4.8 Article

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

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 36, Pages 10872-10876

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201605865

Keywords

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

Funding

  1. DFG [Wa1278/14-1]
  2. Max Planck Graduate Center

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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.

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