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, Multidisciplinary
Jasem Aboonajmi, Farhad Panahi, Hashem Sharghi
Summary: The multicomponent coupling reaction using Fe(III) catalyst precursor to mix catechol, ammonium acetate, and benzyl alcohol/benzyl methyl ether produced benzoxazole derivatives with good to excellent yields. The protocol stands out for the availability of the catalyst system, potential for large-scale synthesis, high diversity of products, and high yields.
Article
Nanoscience & Nanotechnology
Sourav Kumar, Manoj Kumar, Vandana Bhalla
Summary: Supramolecular assemblies of Im-Tpy with phenanthro[9,10-d]imidazole as the donor and terpyridyl group as the acceptor have been developed to stabilize Co(II) in its nanoform. The resulting nanoensemble shows high thermal and photostability, and exhibits efficient catalytic activity for the oxidation of alcohols using visible light radiation as the energy source.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Organic
Mugada Sugunakara Rao, Sahid Hussain
Summary: This study presents a simple and efficient TEMPO-mediated system for the aerobic oxidative synthesis of 2-aryl benzoxazoles from readily available benzoxazoles and primary benzylic and hetero benzylic amines. The reactions proceed through ring-opening of benzoxazoles followed by oxidative condensation with benzylamines, yielding moderate to good yields with a variety of substrates under mild conditions using air as an external green oxidant.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Daichi Yamane, Haruna Tanaka, Akihiro Hirata, Yumiko Tamura, Daichi Takahashi, Yusuke Takahashi, Tohru Nagamitsu, Masaki Ohtawa
Summary: A highly efficient one-pot gamma-lactonization of homopropargyl alcohols has been developed via an alkyne deprotonation/boronation/oxidation sequence. The oxidation of alkynyl boronate leads to the formation of ketene intermediate, which then reacts with the adjacent hydroxy group to produce the gamma-lactone. Optimization of conditions and exploration of substrate scope and synthetic applications have been conducted for this efficient one-pot lactonization reaction.
Article
Biochemistry & Molecular Biology
Zeng-Jie Yang, Qing-Tian Gong, Yuan Yu, Wei-Fan Lu, Zhe-Ning Wu, Na Wang, Xiao-Qi Yu
Summary: By combining enzymatic and visible-light catalysis, an efficient and green method for synthesizing 2-substituted benzothiazoles has been developed, achieving high yields in a short amount of time with nearly 100% atomic utilization. This method showcases the potential of harnessing the catalytic activity of enzymes and visible light for organic synthesis, without the need for additional oxidants or metals, making it environmentally friendly.
BIOORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Yuan Yu, Wei-Fan Lu, Zeng-Jie Yang, Na Wang, Xiao-Qi Yu
Summary: A novel strategy combining visible-light and enzyme catalysis was successfully applied for the synthesis of 4H-pyrimido [2,1-b] benzothiazole derivatives in one pot, achieving high yields and easy operation. By utilizing a photoorgano catalyst and enzyme, alcohols were efficiently oxidized into aldehydes, leading to a more efficient and eco-friendly approach for the synthesis of 4H-pyrimido [2,1-b] benzothiazole derivatives.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Tianzhen Li, Zijian Tan, Zijing Tang, Pi Liu, Haifeng Liu, Leilei Zhu, Yanhe Ma
Summary: An efficient method for synthesizing glycolic acid was reported in this study, utilizing a catalytic C-C coupling reaction of formaldehyde and selective oxidation, with an evolved enzyme showing improved activity at high formaldehyde concentrations.
Article
Multidisciplinary Sciences
Talshyn Begildayeva, Ahreum Ahn, Shreyanka Shankar Naik, Seung Jun Lee, Jayaraman Theerthagiri, Tae Ho Kim, Myong Yong Choi
Summary: Different nitrile solvents were investigated for CuCN formation through quantum chemical calculations, leading to the development of a new PLAL method. Acetonitrile yielded CuCN with a cube-like structure, while other solvents produced spherical Cu@GC nanoparticles. The theoretical study on binding energies of nitrile solvents was confirmed by basic sets of B3LYP and MP2, consistent with experimental outcomes for potential applications in novel metal-polymer materials.
