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Keywords = heterobiaryl compounds

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18 pages, 1698 KB  
Review
Enantioselective Iodination and Bromination for the Atroposelective Construction of Axially Chiral Compounds
by Xilong Wang, Shunwei Zhao, Yao Zhang, Dongya Bai, Fengbo Qu, Zhiyi Song, Hui Chen and Tingting Liu
Catalysts 2025, 15(7), 679; https://doi.org/10.3390/catal15070679 - 12 Jul 2025
Cited by 1 | Viewed by 909
Abstract
Axially chiral compounds play a pivotal role in organic synthesis, materials science, and pharmaceutical development. Among the various strategies for their construction, enantioselective iodination and bromination have emerged as powerful and versatile approaches, enabling the introduction of halogen functionalities that serve as valuable [...] Read more.
Axially chiral compounds play a pivotal role in organic synthesis, materials science, and pharmaceutical development. Among the various strategies for their construction, enantioselective iodination and bromination have emerged as powerful and versatile approaches, enabling the introduction of halogen functionalities that serve as valuable synthetic handles for further transformations. This review highlights recent advances in atroposelective iodination and bromination, with a particular focus on the synthesis of axially chiral biaryl and heterobiaryl frameworks. Key catalytic systems are discussed, including transition metal complexes, small-molecule organocatalysts, and high-valent metal catalysts in combination with chiral ligands or transient directing groups. Representative case studies are presented to elucidate mechanistic pathways, stereochemical induction models, and synthetic applications. Despite notable progress, challenges remain, such as expanding substrate scope, improving atom economy, and achieving high levels of regio- and stereocontrol in complex molecular settings. This review aims to provide a comprehensive overview of these halogenation strategies and offers insights to guide future research in the atroposelective synthesis of axially chiral molecules. Full article
(This article belongs to the Special Issue Asymmetric Catalysis: Recent Progress and Future Perspective)
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35 pages, 50152 KB  
Review
Asymmetric Synthesis of Axially Chiral Molecules via Organocatalytic Cycloaddition and Cyclization Reactions
by Wei-Yun Cai, Qian-Ni Ding, Ling Zhou and Jie Chen
Molecules 2023, 28(11), 4306; https://doi.org/10.3390/molecules28114306 - 24 May 2023
Cited by 6 | Viewed by 4228
Abstract
Atropisomeric molecules are present in many natural products, biologically active compounds, chiral ligands and catalysts. Many elegant methodologies have been developed to access axially chiral molecules. Among them, organocatalytic cycloaddition and cyclization have attracted much attention because they have been widely used in [...] Read more.
Atropisomeric molecules are present in many natural products, biologically active compounds, chiral ligands and catalysts. Many elegant methodologies have been developed to access axially chiral molecules. Among them, organocatalytic cycloaddition and cyclization have attracted much attention because they have been widely used in the asymmetric synthesis of biaryl/heterobiaryls atropisomers via construction of carbo- and hetero-cycles. This strategy has undoubtedly become and will continue to be a hot topic in the field of asymmetric synthesis and catalysis. This review aims to highlight the recent advancements in this field of atropisomer synthesis by using different organocatalysts in cycloaddition and cyclization strategies. The construction of each atropisomer, its possible mechanism, the role of catalysts, and its potential applications are illustrated. Full article
(This article belongs to the Special Issue Synthesis and Application of Atropisomeric Molecules)
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7 pages, 5449 KB  
Communication
Synthesis of New 2-Arylbenzo[b]furan Derivatives via Palladium-Catalyzed Suzuki Cross-Coupling Reactions in Aqueous Media
by Qianqian Chen, Panli Jiang, Mengping Guo and Jianxin Yang
Molecules 2018, 23(10), 2450; https://doi.org/10.3390/molecules23102450 - 25 Sep 2018
Cited by 9 | Viewed by 3889
Abstract
A series of novel benzofuran derivatives containing biaryl moiety were designed and synthesized by the Suzuki cross-coupling reactions. The reactions, performed in the presence of K2CO3, EtOH/H2O and Pd(II) complex as catalyst, gave the corresponding products in [...] Read more.
