Article
Chemistry, Organic
Mengna Liu, Benqiang Cui, Chuntao Zhong, Yanhui Shi, Yanfeng Dang, Changsheng Cao
Summary: A palladium-catalyzed cyanation of aryl dimethylsulfonium salts using K-4[Fe-(CN)(6)]center dot 3H(2)O as the cyanating reagent was successfully developed. The reaction proceeded under base-free conditions and yielded aryl nitriles with up to 92% yields. The protocol also allowed direct transformation of aryl sulfides to aryl nitriles, and the reaction mechanism was investigated using density functional theory calculations.
Article
Chemistry, Organic
Chongjiu Lu, Min Ye, Lipeng Long, Yue Zheng, Jiameng Liu, Yue Zhang, Zhengwang Chen
Summary: An efficient formal alkenyl C-H cyanation reaction has been developed for the synthesis of unsymmetrical diarylfumaronitriles. The advantages of this transformation include the use of a safe and non-toxic cyanide source, absence of external noble metal catalyst, easy availability of raw materials, good functional group tolerance, high stereoselectivity, and potential further application of the products.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Farzaneh Karimi, Masoumeh Jadidi Nejad, Arefe Salamatmanesh, Akbar Heydari
Summary: A highly efficient heterogeneous copper catalyst was developed by supporting copper acetate on a magnetically separable triazine-vitamin B-5 system. The prepared nanoparticles were characterized by various techniques and showed favorable catalytic efficiency in the cyanation reaction of aryl halides using nitromethane as a non-toxic and cost-effective cyanation source. The magnetic nanocatalyst could be easily recovered and reused multiple times without significant performance decrease.
Article
Chemistry, Multidisciplinary
A. Hess, H. C. Guelen, N. Alandini, A. Mourati, Y. C. Guersoy, P. Knochel
Summary: This study presents a novel method for the selective ortho, ortho'-functionalization of readily available aryl oxazolines using sBu(2)Mg in toluene followed by trapping reactions with electrophiles. The conversions of these nitriles to valuable heterocycles are reported, and a tentative mechanism is proposed for the reactions.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Lu Lei, Pei-Sen Zou, Zhi-Xin Wang, Cui Liang, Cheng Hou, Dong-Liang Mo
Summary: A regioselective Heck reaction catalyzed by a P-containing palladacycle was described, which affords 2-aryl-2,5-dihydrofurans and 2-aryl-2,3-dihydrofurans in good yields from 2,3-dihydrofuran with diaryliodonium salts and aryl iodides, respectively. Mechanistic studies and DFT calculations revealed the chemoselectivity and regioselectivity-determining step of this reaction.
Article
Chemistry, Multidisciplinary
Xiang Li, Gao-Wei Wang, Li-Xia Liu, Chang-Bin Yu, Yong-Gui Zhou
Summary: Here, the authors describe the first example of palladium-catalyzed asymmetric hydrogenolysis of easily accessible aryl triflates for the construction of axially chiral biaryl scaffolds. The resulting chiral biaryl compounds were used to prepare axially chiral monophosphine ligands, which were further employed in palladium-catalyzed asymmetric allylic alkylation with excellent enantioselectivities and high branched and linear ratios, highlighting the potential utility of this methodology.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Sha Peng, Luo Yang
Summary: A practical and convenient copper-catalyzed method for cyanation of aryl iodides using formamide as the cyano source has been developed. This method offers high yields of various aryl nitriles, and its lower reaction temperature and excellent substrate compatibility make it more attractive in synthetic and pharmaceutical chemistry.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xianqiang Kong, Yuchang Wang, Yiyi Chen, Xiaohui Chen, Long Lin, Zhong-Yan Cao
Summary: A practical and mild electrochemical protocol has been developed for cyanation and cyanomethylation of trimethylammonium salts through C-N bond cleavage without the need for external stoichiometric reducing agents or sacrificial anodes. The reaction shows high functional group compatibility and can be used for the synthesis of natural product derivatives. Preliminary mechanistic studies suggest the involvement of a radical addition pathway.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Yanan Hou, Hui Wang, Juan Xi, Ruonan Jiang, Lizhi Zhang, Xinjin Li, Fenggang Sun, Qing Liu, Zengdian Zhao, Hui Liu
Summary: Since the development of palladium-catalyzed cyanation in 1973, there has been widespread interest in the transition metal-catalyzed cyanation of aryl halides using Pd, Ni, and Cu. However, these reactions require highly polar organic solvents and high temperatures. In this study, we have developed a non-toxic K-4[Fe(CN)(6)]-promoted mechanochemical palladium-catalyzed solid-state cyanation of aryl bromides using an electromagnetic mill (EMM) without additional heating. This strategy offers a broad substrate scope, good functional group tolerance, liquid-assisted grinding, air and moisture insensitivity, no additional heating requirement, and efficient gram-scale synthesis.