SCIENTIFIC REPORTS
(2021)
Article
Chemistry, Multidisciplinary
Francesco Nocito, Ilaria Orlando, Francesca Digioia, Michele Aresta, Angela Dibenedetto
Summary: This study describes the synthesis and application of mixed oxides as catalysts for the one-pot conversion of nonedible oils into C9 mono- and dicarboxylic acids, providing a cost-effective, recoverable, and reusable method for producing valuable products with potential applications in various industries. The research also highlights the use of oxygen as an oxidant, the elimination of sulfuric acid in esterification/transesterification, and the use of a single catalyst for both oxidation and esterification reactions, marking significant innovations in the field.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Organic
Miseon Choi, Manish Kumar Mehra, Chung Whan Lee
Summary: Various indolo[2,3-b]indoles can be synthesized in one pot through a copper-catalyzed transformation of easily accessible 2-(substituted-amino)aryl)(mesityl)iodonium salts and indole derivatives. The reaction exhibits excellent functional group toleration and provides a series of indolo[2,3-b]indole derivatives in good yields. Moreover, direct access to benzoxazole derivatives can be achieved through intramolecular cyclization of 2-(substituted-amino)aryl)(mesityl)iodonium salts in the presence of copper catalyst.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
James S. Sharley, Guido Gambacorta, Ana Maria Collado Perez, Estela Espinos Ferri, Amadeo Fernandez Miranda, Isabelle Fernandez Fernandez, Jorge Sanchez Quesada, Ian R. Baxendale
Summary: A new method for the oxidation of Hedione 1 to dehydrohedione 2 has been developed based on a one-pot alpha-chlorination-elimination sequence, which allows for easy scalability. The unprecedented spontaneous elimination of alpha-chloro in methanol enables the oxidation to be carried out as a one-pot protocol, eliminating the need for multiple steps/reactions. A continuous flow process utilizing sulfuryl chloride has also been demonstrated, providing a steady and safe evolution of SO2 gas during the reaction.
Article
Engineering, Chemical
Ahmad Shaabani, Mostafa M. Amini, Mehrdad Shadi, Fereshteh Bahri, Masoumeh Karimi Alavijeh, Hassan Farhid
Summary: By chemically functionalizing MIL-101-NH2 with CoTSPc through superior electrostatic interaction reaction, a spongy composite with excellent catalytic activity in oxidation reaction has been successfully synthesized. The composite shows promising potential for practical applications.
JOURNAL OF THE TAIWAN INSTITUTE OF CHEMICAL ENGINEERS
(2021)
Article
Chemistry, Multidisciplinary
Foad Kazemi, Yadollah Shariati, Babak Kaboudin
Summary: This paper reports a simple, metal-free, and homogeneous two-step one-pot method for the synthesis of α-aminophosphonate using alcohol as a starting material and tetrabutylammonium tribromide (TBATB) as a catalyst. The reaction shows efficient catalytic effects for both photo tunable aerobic oxidation of alcohol and synthesis of α-aminophosphonate from in situ prepared aldehyde.
Article
Engineering, Chemical
Shalaka S. Mohire, Ganapati D. Yadav
Summary: In this study, we optimized a method for the one-pot synthesis of benzimidazole using a bimetallic catalyst supported by meso-cellular foam (MCF). The catalyst exhibited bifunctionality, allowing for the hydrogenation of o-nitroaniline to o-phenylenediamine (OPDA) and the cyclization of OPDA into benzimidazole. The use of a solvent mixture provided an in situ source of hydrogen and carbon dioxide, which played a significant role in the reaction. The synthesized catalyst was characterized and the reaction mechanism and kinetics were established.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
(2022)
Article
Chemistry, Organic
Jiye Jeon, Hyung Joo Kim, Cheol-Hong Cheon
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Young-In Jo, Chun-Young Lee, Cheol-Hong Cheon
Article
Chemistry, Organic
Young-In Jo, Chun-Young Lee, Cheol-Hong Cheon
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Hyung Joo Kim, Cheol-Hong Cheon
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Analytical
Yeongseok Chae, Sein Min, Eunjoon Park, Chaiho Lim, Cheol-Hong Cheon, Keunhong Jeong, Kyungwon Kwak, Minhaeng Cho
Summary: The integration of flow cells with NMR and FTIR systems allows for real-time observation of reaction intermediates, offering a valuable tool for elucidating reaction mechanisms and obtaining elusive kinetic data. By combining the sensitivity of IR spectroscopy with the quantitative analysis capabilities of NMR, this approach enables comprehensive evaluation of reaction processes, including potentially hazardous reactions, without direct contact with harmful intermediates.
ANALYTICAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Eunjoon Park, Jina Park, Cheol-Hong Cheon
Summary: This study discusses the distinct reactivity between cyanide and NHC with 4-(2-formylphenoxy) but-2-enoate derivatives.
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Eunjoon Park, Cheolwoo Bae, Cheon-Gyu Cho, Cheol-Hong Cheon
Summary: The total syntheses of the antirhine alkaloids were achieved through a series of reactions, including the cyanide-catalyzed imino-Stetter reaction and subsequent C-ring formation to generate the key intermediate. The trans-selective installation of the homoallylic alcohol side-chain at C-15 allowed the successful total syntheses of antirhine and its known epimer.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jiye Jeon, Sang Eun Lee, Cheol-Hong Cheon
Summary: The total synthesis of (+/-)-hinckdentine A was achieved through a cyanide-catalyzed imino-Stetter reaction and oxidative rearrangement, followed by D-ring formation and seven-membered C-ring construction. The newly synthesized compound contains all functional groups correctly positioned in the natural product.
Article
Chemistry, Organic
Jinjae Park, Cheol-Hong Cheon
Summary: This study reports a concise total synthesis of rucaparib, an FDA-approved drug for ovarian and prostate cancers. The desired structure was achieved through key reactions, and the final compound was obtained with commercially available starting materials in a simple procedure, resulting in a high overall yield.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sangmin Song, Seung-Hoon Um, Jaeho Park, Inho Ha, Jaehong Lee, Seongchan Kim, Hyojin Lee, Cheol-Hong Cheon, Seung Hwan Ko, Yu-Chan Kim, Hojeong Jeon
Summary: The study introduces a rapid synthesis method using a laser-induced hydrothermal process to synthesize hydroxyapatite particles ranging from nanometer to micrometer scale in seconds. This method allows selective metal ion substitution into the apatite matrix with controllable concentration. The synthesized powders show enhanced bone cell attachment and proliferation ability.
Article
Chemistry, Organic
Jiye Jeon, Cheol-Hong Cheon
Summary: In this paper, the first asymmetric total synthesis of iheyamine B from 2,2'-bisindoloazepinone is reported, which involves the stereoselective construction of the trans-vicinal 2-oxopropyl moiety in the azepine scaffold.
Article
Chemistry, Organic
Ju Hyeon Park, Jinjae Park, Cheol-Hong Cheon
Summary: A protocol for the synthesis of 2-(2-nitrophenyl)indoline-3-acetic acid derivatives was developed via base-catalyzed cyclization of N-(2-nitrobenzyl)-2-aminocinnamic acid derivatives. The synthetic utility of this methodology was illustrated by the concise synthesis of dihydropaullone, a partially saturated analog of paullone. Furthermore, the indoline scaffold could be further converted to the corresponding indoles and other indole-fused heterocycles.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Jinjae Park, Tae Lyn Kim, Cheol-Hong Cheon
Summary: In this paper, we discuss the recent progress made by our research group in the total synthesis of several 2,2'-biindolyl natural products using the cyanide-catalyzed imino-Stetter reaction. We describe a novel protocol for accessing 2,2'-bisindole-3-acetic acid derivatives via this reaction and the application of this method in the total synthesis of class I, class II, and class III 2,2'-biindolyl natural products.
Article
Chemistry, Multidisciplinary
Jinjae Park, Cheol-Hong Cheon
Summary: Two routes for the synthesis of rucaparib have been developed, using commercially available starting materials and the cyanide-catalyzed imino-Stetter reaction as the key step. The second-generation synthesis achieved a higher overall yield and resolved issues from the first-generation synthesis.
Article
Chemistry, Physical
Myeong-Geun Kim, Youngjo Choi, Eunjoon Park, Cheol-Hong Cheon, Nak-Kyoon Kim, Byoung Koun Min, Woong Kim
ACS APPLIED ENERGY MATERIALS
(2020)
