Efficient Microwave Method for the Oxidative Coupling of Phenols

GRAPHICAL ABSTRACT Abstract: The tert-butyl peroxide–initiated, oxidative coupling of phenols can frequently promote reactions that otherwise perform poorly under alternative conditions. Despite this utility, peroxide coupling reactions employing conventional heat often require high-dilution conditions, multiple additions of oxidant, and long reflux times, while regularly affording only moderate product yields. We recently developed an optimized protocol for peroxide-promoted, oxidative coupling that employs microwave heat. Product yields up to 98% have been attained. The performance and scope of this method relative to other oxidative coupling methodologies will be discussed.

[1]  C. M. Lawson,et al.  Synthesis, linear and nonlinear optical properties of phosphonato-substituted bithiophenes derived from 2,2'-biphenol. , 2013, Dalton transactions.

[2]  A. Chaudhary,et al.  Honokiol analogs: a novel class of anticancer agents targeting cell signaling pathways and other bioactivities. , 2013, Future medicinal chemistry.

[3]  M. Tian,et al.  Cobalt(II)–Porphyrin‐Catalyzed Aerobic Oxidation: Oxidative Coupling of Phenols , 2013 .

[4]  Arnaud Nourry,et al.  Evidence for a trianion intermediate in the metalation of 4-hydroxy-6,7-dimethoxy-8-methyl-2-naphthoic acid. Methodology and application to racemic 5,5'-didesisopropyl-5,5'-dialkylapogossypol derivatives. , 2011, The Journal of organic chemistry.

[5]  Hui Wang.  Recent advances in asymmetric oxidative coupling of 2-naphthol and its derivatives. , 2010, Chirality.

[6]  Victoria L. Sun,et al.  Electron‐Withdrawing, Biphenyl‐2,2′‐diol‐Based Compounds for Asymmetric Catalysis , 2010 .

[7]  P. Wallis,et al.  Oxidative coupling revisited: solvent-free, heterogeneous and in water , 2006 .

[8]  A J Paine,et al.  Mechanisms of chromium toxicity, carcinogenicity and allergenicity: Review of the literature from 1985 to 2000 , 2001, Human & experimental toxicology.

[9]  R. S. Coleman,et al.  Synthesis of the spirocyclic cyclohexadienone ring system of the schiarisanrins. , 2000, Organic letters.

[10]  B. Lipshutz,et al.  A modular approach to nonracemic cyclo-BINOLs. Preparation of symmetrically & unsymmetrically substituted ligands , 1998 .

[11]  P. Laszlo,et al.  Catalysis of Friedel‐Crafts Alkylation by a Montmorillonite Doped with Transition‐Metal Cations , 1987 .

[12]  Colin G. Cameron,et al.  Oxidative coupling of phenols. Part 6. A study of the role of spin density factors on the product composition in the oxidations of 3,5-dimethylphenol and phenol , 1983 .

[13]  H. Wynberg,et al.  Asymmetric Phenol Oxidation. Stereospecific and Stereoselective Oxidative Coupling of a Chiral Tetrahydronaphthol , 1981 .