Article
Chemistry, Organic
Kai Wang, Jiahua Wang, Wenkai Yuan, Xiang-Ying Tang, Long Wang
Summary: Divergent synthetic methods for converting isatins to 2-cyanoaryl carbamate and 2-cyanoaryl urea derivatives were developed, utilizing ammonium carbamate as the nitrogen source and iodobenzene diacetate as the oxidant. This reaction offers mild conditions, a wide range of substrate adaptability, and avoids the use of toxic cyano-containing compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Kai Wang, Jiahua Wang, Wenkai Yuan, Xiang-Ying Tang, Long Wang
Summary: Divergent synthetic methods were developed for transforming isatins to 2-cyanoaryl carbamate and 2-cyanoaryl urea derivatives, using ammonium carbamate as the nitrogen source and iodobenzene diacetate as the oxidant. This method features mild conditions, broad substrate scope, and the avoidance of toxic cyano-containing compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Pierre-Louis Lagueux-Tremblay, Celestin Augereau, Pranav Nair, Kwan Ming Tam, Bruce A. Arndtsen
Summary: The use of metal catalysis to form potent acylating agents is an important approach to expand the application of carbonylation reactions. However, the reductive elimination of these reactive products has been a challenge, making these reactions often high temperature, high pressure, and limited in scope. In this study, a mild and versatile palladium catalyzed carbonylative method was developed to generate electrophilic acyl-DMAP salts by exploiting the counterion. The weakly coordinating triflate anion was found to destabilize Pd(II) and enable irreversible reductive elimination, while ligand design facilitated the rapid activation of aryl or vinyl triflates. This approach allows palladium catalyzed carbonylations to be carried out under exceptionally mild conditions, with low catalyst loading and using readily available C(sp2)-triflate reagents.
Article
Chemistry, Organic
Si-Zhan Liu, Jing Li, Cao-Gen Xue, Xue-Tao Xu, Lin-Sheng Lei, Chen-Yu Huo, Zhen Wang, Shao-Hua Wang
Summary: A copper-promoted cyanation of aryl iodides has been developed using N,N-dimethyl aminomalononitrile as the cyanide source, with moderate toxicity and good stability. This method exhibits a broad substrate scope, excellent reaction yields, readily available catalyst, and simple reaction conditions.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Miao Wang, On Ying Yuen, Chau Ming So
Summary: This paper presents the first examples of palladium-catalyzed desulfinative cross-coupling reaction of polyhalogenated aryl triflates with aryl sulfinate salts. The catalyst system exhibited excellent reactivity and chemoselectivity in this reaction, which had a wide substrate scope and provided a simple method for constructing functionalized biaryl motifs. The interaction between the indolyl phosphine ligand and the Pd center played a key role in the reactivity and chemoselectivity of this reaction.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Physical
Pierre-Louis Lagueux-Tremblay, Celestin Augereau, Pranav Nair, Kwan Ming Tam, Bruce A. Arndtsen
Summary: The use of metal catalysis to form potent acylating agents is an important method to broaden the applicability of carbonylation reactions. However, the reductive elimination of these reactive products has presented a challenge, making the reactions often high temperature and high pressure, and limited in scope. In this study, a mild and versatile palladium catalyzed carbonylative method was developed to generate electrophilic acyl-DMAP salts. The use of triflate anion as a counterion destabilizes Pd(II) and allows for irreversible reductive elimination, while ligand design enables the rapid activation of aryl or vinyl triflates.
