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Synthesis 2016; 48(22): 3821-3862
DOI: 10.1055/s-0036-1588303
DOI: 10.1055/s-0036-1588303
review
Direct (Hetero)arylation Reactions of (Hetero)arenes as Tools for the Step- and Atom-Economical Synthesis of Biologically Active Unnatural Compounds Including Pharmaceutical Targets
Further Information
Publication History
Received: 18 May 2016
Accepted after revision: 16 June 2016
Publication Date:
11 October 2016 (online)
Abstract
The significant number of papers and reviews published in this last decade testifies to the utility of the transition-metal-catalyzed direct C–H (hetero)arylation reactions of (hetero)arenes as efficient and powerful tools for the step- and atom-economical, regio- and chemoselective synthesis of natural and unnatural compounds. However, no review has so far been devoted to summarizing the application of these reactions in the synthesis of biologically active compounds. This review with 341 references aims to fill this gap, providing a comprehensive picture of the transition-metal-catalyzed intra- and intermolecular direct C–H (hetero)arylation reactions of (hetero)arenes with (hetero)aryl halides or pseudohalides that have been used as key steps of syntheses of unnatural biologically relevant compounds including pharmaceutical targets, up to the end of September 2015. Attention has also been directed to provide a brief description of the biological properties of the synthesized compounds.
1 Introduction
2 Syntheses via Intramolecular Direct (Hetero)arylation of (Hetero)arene Derivatives
3 Syntheses via Intermolecular Direct (Hetero)arylation Reactions
3.1 Of Arenes
3.2 Of Five-Membered Heteroarenes with One Heteroatom
3.3 Of Five-Membered Heteroarenes with Two Heteroatoms
3.4 Of Five-Membered Heteroarenes with Three and Four Heteroatoms
3.5 Of Five-Membered Heteroarenes Fused to a Six-Membered Heteroarene
3.6 Of Five-Membered Heteroarene Moieties of Tricyclic Heteroarenes
3.7 Of Six-Membered Heteroarenes
4 Syntheses of Nitrogen-Containing Polycyclic Heteroarene via One-Pot Palladium-Catalyzed Domino Direct Arylation/N-Arylation Reactions
5 Conclusions
-
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For additional papers on nitrogen-directed ortho-arylation reactions catalyzed by ruthenium derivatives, see:
For additional papers on Co-catalyzed direct arylation reactions, see:
For leading references on the synthesis of biaryls via palladium-catalyzed decarboxylative coupling reactions, see:
For additional references on the direct regioselective arylation of nitro(hetero)arene derivatives, see:
For additional syntheses of Boscalid®, see:
For literature data on the palladium-catalyzed direct C-5 arylation reactions of 2-substituted furans, see:
For previous examples of palladium-catalyzed highly selective β-arylation reactions of thiophenes with iodoarenes in the presence of P[OCH(CF3)2]3 ligand, see:
For additional examples of palladium-catalyzed ligand-free direct arylation reactions involving the use of n-Bu4NBr as an additive, see:
For additional examples of palladium-catalyzed regioselective intermolecular direct C5-arylation reactions of 1-substituted pyrazole derivatives, see:
For additional syntheses of Celecoxib, see:
For additional examples of palladium-catalyzed direct C3-arylation of 1H-indazoles, see:
For additional examples of transition-metal-catalyzed direct (hetero)arylation reactions in which water was used as solvent, see:
For selected reviews on chloroquine, see:
For additional examples of ligand-free palladium-catalyzed direct C5-arylation reactions of thiazole derivatives, see:
For protocols on the palladium-catalyzed direct C5-arylation of imidazole derivatives that have been developed by research groups other than ours, see:
For palladium-catalyzed direct C2-arylation reactions of 1-substituted imidazoles that have been reported by research groups other than ours, see:
For additional examples of syntheses of 1,2,3-triazole derivatives via CuSO4/sodium ascorbate catalyzed click reactions, see:
For directed ortho-arylation of benzamides in an acidic solvent, see:
For recent examples of direct arylation reaction which have been carried out using a low catalyst loading, see ref. 60d and:
For recent examples of direct arylation reactions carried out using new catalyst systems, see ref. 127c and:
For typical examples, see: