Article
Chemistry, Multidisciplinary
Shiyao Liu, Yoshiaki Tanabe, Shogo Kuriyama, Ken Sakata, Yoshiaki Nishibayashi
Summary: In recent years, significant progress has been made in the development of transition metal-catalyzed enantioselective propargylic substitution reactions. However, until now, no successful example with phosphorus-centered nucleophiles has been reported. This study presents the first successful example of ruthenium-catalyzed enantioselective propargylic substitution reactions using propargylic alcohols as substrates and diarylphosphine oxides as phosphorus-centered nucleophiles, providing a new method for preparing chiral phosphorus-containing organic compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Zhiheng Li, Danran Li, Huaming Xiang, Jian Huang, Yinuo Zheng, Cuiju Zhu, Xiuling Cui, Chao Pi, Hao Xu
Summary: In this study, a highly enantioselective propargylic substitution reaction of anthrones with propargylic esters using copper salts with chiral N, N, P-ligand was disclosed. This strategy shows broad substrate compatibility, mild reaction conditions, excellent yields with remarkable enantioselectivity, and enables the synthesis of diverse products.
CHINESE CHEMICAL LETTERS
(2022)
Editorial Material
Chemistry, Multidisciplinary
Shiyao Liu, Yoshiaki Tanabe, Shogo Kuriyama, Ken Sakata, Yoshiaki Nishibayashi
Summary: The cover of this issue features the research on the propargylic substitution reaction of propargylic alcohol with an N-monosubstituted hydrazone, where the nucleophilicity of the hydrazone is controlled by the choice of catalytic system. The full article can be accessed at 10.1002/chem.202103287.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Shiyao Liu, Yoshiaki Tanabe, Shogo Kuriyama, Ken Sakata, Yoshiaki Nishibayashi
Summary: In this study, propargylic substitution reactions using ruthenium and copper catalysis with N-monosubstituted hydrazones as ambident nucleophiles were investigated. It was found that N-monosubstituted hydrazones exhibited different reactivities depending on the catalytic system, resulting in either propargylic alkylated or aminated products. DFT calculations were used to study the reaction pathways and further transformation of the products yielded multisubstituted pyrazoles in good to high yields.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Xiangrong Liu, Xue Tian, Jiawu Huang, Yu Qian, Xinfang Xu, Zhenghui Kang, Wenhao Hu
Summary: An enantioselective three-component reaction of alpha-propargylic-3-indolymethanol with diazoindolinone and alcohol has been achieved under the cocatalysis of Rh(II) and chiral phosphoric acid (CPA). The reaction proceeds through regio- and enantiospecific addition of an in situ formed oxonium ylide to the alpha-propargylic indole iminium ion, providing an efficient access to chiral propargylic indole derivatives with high yields and enantioselectivities.
Article
Multidisciplinary Sciences
Xihao Chang, Jiayin Zhang, Lingzi Peng, Chang Guo
Summary: The study introduces an enantioselective nickel/Lewis acid-catalyzed asymmetric propargylic substitution reaction for the synthesis of structurally diverse natural products from simple achiral materials under mild conditions. The addition of a Lewis acid cocatalyst is crucial for enhancing the efficiency of the transformation and the strategy is powerful for collectively synthesizing seven biologically active compounds.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Inorganic & Nuclear
Pol de la Cruz-Sanchez, Maria Biosca, Marc Magre, Jorge Faiges, Jessica Margalef, Oscar Pamies, Montserrat Dieguez
Summary: High enantioselectivities and activities were achieved in the Pd-catalyzed allylic substitution reaction using a family of adaptable ligands. The ligands demonstrated high performance in various catalytic processes.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dandan Sun, Thayalan Rajeshkumar, Yifan Li, Jiaxin Xu, Runkai Chen, Zhaohua Wan, Zongchao Lv, Laurent Maron, Yi-Hung Chen
Summary: Transition-metal-catalyzed cross-coupling of propargylic electrophiles and Grignard reagents provides useful synthetic intermediates. However, few examples exist for the conversion of propargylic derivatives into propargyl compounds due to the challenging regioselectivity. We demonstrate a regioselective and stereospecific propargylation of Grignard reagents using LaCl3.2LiCl as a catalyst in the absence of a ligand.
Article
Chemistry, Physical
Suman Sar, Prasanta Ghorai
Summary: Here, we have developed an efficient intramolecular umpolung chemodivergent cascade route for synthesizing 1-indanones by precisely controlling the umpolung reactivity between the α-diketone and π-allyl Pd complex. This strategy combines the advantages of chemodivergent and umpolung strategies, resulting in a broad array of 1-indanones with high yield and selectivity. The significance of this protocol is further amplified by the successful scale-up synthesis and post-synthetic transformations. Additionally, we have efficiently achieved diastereomers of ether and alcohol derivatives of 1-indanone through synthetic transformations.
Article
Chemistry, Organic
Han Yang, Zhen Chen, Wenjing Guo, Zhenhua Gu
Summary: A palladium-catalyzed cross-coupling reaction between 3-iodoazetidines and nonheteroaryl boronic acids was reported in this study. The reaction was facilitated by the [1,1'-biphenyl]-2-yldicyclohexylphosphane ligand, leading to the formation of 2-aryl azetidines. Control experiments indicated that the reaction can proceed through either a palladiumhydride/dihydroazete complex or free dihydroazete intermediate followed by hydropalladation.
Article
Chemistry, Organic
Haoran Zhao, Anju Treesa Jose, Alisajat Asany, Shahrukh M. Khan, Mark R. Biscoe
Summary: A general process for the formation of alpha-arylethers via Pd-catalyzed arylation has been developed. This process achieves selective alkyl transfer by incorporating cyclo-hexyl spectator ligands and using the electron-deficient ligand JackiePhos (1), eliminating the need for coordinating/directing oxygen-protecting groups.
Article
Chemistry, Organic
Wen-Ya Lu, Yong You, Ting-Ting Li, Zhen-Hua Wang, Jian-Qiang Zhao, Wei-Cheng Yuan
Summary: A new method for synthesizing allenyl thioether compounds via CuI-catalyzed decarboxylative thiolation of terminal alkyne-substituted cyclic carbonates/carbamates has been successfully developed. A variety of hydroxymethyl- and aminomethyl-containing allenyl thioethers were obtained in good to excellent yields under mild conditions. The copper-allenylidene intermediate plays a crucial role in the decarboxylative thiolation reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Prashant Kumar, Mrudula M. Nikam, S. S. V. Ramasastry
Summary: In this study, we described the first palladium-catalyzed cascade annulative allylic alkylation of benzylic gem-diacetates to access complex analogues of (hetero)arene-fused benzo[f]chromenes, which have relevance in medicinal chemistry and materials science.
Article
Chemistry, Organic
Pablo Macias-Benitez, Alfonso Sierra-Padilla, Manuel J. Tenorio, F. Javier Moreno-Dorado, Francisco M. Guerra
Summary: The study utilized microwave irradiation to promote the oxyphosphorylation of alkynes with diethyl phosphite and t-butyl hydroperoxide in the presence of [Cu(MeCN)(4)]BF4, yielding different phosphonylated indenones.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jie Xu, Zhaoliang Ge, Kuiling Ding, Xiaoming Wang
Summary: Regio-divergent propargylic substitution has been a challenging problem due to the unpredictable regiochemical complexity. In this study, a three-component propargylic substitution of a-diazo esters with amines and propargylic carbonates was achieved through a tandem reaction of dual catalysis.
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)
