Article
Chemistry, Inorganic & Nuclear
Nadia Ismaeel, Zhixing Zhuo, Sajid Imran, Dan Yuan, Yingming Yao
Summary: Rare earth/lithium complexes stabilized by ethylenediamine-bridged bis(phenolate) ligands have been synthesized and characterized. Among them, the yttrium/lithium complex showed high catalytic activity for the amidation of primary aliphatic amines.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Arun K. Ghosh, Dana Shahabi
Summary: The study presents a convenient protocol for amide bond formation, suitable for electron deficient amines and carboxylic acids, enabling the synthesis of a variety of functionalized amide derivatives.
TETRAHEDRON LETTERS
(2021)
Article
Multidisciplinary Sciences
Yu Guo, Ruo-Ya Wang, Jia-Xin Kang, Yan-Na Ma, Cong-Qiao Xu, Jun Li, Xuenian Chen
Summary: Amides, important organic compounds widely used in medicine, biochemistry, and materials science, can be efficiently synthesized through a direct amidation of esters with sodium amidoboranes without the need for catalysts. This method is rapid, chemoselective, and features wide applicability for esters tolerating different functional groups.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Harjeet S. Soor, Diego B. Diaz, Ka Yi Tsui, Karina Calvopina, Marcin Bielinski, Dean J. Tantillo, Christopher J. Schofield, Andrei K. Yudin
Summary: Amidoboronic acid-containing peptidomimetics, a crucial scaffold in chemistry and drug discovery, have been synthesized using a new methodology to prepare constrained alpha- and beta-amidoboronic acids. Quantum chemical calculations have revealed rate-limiting steps for different ring sizes, and a potential application of beta-amidoboronic acid derivatives as novel VIM-2 metallo-beta-lactamase inhibitors has been demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Karthick Govindan, Nian-Qi Chen, Alageswaran Jayaram, Wei-Yu Lin
Summary: We have developed an efficient method for synthesizing secondary amides using easily accessible N-(2-aminophenyl)benzamide and phenyl isocyanate. The leaving group can be conveniently recuperated as a carbonylated N-heterocycle, which is highly relevant in pharmaceutical applications. The key steps of this strategy involve a sequential nucleophilic/intramolecular addition process of phenyl isocyanate, followed by transamidation. Furthermore, this protocol offers atom-economy, practicality, a one-pot two-step reaction, and facile preparation of substrates.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Jin Zhang, Pei Zhang, Yangmin Ma, Michal Szostak
Summary: This study reports a novel solvent-free method for synthesizing ketones with high selectivity from acyl chlorides and boronic acids. The reaction takes place in the solid state, without the use of solvents, and has a short reaction time, demonstrating excellent selectivity for C(acyl)-Cl bond cleavage.
Article
Chemistry, Physical
Rabindranath Lo, Martin Pykal, Andreas Schneemann, Radek Zboril, Roland A. Fischer, Kolleboyina Jayaramulu, Michal Otyepka
Summary: Covalent hybrids of graphene and metal-organic frameworks (MOFs) have great potential in various technologies, especially catalysis and energy applications, due to their combination of conductivity and porosity. The formation of an amide bond between carboxylate-functionalized graphene acid (GA) and amine-functionalized UiO-66-NH2 MOF is an efficient strategy for creating such hybrids. This study used density functional theory (DFT) calculations to elucidate the mechanism of amide bond formation between GA and UiO-66-NH2, highlighting the crucial role of zirconium within UiO-66 as a catalyst. Insight into the binding interactions between graphene derivatives and MOFs can lead to tailored synthesis strategies for these nanocomposite materials.
JOURNAL OF PHYSICAL CHEMISTRY C
(2023)
Article
Chemistry, Organic
Christopher R. Opie, Hidetoshi Noda, Masakatsu Shibasaki, Naoya Kumagai
Summary: This Letter describes the design, synthesis, and evaluation of the first isolable N(BOH)2 compound as an amidation catalyst. The new catalyst outperforms the previously reported B3NO2 heterocycle catalyst, with respect to turnover frequency, albeit the former gradually decomposes upon exposure to amines. This work opens up an avenue for designing a better catalyst for direct amidation.
Article
Chemistry, Organic
Jessica M. L. Elwood, Martyr C. Henry, J. Daniel Lopez-Fernandez, Jenna M. Mowat, Mhairi Boyle, Benjamin Buist, Keith Livingstone, Craig Jamieson
Summary: We have reported the use of N-2,4-dinitrophenyltetrazoles as latent active esters (LAEs) in the synthesis of amide bonds. This method allows the generation of an HOBt-type active ester without the need for exogenous coupling agents. The methodology is applicable to a wide range of substrates, providing quantitative yields. The versatility and functional group tolerance were demonstrated in the one-step synthesis of various pharmaceutical agents and the N-acylation of resin-bound peptides.
Article
Biochemistry & Molecular Biology
Martin Kellert, Jan-Simon Jeshua Friedrichs, Nadine Anke Ullrich, Alexander Feinhals, Jonas Tepper, Peter Loennecke, Evamarie Hey-Hawkins
Summary: The development of novel boron-rich compounds for use in boron neutron capture therapy (BNCT) is an important field in cancer treatment. The study reports the design and synthesis of two promising compounds that combine meta-carborane, a water-soluble monosaccharide, and a linking unit for coupling with tumor-selective biomolecules. This approach enables the development of readily obtainable boron-rich agents with optimized properties for potential applications in BNCT.
Article
Chemistry, Inorganic & Nuclear
Isabel Abanades Lazaro, Ross S. Forgan, Francisco. G. Cirujano
Summary: The influence of composition and textural characteristics of ultra-small isoreticular UiO-type metal-organic frameworks (MOFs) on catalytic performance is evaluated in this study. The activity of Zr-MOF nanoparticles is tested using two different amide bond formation reactions as proof-of-concept. The results provide insights into the catalytic mechanism and optimal properties for enhancing performance.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Meixia Liu, Huimin Hu, Runbo Sun, Haoyuan Li, Anjun Ding, Xiaoyong Liu, Zhengjiang Fu, Shengmei Guo, Hu Cai
Summary: We present a nickel-catalyzed reductive cross-coupling method to synthesize phosphinic amides from readily available nitroarenes and phosphine oxides. The reaction employs NiCl2/Xantphos as catalyst, zinc as reductant, and TMSCl as additive, delivering various phosphinic amides in moderate to good yields. Notably, a gram-scale synthesis was successfully achieved, making this method practical for the synthesis of phosphinic amides. Mechanistic insights were also obtained from control experiments.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Qingyao Li, Peng Dai, Haidi Tang, Muliang Zhang, Jie Wu
Summary: The significance of amide functional groups in organic synthesis and pharmaceutical studies is widely recognized. However, current synthesis methods often involve the use of stoichiometric activating reagents and metallic reductants, leading to the production of toxic chemical waste. In this study, a photo-mediated hydrogen atom transfer catalysis is developed for direct reductive amidation reaction, which avoids the use of metallic reductants and toxic chemical waste. The method provides an efficient and practical strategy for the synthesis of amides.
Article
Chemistry, Multidisciplinary
Azat M. Gabdullin, Rita N. Kadikova, Oleg S. Mozgovoj, Ilfir R. Ramazanov
Summary: Under the catalysis of 0.2 equiv. TaCl5, alkyl- and aryl-substituted carboxylic acids react with primary and secondary amines to selectively form carboxylic acid amides of various structures. The TaCl5-catalyzed amide formation reaction proceeds with equal selectivity in toluene and methylene chloride, hexane, diethyl ether, and 1,4-dioxane solutions.
Article
Chemistry, Multidisciplinary
Shyamali Maji, Monojit Roy, Kanchan Shaikh, Debashis Adhikari
Summary: In this study, a new oxidation methodology using a cofactor-inspired approach is described. The photocatalytic reaction of pyrenedione under aerobic conditions enables the synthesis of amides from alcohols and amines via dehydrogenative intermolecular coupling. The reaction proceeds at room temperature and shows excellent synthetic utility with various substrates.
