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DOI: 10.1055/s-0034-1378674
Synthesis of Multiply Arylated Heteroarenes, Including Bioactive Derivatives, via Palladium-Catalyzed Direct C–H Arylation of Heteroarenes with (Pseudo)Aryl Halides or Aryliodonium Salts
Publication History
Received: 17 April 2014
Accepted after revision: 12 May 2014
Publication Date:
15 October 2014 (online)
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Abstract
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
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For examples of multiply arylated heteroarenes that are light-emitting liquid crystalline materials, see:
For reviews on the synthesis and biological properties of multiply arylated heteroarenes, see:
For examples of syntheses of multiply arylated heteroarenes via Suzuki-type cross-coupling reactions, see:
For examples of syntheses of multiply arylated heteroarenes via Stille-type cross-coupling reactions, see:
For examples of syntheses of multiply arylated heteroarenes via Pd-catalyzed Negishi reactions, see:
For leading references on Pd-catalyzed decarboxylative coupling reaction with (hetero)aryl halides, see:
For previous examples of Pd-catalyzed intermolecular C3 arylation reactions of 2-substituted benzo[b]furans with aryl halides, see:
For the synthesis of tetraarylthiophenes through Suzuki reactions between arylboronic acids and tetrabromothio-phene or 2,5-diaryl-3,4-dibromothiophenes, see:
For examples, see:
For previous examples of Pd-catalyzed direct intramolecular C3 arylation reactions of pyrroles, see:
For the synthesis of oxazoles from TosMIC and carbonyl compounds, see:
For additional examples of Pd-catalyzed direct C–H arylation reactions of (hetero)arenes on-water, see:
For previous syntheses of 2,4-diaryl-1H-1,2,3-triazoles, see:
For examples of 2,5-diaryl-1,3,4-thiazole derivatives with liquid crystal properties, see: