,2, Bernd Elsler1, Dieter Schollmeyer1, Katrin M Dyballa3, Robert Franke3,4, Siegfried R Waldvogel5,6.   

Abstract

The anodic C-C cross-coupling reaction is a versatile synthetic approach to symmetric and non-symmetric biphenols and arylated phenols. We herein present a metal-free electrosynthetic method that provides access to symmetric and non-symmetric meta-terphenyl-2,2''-diols in good yields and high selectivity. Symmetric derivatives can be obtained by direct electrolysis in an undivided cell. The synthesis of non-symmetric meta-terphenyl-2,2''-diols required two electrochemical steps. The reactions are easy to conduct and scalable. The method also features a broad substrate scope, and a large variety of functional groups are tolerated. The target molecules may serve as [OCO](3-) pincer ligands.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C coupling; electrochemistry; meta-terphenyl compounds; pincer ligands; protecting groups

Year:  2016        PMID: 27490451     DOI: 10.1002/anie.201605865

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  18 in total

1.  Silicon-Tethered Strategies for C-H Functionalization Reactions.

Authors:  Marvin Parasram; Vladimir Gevorgyan
Journal:  Acc Chem Res       Date:  2017-08-03       Impact factor: 22.384

2.  Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

Authors:  Xiaowei Wu; Takayuki Iwata; Adam Scharf; Tian Qin; Kyle D Reichl; John A Porco
Journal:  J Am Chem Soc       Date:  2018-04-25       Impact factor: 15.419

3.  Palladium-Catalyzed C-H Bond Acetoxylation via Electrochemical Oxidation.

Authors:  Anuska Shrestha; Melissa Lee; Anna L Dunn; Melanie S Sanford
Journal:  Org Lett       Date:  2017-12-22       Impact factor: 6.005

4.  Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance.

Authors:  Ming Yan; Yu Kawamata; Phil S Baran
Journal:  Chem Rev       Date:  2017-10-09       Impact factor: 60.622

Review 5.  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

6.  Electrochemical synthesis of N,N'-disubstituted indazolin-3-ones via an intramolecular anodic dehydrogenative N-N coupling reaction.

Authors:  Jessica C Bieniek; Michele Grünewald; Johannes Winter; Dieter Schollmeyer; Siegfried R Waldvogel
Journal:  Chem Sci       Date:  2022-06-13       Impact factor: 9.969

Review 7.  Electrifying Organic Synthesis.

Authors:  Anton Wiebe; Tile Gieshoff; Sabine Möhle; Eduardo Rodrigo; Michael Zirbes; Siegfried R Waldvogel
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-07       Impact factor: 15.336

8.  The Strong β-CF3 Shielding Effect in Hexafluoroisopropanol and 100 Other Organic Solvents Revisited with 17O NMR Spectroscopy.

Authors:  Annika Bernhardt; Harald Kelm; Frederic W Patureau
Journal:  ChemCatChem       Date:  2018-02-23       Impact factor: 5.686

9.  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

10.  Unexpected high robustness of electrochemical cross-coupling for a broad range of current density.

Authors:  Anton Wiebe; Barbara Riehl; Sebastian Lips; Robert Franke; Siegfried R Waldvogel
Journal:  Sci Adv       Date:  2017-10-06       Impact factor: 14.136

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