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. 2022 Jun 3;12(11):6532-6549.
doi: 10.1021/acscatal.2c00318. Epub 2022 May 18.

Catalytic Oxidative Coupling of Phenols and Related Compounds

Jingze Wu  1 , Marisa C Kozlowski  1
Affiliations

Catalytic Oxidative Coupling of Phenols and Related Compounds

Jingze Wu et al. ACS Catal. .

Abstract

Phenols and their derivatives are the elementary building blocks for several classes of complex molecules that play essential roles in biological systems. Nature has devised methods to selectively couple phenolic compounds, and many efforts have been undertaken by chemists to mimic such coupling processes. A range of mechanisms can be involved and with well-studied catalysts, reaction outcomes in phenol-phenol oxidative coupling reactions can be predicted with a good level of fidelity. However, reactions with catalysts that have not been studied or that do not behave similarly to known catalysts can be hard to predict and control. This Perspective provides an overview of catalytic methods for the oxidative coupling of phenols, focusing on the last 10 years, and summarizes current challenges.

Keywords: biphenols; cross-coupling; dehydrogenative coupling; oxidative coupling; phenol coupling.

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1.
Scheme 1.
Retrosynthetic Analysis of Honokiol
Scheme 2.
Scheme 2.
Effect of Oxidation Potentials on Reaction Outcomes
Scheme 3.
Scheme 3.
Phenol-Phenol Coupling Site-selectivity
Scheme 4:
Scheme 4:
Enantioselective Phenol-Phenol Oxidative Coupling
Scheme 5:
Scheme 5:
Oxidative Phenol Coupling and Possible Reaction Outcomes
Scheme 6:
Scheme 6:
Intramolecular Phenol-Phenol Coupling and Myricanol Synthesis
Scheme 7:
Scheme 7:
Mechanisms of Oxidative Phenol Coupling Reaction
Scheme 8:
Scheme 8:
Resonance Forms of a Phenoxyl Radical
Scheme 9:
Scheme 9:
Selective Phenol Homo-Coupling Reactions.
Scheme 10:
Scheme 10:
Photocatalytic Phenol Homo-Coupling Reactions
Scheme 11:
Scheme 11:
a) ortho-para Site Selective Oxidative Phenol Homo-Coupling b) ortho-para Site Selective Oxidative Phenol Homo-Coupling Leading to Pummerer Ketone Generation
Scheme 12:
Scheme 12:
Hydroxycarbazole ortho-ortho’ Dimerization and ortho-ortho Tetramerization
Scheme 13:
Scheme 13:
Electrochemical meta-meta/meta-para Oxidative Phenol Couplings
Scheme 14:
Scheme 14:
Chromium Catalyzed Phenol Cross-Coupling
Scheme 15:
Scheme 15:
Electrochemical and Iron Catalyzed Phenol Cross-Coupling
Scheme 16:
Scheme 16:
Photocatalytic Phenol Cross-Coupling
Scheme 17:
Scheme 17:
Enantioselective Phenol-Phenol Oxidative Coupling
Scheme 18:
Scheme 18:
Enantioselective Phenol-Phenol Oxidative Coupling Mechanism
Scheme 19:
Scheme 19:
Ruthenium Catalyzed Enantioselective Cross-Coupling Reaction
Scheme 20:
Scheme 20:
Vanadium Catalyzed Enantioselective Cross-Coupling Reaction
Scheme 21:
Scheme 21:
Scope of the Intramolecular Oxidative Phenol Coupling with a Vanadium Catalyst
Scheme 22:
Scheme 22:
Natural Products with Phenol C–O Couplings
Scheme 23:
Scheme 23:
C–C/C–O/C–O Phenol Coupling with a Copper Catalyst
Scheme 24:
Scheme 24:
Mechanism of the C–C/C–O/C–O Phenol Coupling
Scheme 25:
Scheme 25:
Unsymmetrical Trimerization via C–O Coupling
Scheme 26:
Scheme 26:
Linear Triphenols from the ortho-Quinone Spiroketals
Scheme 27:
Scheme 27:
Naphthylamine Phenol C–C vs C–O coupling
Scheme 28:
Scheme 28:
Copper Catalyzed Selective Phenol C–O Coupling
Scheme 29:
Scheme 29:
β-O Alkenylphenol Coupling with a Vanadium Catalyst
Scheme 30:
Scheme 30:
Mechanism of Vandium Catalyzed β-O vs β-β Alkenylphenol Coupling
Scheme 31:
Scheme 31:
β-β Alkenylphenol Coupling with a Vanadium Catalyst
Scheme 32:
Scheme 32:
Exocyclic Oxidative Phenol Coupling Reaction
Scheme 33:
Scheme 33:
Aniline-Phenol/Aminonaphthalene-Phenol Oxidative Couplings
Scheme 34:
Scheme 34:
Aniline-Phenol/oxizole -Phenol Oxidative Couplings
Scheme 35:
Scheme 35:
β-Ketoesters/Phenols Oxidative Couplings
Scheme 36:
Scheme 36:
β-Ketoesters/Phenols Oxidative Couplings C–C vs C–O
Scheme 37:
Scheme 37:
Malononitriles-Phenol/Aniline/Heteroarene Oxidative Coupling
Scheme 38:
Scheme 38:
Phenol/Arene Oxidative Coupling with Fe Catalyst or Through Electrochemical Processes
Scheme 39:
Scheme 39:
Oxidative Coupling of Phenols and Alkenes
Scheme 40:
Scheme 40:
Oxidative Coupling of Phenols and Hydrazides
Scheme 41:
Scheme 41:
Copper Catalyzed Oxindole Oxidative Coupling Reactions
See this image and copyright information in PMC

References

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