Article
Chemistry, Organic
Xinyang Gan, Shaofeng Wu, Furong Geng, Jianyu Dong, Yongbo Zhou
Summary: A metal-and oxidant-free photocatalytic C-H alkylation of coumarins was developed using triphenylphosphine and sodium iodide in the presence of blue LEDs irradiation. Easily available alkyl N-hydroxyphthalimide esters were used as the alkylation reagents. The protocol achieved various 3-alkylated coumarins and quinoxalinones with excellent C-3 regioselectivity.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Shaofeng Wu, Furong Geng, Jianyu Dong, Long Liu, Yongbo Zhou
Summary: A metal-free and highly general synthesis of benzoxazoles from abundant phenols and amines has been developed using TEMPO-controlled phenol functionalization. This method offers advantages in terms of generality, selectivity, efficiency, and atom-and-step economies over traditional methods.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Lebin Su, Shimin Xie, Jianyu Dong, Neng Pan, Shuang-Feng Yin, Yongbo Zhou
Summary: The cyclization-coupling reaction of 2-bromoaryl ketones and terminal alkynes is achieved for the first time by copper catalysis, producing polyfunctional naphthyl aryl ethers with broad substrate scope and good yields.
Article
Chemistry, Organic
Lebin Su, Shimin Xie, Jianyu Dong, Feng Liu, Shuang-Feng Yin, Yongbo Zhou
Summary: A copper(I)-catalyzed tandem reaction has been developed for the efficient synthesis of densely functionalized isoquinolines. This reaction combines N atom transfer and three-component cyclization, and demonstrates facile, highly selective, and general characteristics. The formation of aromatic C-N bonds and complete C-N triple bond cleavage are achieved in this reaction, possibly through the intermediates of Cu(III)-acetylide species enabling highly selective 6-endo-dig cyclization.
Article
Materials Science, Multidisciplinary
Hongyang Zhang, Zhao Chen, Longzhi Zhu, Yongquan Wu, Yuqing Xu, Shuming Chen, Wai-Yeung Wong
Summary: Researchers have achieved high external quantum efficiency in near-infrared OLEDs by designing new near-infrared phosphorescent Ir(III) complexes. The introduction of a cyano unit and a conjugated group improves the position of the emission spectrum and the rate of radiative decay.
ADVANCED OPTICAL MATERIALS
(2022)
Article
Engineering, Chemical
Lanqing Deng, Lang Chen, Liangdi Zhu, Yang Li, Jie Ou-Yang, Shaofeng Wu, Peng Chen, Sheng Shen, Junkang Guo, Yongbo Zhou, Chak-Tong Au, Shuang-Feng Yin
Summary: A direct, highly selective, and scalable method for photocatalytic synthesis of amides has been developed in this study. The method can be conducted under visible light and room temperature, using air as the oxidant.
CHEMICAL ENGINEERING SCIENCE
(2022)
Article
Chemistry, Organic
Fan Cao, Lulu Si, Shipan Xu, Longzhi Zhu, Yu Liu, Weifeng Xu, Ke-Wen Tang, Biquan Xiong, Wai-Yeung Wong
Summary: A pyridine-promoted diazotization of P-H bonds with aryl diazonium tetrafluoroborates is reported. The method is simple and efficient, providing azo organophosphorus compounds with excellent yields. It avoids the need for complex and harsh reaction conditions and the addition of oxides, and is tolerant to various functional groups. The synthesized azo organophosphorus compounds may find potential applications in organic chemistry and drug design.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Biquan Xiong, Lulu Si, Longzhi Zhu, Rong Wu, Yu Liu, Weifeng Xu, Fan Zhang, Ke-Wen Tang, Wai-Yeung Wong
Summary: A mild and efficient Zn(II)-catalyzed regioselective 1,6-hydroarylation of para-quinone methides (p-QMs) with electron-rich arenes protocol is reported. A variety of electron-rich arenes and para-quinone methides are well tolerated under mild conditions, delivering a broad range of triarylmethanes in good to excellent yields. The present method also works well for the hydroarylation of p-QMs with other nucleophiles, such as aniline, indole and phenol derivatives, offering the corresponding triarylmethanes with good yields under the standard conditions. The possible mechanism for the formation of C(sp(3))-C(sp(2)) bonds in hydroarylation reactions has been explored by step-by-step control experiments, and the reaction may follow a second-order manner in a chemical kinetic study.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Jia Yang, Lei Fan, Chen Chen, Mingyue Wang, Bingqian Sun, Shuai Wang, Hong Zhong, Yongbo Zhou
Summary: In this study, we developed an efficient Ni-catalyzed C-F bond phosphorylation of aryl fluorides using the intermediates of P-P(O) and P(O)OR. We observed that active aryl fluorides can generate organophosphorus compounds via P-P(O) mediation, while inactive aryl fluorides can also be activated and phosphorylated through a P(O)OR-mediated pathway, which has been rarely reported. The scalability to gram level and the possibility of upgrading bioactive molecules suggest promising applications of this protocol in synthetic chemistry.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Lixin Liu, Jianyu Dong, Zuqi Fu, Lebin Su, Shaofeng Wu, Qian Shang, Shuang-Feng Yin, Yongbo Zhou
Summary: In this study, a specific cross-dimerization of terminal alkynes is developed under Pd/TMEDA catalysis, which produces a series of gem-1,3-enynes with different functional group tolerance in moderate to high yields. The reaction features anti-addition-carbometallation, easy control of selectivity, wide range of donor alkynes, and simple catalytic conditions.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Lulu Si, Biquan Xiong, Shipan Xu, Longzhi Zhu, Yu Liu, Weifeng Xu, Ke-Wen Tang
Summary: A copper-catalyzed cross-dehydrogenative coupling reaction of P(O)-H compounds with O-/S-nucleophiles has been developed for the synthesis of phosphinates and phosphinothioates. The reaction tolerates a wide range of O- and S-nucleophiles, giving good to excellent yields of the target products. The protocol is effective and convenient, using inexpensive copper iodide as the catalyst and avoiding the use of hazardous and toxic reagents. Through control and competitive experiments, a plausible reaction mechanism has been proposed, suggesting a radical process.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Biquan Xiong, Lulu Si, Longzhi Zhu, Yu Liu, Weifeng Xu, Ke-Wen Tang, Shuang-Feng Yin, Peng-Cheng Qian, Wai-Yeung Wong
Summary: A copper-catalyzed aerobic oxidative/decarboxylative phosphorylation of aryl acrylic acids with P(III)-nucleophiles via the Michaelis-Arbuzov rearrangement is reported. The reaction can be carried out effectively without the use of a ligand and a base. Various aryl acrylic acids and P(III)-nucleophiles are compatible in this transformation, providing β-keto-organophosphorus compounds with good to excellent yields. The possible mechanism and kinetic studies show that this transformation may proceed through second-order chemical kinetics and involves a radical process.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Wenli Shang, Longzhi Zhu, Zikang Li, Weifeng Xu, Biquan Xiong, Yu Liu, Ke-Wen Tang, Peng-Cheng Qian, Shuang-Feng Yin, Wai-Yeung Wong
Summary: A simple and efficient method for the ruthenium-catalyzed 1,6-hydroalkylation of para-quinone methides with ketones via in situ activation of C-(sp(3))-H bonds has been disclosed. This method demonstrates good substrate tolerance and moderate to good yields of the desired 1,6-hydroalkylation products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Furong Geng, Shaofeng Wu, Xinyang Gan, Wenjuan Hou, Jianyu Dong, Yongbo Zhou
Summary: A facile synthesis of 1H-imidazoles has been developed through direct oxidative annulation of aryl methyl ketones and primary amines in the presence of TEMPO under weakly acidic conditions. This method enables the synthesis of 2H-imidazole skeletons from ketones for the first time by replacing amines with ammonium acetate. Various functional groups can be easily transformed into desired products, and the potential application of this method has been verified through scale-up synthesis and Sonogashira coupling functionalization of imidazoles.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Shaofeng Wu, Furong Geng, Jianyu Dong, Long Liu, Lebin Su, Yongbo Zhou
Summary: A general and practical method for the synthesis of naphtho[2,1-d]oxazoles from readily available naphthols and amines has been developed. This method shows outstanding functional group tolerance and is particularly suitable for the synthesis of naphtho[2,1-d]oxazole skeletons that are difficult to be prepared by other methods.
ORGANIC CHEMISTRY FRONTIERS
(2022)
