Article
Chemistry, Multidisciplinary
Yusuke Morino, Takafumi Yatabe, Kosuke Suzuki, Kazuya Yamaguchi
Summary: The efficient aerobic oxidative esterification of ethylene glycol to various oxalic acid diesters has been achieved using CuCl/tetramethylethylenediamine/1,5-dimethyl-9-azanoradamantane N-oxyl catalyst. The reaction shows high selectivity for ethylene glycol-derived alcohols/hemiacetals even in the presence of other aliphatic primary alcohols, and the efficient esterification is enabled by the preferential bidentate coordination of ethylene glycol-derived alcohols/hemiacetals to the Cu(ii) species.
Article
Chemistry, Inorganic & Nuclear
Wei Zhong, Jiabin Luo, Zhenzhen Liu, Guangli Zhan, Lihua Zhu, Chunxin Lu, Zhongquan Shen, Xueming Li, Xiaoming Liu
Summary: This study investigated the mechanistic aspects of CuI-catalyzed aerobic oxidation of alcohols using N,N,N',N'-tetramethylethylenediamine (TMEDA) as a ligand and 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) as a co-catalyst. The system exhibited excellent catalytic activity for selective oxidation of primary alcohols, yielding quantitative results on a preparative scale. Through mechanistic investigation, two binuclear copper complexes (1 and 2) were isolated, with 1 being an intermediate in the catalytic cycle initiated by CuI. However, an independent catalytic pathway was observed for complex 2, which maintained its dinuclear integrity throughout the process.
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Shelby M. Anderson, Marcus D. Van Engen, Paul E. Floreancig
Summary: The sequential allylic alcohol transposition, carbonyl group trapping, oxocarbenium ion formation, and nucleophilic addition result in ring formation and serve as a fragment-coupling and stereocenter-generating reaction. Balancing the kinetics of productive and unproductive steps is crucial for successful applications, and solvent changes can be used to expand the scope and change the stereochemical outcomes of the processes. Mechanistic studies provide insight into the transformations and reactive species generated.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jordan E. Nutting, Kaining Mao, Shannon S. Stahl
Summary: The study reveals different mechanistic differences between Cu/aminoxyl and Fe/aminoxyl catalyst systems, leading to distinct alcohol oxidation chemoselectivity and functional group compatibility. The Fe/aminoxyl system involves a redox cascade reaction, while the Cu/aminoxyl system exhibits integrated cooperativity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Kenneth M. Doll, Steven C. Cermak
Summary: A new electrochemical catalyst has been synthesized using an analog of TEMPO and undecenoic acid. This catalyst shows higher selectivity and reaction rates, indicating its potential for synthesizing high biobased content electroactive materials.
Article
Chemistry, Multidisciplinary
Sylvain Lemaitre, Anne-Lise Romain, Francois Bariere, Anthony Craquelin, Chloe Copin, Alexandre Jean
Summary: In the pharmaceutical industry, the development of a safe, cost-effective, productive, and sustainable process is crucial to minimize the negative environmental impact caused by the large-scale use of reagents and solvents. This study presents the successful replacement of a toxic and expensive oxidant with a highly efficient, selective, and environmentally friendly catalytic system for the oxidation of a benzylic primary alcohol in the manufacturing route of a clinical candidate. The implementation of this atom economical and low-cost aerobic oxidation at the pilot scale resulted in the production of a high-quality key intermediate.
Article
Engineering, Chemical
Jiaming Hu, Yongkang Zhu, Hu Gao, Feng Zhang, Zhibing Zhang
Summary: A scalable, continuous flow synthesis method for the aerobic oxidation of alcohols using a copper catalyst and molecular oxygen was developed, showing high yield of benzaldehyde by optimizing conditions. The method demonstrated fast reaction kinetics and a simplified kinetic model in a microchannel reactor.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Raul L. L. Carmo, Samuel L. Galster, Tomasz Wdowik, Chaeeon Song, Sherry R. Chemler
Summary: We report a catalytic enantioselective alkene aminooxygenation and dioxygenation method for the direct synthesis of enantioenriched2-formyl saturated heterocycles under aerobic conditions. Cyclic sulfonamides and alkenols are employed as substrates and readily available chiral copper complexes serve as catalysts. The reaction enables the preparation of various chiral nitrogen and oxygen heterocycles. These methods provide access to saturated heterocycles functionalized with carbonyl electrophiles, which are common components of bioactive small molecules.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Multidisciplinary Sciences
Yujing Li, Huihui Luo, Shuo Wang, Lei Li, Guosong Li, Wen Dai
Summary: An efficient protocol for the oxidative cleavage of C-C bonds in alkynes using heterogeneous cobalt nanoparticles as catalyst with molecular oxygen as the oxidant has been developed. A diverse set of mono- and multisubstituted aromatic and aliphatic alkynes can be effectively cleaved and converted into esters. The high surface area and pore volume, as well as the nanostructured nitrogen-doped graphene-layer coated cobalt nanoparticles, are possibly responsible for excellent catalytic activity.
Article
Chemistry, Multidisciplinary
Katrin Warm, Guilherme Tripodi, Erik Andris, Stefan Mebs, Uwe Kuhlmann, Holger Dau, Peter Hildebrandt, Jana Roithova, Kallol Ray
Summary: The Cu-I/TEMPO catalyst system has been shown to selectively yield aldehydes in aerobic alcohol oxidation reactions. By detecting reactive intermediates and conducting kinetic studies, the mechanisms of O-2 reduction and alcohol oxidation reactions have been clarified. This study provides valuable insights into the aerobic oxidation of alcohols and transition-metal catalysts involving redox-active organic cocatalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Vasut Nakarajouyphon, Thanthapatra Bunchuay, Nobuto Yoshinari, Takumi Konno, Preeyanuch Sangtrirutnugul
Summary: In this study, amphiphilic tris(triazolyl)amines functionalized with poly(ethylene glycol) were investigated as bi-functional surfactants for copper-catalyzed aerobic alcohol oxidation in water. The results showed that NBBT550 exhibited the highest activity among the tested surfactants. However, there was significant leaching of copper ions from the catalyst system, leading to the need for additional copper catalyst after every four catalytic cycles.
NEW JOURNAL OF CHEMISTRY
(2022)
Review
Chemistry, Physical
Takahide Fukuyama, Baptiste Picard, Ilhyong Ryu
Summary: This paper summarizes our team's efforts over the past two decades in the development of new catalytic methods for C-C bond formation. The versatile applications of the commercially available catalyst RuHCl(CO)(PPh3)(3) (or RuH for short) are highlighted through eight different transformations. The fundamental steps involved in the catalysis are emphasized, demonstrating how our mechanistic understanding and the diverse catalytic capabilities of RuH can be utilized to design desired catalytic cycles and develop new cross-coupling reactions with high atom-economy.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Shi-Jun Li, Wei Fang, Jeremy O. Richardson, De-Cai Fang
Summary: Studies show that the low spin state of FeCl3/TEMPO is more favorable for hydrogen abstraction, with the N atom being the preferred hydrogen acceptor. It is discovered that dispersion interactions and nuclear tunneling can accelerate the reaction process.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Sanjay Singh, Sankalan Mondal, Nagaraju Vodnala, Chinmoy Kumar Hazra
Summary: In this study, unsymmetrical polyarylated alkanes were synthesized using a cheap, commercially available Bronsted acid-catalytic system (pTSA center dot H2O)/HFIP. The one-pot three-component approach avoided the use of pyrophoric reagents, metal catalysts, toxic solvents, or Grignard reagents, and showed high greenness in terms of various green metrics. The method was also applied for the synthesis of pharmaceuticals and natural product functionalization.
Article
Chemistry, Organic
Svitlana O. Sotnik, Andrii Subota, Anton Y. Kliuchynskyi, Dmytro Yehorov, Anton S. Lytvynenko, Alexander B. Rozhenko, Sergey Kolotilov, Sergey Ryabukhin, Dmitriy M. Volochnyuk
Summary: A Cu-catalyzed one-pot synthesis of fused pyridines from cyclic ketones and propargylamine was described, optimized based on over 30 experiments. The protocol is cost-effective and scalable, suitable for preparing large quantities of fused pyridine-based building blocks without requiring high-pressure autoclave technique. Adjusting the catalyst amount allowed comparable yields with longer reaction times, while the reaction conditions showed tolerance to various protective functional groups in ketones.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Peter Vamosi, Keiya Matsuo, Tsuguya Masuda, Kohei Sato, Tetsuo Narumi, Kazuhiro Takeda, Nobuyuki Mase
Article
Chemistry, Applied
Mohammad Nasir Uddin, Zainul Abedin Siddique, Nobuyuki Mase, Monir Uzzaman, Wahhida Shumi
APPLIED ORGANOMETALLIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Nobuyuki Mase, Moniruzzaman, Shoji Yamamoto, Kohei Sato, Tetsuo Narumi, Hikaru Yanai
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Organic
Ryuji Ide, Ryuji Kyan, Thien Phuc Le, Yuya Kitagawa, Kohei Sato, Nobuyuki Mase, Tetsuo Narumi
Article
Chemistry, Multidisciplinary
Ryuji Kyan, Kohei Sato, Nobuyuki Mase, Tetsuo Narumi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Organic
Takuya Iio, Kohei Nagai, Tomoki Kozuka, Akhtar Mst Sammi, Kohei Sato, Tetsuo Narumi, Nobuyuki Mase
Article
Chemistry, Analytical
Daigo Terutsuki, Hidefumi Mitsuno, Kohei Sato, Takeshi Sakurai, Nobuyuki Mase, Ryohei Kanzaki
ANALYTICA CHIMICA ACTA
(2020)
Article
Chemistry, Organic
Kohei Sato, Shoko Tanaka, Junzhen Wang, Kenya Ishikawa, Shugo Tsuda, Tetsuo Narumi, Taku Yoshiya, Nobuyuki Mase
Summary: The novel late-stage solubilization of peptides using hydrazides involves attaching a solubilizing tag through selective N-alkylation at a hydrazide moiety. The tag, which can tolerate ligation and desulfurization conditions, can be detached through a Cu-mediated selective oxidative hydrolysis of the N-alkyl hydrazide. This method was validated through the synthesis of HIV-1 protease.
Article
Chemistry, Organic
Ryuji Kyan, Yuya Kitagawa, Ryuji Ide, Kohei Sato, Nobuyuki Mase, Tetsuo Narumi
Summary: The study demonstrates the use of highly sterically hindered N-heterocyclic carbenes as catalysts in the cross-annulation reaction of alpha,beta-enals and aryl aldehydes, leading to the convergent construction of beta,gamma-trans-disubstituted gamma-butyrolactones.
Article
Chemistry, Organic
Yuki Kodama, Sayuri Takeo, Junko Fujimoto, Kohei Sato, Nobuyuki Mase, Tetsuo Narumi
Summary: This study presents the synthetic, spectroscopic, crystallographic, and computational analysis of a series of peptidomimetics containing L-Xaa-D-Yaa-type (Z)-chloroalkene dipeptide isosteres (CADIs). It is found that the 1,3-allylic strain across the chloroalkene moiety induces hyperconjugative interactions, contributing significantly to the stabilization of beta-turn structures.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Gary Morrison, Ruairi Bannon, Scott Wharry, Thomas S. Moody, Nobuyuki Mase, Masayuki Hattori, Haresh Manyar, Megan Smyth
Summary: Selective photooxidation of alkyl benzenes was studied in a custom-built continuous flow photochemical reactor. Fine bubbles of air were used as an oxidizing agent, and the reactor achieved high conversion and selectivity by improving the mass transfer efficiency.
TETRAHEDRON LETTERS
(2022)
Article
Polymer Science
Hoque Mohammed Jabedul, Mitsuo Toda, Nobuyuki Mase
Summary: Polyhemiaminal (PHA) polymers are a type of newly developed thermosetting polymers with high mechanical strength and excellent recycling properties. However, the low thermal stability of PHA polymers has been a common issue. In this study, crosslinked PHA polymer composites were synthesized and demonstrated to have good film formability and high thermal stability under optimal conditions.
Article
Chemistry, Multidisciplinary
Akira Kuwahara, Yuki Mizushima, Makoto Matsui, Tomoki Kozuka, Nobuyuki Mase
Summary: This study presents the first experimental evidence of direct H-2 production from seawater using multiphoton ionization water splitting with a femtosecond pulse laser, without harmful gas emissions. The H-2 production rate in seawater was 3.3 times higher compared to ultrapure water. The study also observed ion enhancement in seawater, but excessive salt can have adverse effects.
Article
Chemistry, Multidisciplinary
Yuki Kodama, Saki Imai, Junko Fujimoto, Kohei Sato, Nobuyuki Mase, Tetsuo Narumi
Summary: This study describes the first stereoselective synthesis of highly functionalized chloroalkene dipeptide isosteres containing an alpha,alpha-disubstituted amino acid (alpha alpha AA). The key step involves the construction of a quaternary carbon center through Aza-Darzens condensation, providing valuable compounds for the synthesis of various alpha alpha AA-containing chloroalkene isosteres.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Hikari Okita, Yuna Kato, Tatsuki Masuzawa, Kosuke Arai, Sayuri Takeo, Kohei Sato, Nobuyuki Mase, Takanori Oyoshi, Tetsuo Narumi
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