A series of novel benzofuran derivatives containing biaryl moiety were designed and synthesized by the Suzuki cross-coupling reactions. The reactions, performed in the presence of K2CO3, EtOH/H2O and Pd(II) complex as catalyst, gave the corresponding products in good to excellent yields. The methodology allows the facile production of heterobiaryl compounds, a unique architectural motif that is ubiquitous in medicinal chemistry. Full article
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22 pages, 5537 KB  
Article
Synthesis and Structure-Activity Relationship Analysis of 5-HT7 Receptor Antagonists: Piperazin-1-yl Substituted Unfused Heterobiaryls
by Lucjan Strekowski, Jarosław Sączewski, Elizabeth A. Raux, Nilmi T. Fernando, Jeff Klenc, Shirish Paranjpe, Aldona Raszkiewicz, Ava L. Blake, Adam J. Ehalt, Samuel Barnes, Timothy C. Baranowski, Shannon M. Sullivan, Grzegorz Satała and Andrzej J. Bojarski
Molecules 2016, 21(4), 433; https://doi.org/10.3390/molecules21040433 - 31 Mar 2016
Cited by 5 | Viewed by 8506
Abstract
A series of piperazin-1-yl substituted unfused heterobiaryls was synthesized as ligands of the 5-HT7 receptors. The goal of this project was to elucidate the structural features that affect the 5-HT7 binding affinity of this class of compounds represented by the model [...] Read more.
A series of piperazin-1-yl substituted unfused heterobiaryls was synthesized as ligands of the 5-HT7 receptors. The goal of this project was to elucidate the structural features that affect the 5-HT7 binding affinity of this class of compounds represented by the model ligand 4-(3-furyl)-2-(4-methylpiperazin-1-yl)pyrimidine (2). The SAR studies included systematical structural changes of the pyrimidine core moiety in 2 to quinazoline, pyridine and benzene, changes of the 3-furyl group to other heteroaryl substituents, the presence of various analogs of the 4-methylpiperazin-1-yl group, as well as additional substitutions at positions 5 and 6 of the pyrimidine. Substitution of position 6 of the pyrimidine in the model ligand with an alkyl group results in a substantial increase of the binding affinity (note a change in position numbers due to the nomenclature rules). It was also demonstrated that 4-(3-furyl) moiety is crucial for the 5-HT7 binding affinity of the substituted pyrimidines, although, the pyrimidine core can be replaced with a pyridine ring without a dramatic loss of the binding affinity. The selected ethylpyrimidine (12) and butylpyrimidine (13) analogs of high 5-HT7 binding affinity showed antagonistic properties in cAMP functional test and varied selectivity profile—compound 12 can be regarded as a dual 5-HT7/5-HT2AR ligand, and 13 as a multi-receptor (5-HT7, 5-HT2A, 5-HT6 and D2) agent. Full article
(This article belongs to the Section Medicinal Chemistry)
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14 pages, 267 KB  
Article
The Suzuki Reaction Applied to the Synthesis of Novel Pyrrolyl and Thiophenyl Indazoles
by Antonella Migliorini, Chiara Oliviero, Tecla Gasperi and Maria Antonietta Loreto
Molecules 2012, 17(4), 4508-4521; https://doi.org/10.3390/molecules17044508 - 16 Apr 2012
Cited by 21 | Viewed by 10767
Abstract
The paper describes the Suzuki cross-coupling of a variety of N and C-3 substituted 5-bromoindazoles with N-Boc-2-pyrrole and 2-thiopheneboronic acids. The reactions, performed in the presence of K2CO3, dimethoxyethane and Pd(dppf)Cl2 as catalyst, gave the corresponding [...] Read more.
The paper describes the Suzuki cross-coupling of a variety of N and C-3 substituted 5-bromoindazoles with N-Boc-2-pyrrole and 2-thiopheneboronic acids. The reactions, performed in the presence of K2CO3, dimethoxyethane and Pd(dppf)Cl2 as catalyst, gave the corresponding adducts in good yields. The methodology allows the facile production of indazole-based heteroaryl compounds, a unique architectural motif that is ubiquitous in biologically active molecules. Full article
(This article belongs to the Section Organic Chemistry)
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