Article
Chemistry, Organic
Dilek Isik Tasgin, Irem Bayraktar
Summary: We present a synthetic method for pyrrolizine-3-one derivatives and investigate their photophysical properties. These compounds are prepared through a series of reactions involving substituted pyrroles in one-pot, two-step oxidation, and intramolecular cyclization processes. The photophysical properties of the synthesized compounds are studied using UV-Vis and fluorescence spectroscopy in various solvents. The introduction of pyrrolyl substituents has a significant impact on Stokes shifts and quantum yield values.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Satish Kumar Burra, Vaikunta Rao Lakinani, Raghunadh Akula, Chiranjeevi Yankkanti
Summary: A novel and green strategy for the construction of biologically relevant substituted indolyl-4H-chromenes scaffolds is reported, using L-proline as a catalyst and water as a promoter solvent. This catalytic system offers wider applicability, shorter reaction times, and high yields, making it an ideal condition for green chemistry.
SYNTHETIC COMMUNICATIONS
(2024)
Review
Chemistry, Organic
Abouelhaoul El Alami, Amine El Maraghi, Fatima Youssoufi, Assiya Atif, Hamid Sdassi
Summary: Nitrobenzimidazoles have become increasingly important in the design of new compounds in medicinal, therapeutic and chemical fields. This review provides an overview of the synthesis strategies and biological activities of nitrobenzimidazole derivatives.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Nilesh Raghunath Khedkar, Alex Joseph, Milind Sindkhedkar
Summary: In this study, a new library of 3-(2-(pyrimidin-5-yl)thiazol-4-yl)-1,2,4-oxadiazole compounds was designed and synthesized as potential anticancer agents using in silico fragment-based drug design. The compounds were tested for their anticancer activity in vitro, and one compound exhibited excellent activity against multiple cancer cell lines.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Terungwa H. Iorkula, Bryce A. Tolman, Scott R. Burt, Matt A. Peterson
Summary: A new method for synthesizing C-6 substituted products has been discovered in this study, which utilizes lower doses of fluoride and CsF as a catalyst, with high reaction yields and cost-effectiveness under suitable conditions.
SYNTHETIC COMMUNICATIONS
(2024)
Review
Chemistry, Organic
Ranjana Aggarwal, Swati Sharma
Summary: This review article mainly focuses on the synthesis of 3(5)-trifluoromethylpyrazoles via condensation reaction of trifluoromethyl-beta-diketones with hydrazines. It emphasizes the importance of fluorine-containing compounds and pyrazoles in the field of biology. The literature reported condensation reactions of trifluoromethyl-beta-diketones with hydrazines are covered.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
F. M. Alshareef, Sami A. Al-Harbi, Esam S. Allehyani, Omeima Abdullah, Magdy A. Ibrahim
Summary: This study aimed to construct a novel category of linear annulated chromeno[3',2':5,6]pyrido[2,3-d][1,3]thiazolo[3,2-a]pyrimidines. The chemical reactivity of the synthesized compounds was investigated, and they showed significant antimicrobial activity against various strains.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Preethi Dhanapal, S. L. Manju
Summary: Thiazole based Schiff base scaffolds have become an integral part of drug development in recent years, playing a versatile role as building blocks for lead drug molecules. This study presents a facile one pot synthetic method for producing novel 4-aryl thiazoles with high yield, shorter reaction time, and milder conditions, without the need for catalysts or purification techniques.
SYNTHETIC COMMUNICATIONS
(2024)