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Tetrasubstituted 1H-imidazoles are a large family of heteroarene derivatives that are known to include natural products isolated from marine sponges and synthetic compounds possessing a broad range of biological and pharmacological properties. Consequently, a great deal of attention has been given to the synthesis of these heteroarenes and reviews covering some synthetic aspects of this topic have been published in recent years. However, none of these reviews provides a comprehensive overview of the catalytic methods developed in the literature for the preparation of this important class of heteroarenes. This article aims to provide an updated critical picture of the catalytic processes reported in the literature up to the end of 2017 for the synthesis of 1,2,4,5-tetrasubstituted 1H-imidazoles illustrating these protocols and their characteristic features such as scope, efficiency, versatility, and limitations. The review also summarizes the mechanisms proposed for many of the reported processes. [ABSTRACT FROM AUTHOR]

Two methods for the one-pot synthesis of 2,5-diarylimidazoles by palladium-catalyzed direct C--H arylation of 1-substituted imidazoles with aryl bromides have been devised. The first method, promoted by copper(I) iodide, is best suited for electron-poor aryl bromides, and also allows the 2,5-diarylation of thiazole and oxazole. The use of xylene instead of DMA is the key for the efficiency of the second method, which gives the best results with electron-rich aryl bromides. [ABSTRACT FROM AUTHOR]

This review with 387 references covers the literature until the end of November 2013 on the synthesis of multiply arylated heteroarenes via highly selective palladium-catalyzed direct C-H arylation reactions of heteroarene derivatives with aryl halides or pseudohalides or aryliodonium salts. Particular attention has been made to describe the synthesis of biologically active compounds and substances that are privileged structural motifs in organic materials. The practicality, versatility, and limitations of the various developed arylation protocols are discussed. 1 Introduction 2 Synthesis of Multiply Arylated Five-Membered Hetero­arenes with One Heteroatom 2.1 Multiply Arylated Furan and Benzo[b]furan Derivatives 2.2 Multiply Arylated Thiophenes and Benzo[b]thiophene Derivatives 2.3 Multiply Arylated Pyrrole and Indole Derivatives 3 Synthesis of Multiply Arylated Five-Membered Hetero­arenes with Two or More Heteroatoms 3.1 Multiply Arylated Pyrazole and 2H-Indazole Derivatives 3.2 Multiply Arylated Isoxazole Derivatives 3.3 Multiply Arylated Oxazole Derivatives 3.4 Multiply Arylated Thiazole and Thiazole N-Oxide Derivatives 3.5 Multiply Arylated Imidazole and Imidazole N-Oxide Derivatives­ 3.6 Multiply Arylated 1,2,3-Triazole and 1,2,3-Triazole N-Oxide Derivatives 3.7 Diarylated 1,2,4-Triazole and 1,3,4-Thiadiazole Derivatives 3.8 Diarylated Sydnone, 2,1,3-Benzothiadiazole, and Tetrazole Derivatives 4 Synthesis of Multiply Arylated Six-Membered Hetero­arenes 4.1 Diarylated Pyridines, Pyridine N-Oxides, and Pyrazine N-Oxides 5 Synthesis of Multiply Arylated Compounds Formed by Five-Membered Heteroarenes Fused to Five-Membered Heteroarenes 5.1 Diarylated Thieno[2,3-b]thiophenes, Imidazo[1,2-b]pyrazoles, and Thiazolo[3,2-b]-1,2,4-triazoles 6 Synthesis of Multiply Arylated Compounds Formed by Six-Membered Heteroarenes Fused to Five-Membered Hetero­arenes 6.1 Diarylated Indolizines, Pyrimido[5,4-b]indolizines, Pyrrolo[2,3-b]pyridines, Pyrazolo[1,5-a]pyrimidines, Imidazo[1,2-a]pyridines, Imidazo[1,5-a]pyridines, Xanthines, Imidazo[1,2-b]tetrazines, Imidazo[1,2-a]pyrazines, and ­Furo[3,2-b]pyridines 7 Conclusions [ABSTRACT FROM AUTHOR]

Review: [175 refs. [ABSTRACT FROM AUTHOR]

The article presents chemical equations related to the article "Highly Regioselective C-5 Alkynylation of Imidazoles by One-Pot Sequential Bromination and Sonogashira Cross Coupling" by F. Bellina and others, published in the periodical "Tetrahedron Letters" in 2015.

Review: results obtained from January 2009 to February 2013 in the area of transition metal-catalyzed title arylation reactions; 430 refs. [ABSTRACT FROM AUTHOR]

Abstract: A new insoluble polymer-bound bisoxazoline (IPB-box) was prepared by grafting a suitable chiral ligand derivative onto a commercial Merrifield resin. The material obtained by this route was employed in the asymmetric copper-catalyzed olefin cyclopropanation, obtaining good activity and enantioselectivity values (54–84% yield, 71–93% ee) for a range of substrates. In addition, some key factors required for the development of effective IPB-box systems are discussed, including the local ligand symmetry and the influence of immobilization technique and catalyst loading. [Copyright &y& Elsevier]