Article
Chemistry, Organic
Hua Yao, Xiaoyang Zhong, Bingqing Wang, Sen Lin, Zhaohua Yan
Summary: A novel and efficient approach for the amine-directed dehydrogenative C(sp(2))-C(sp(3)) coupling of arylamines with acetonitrile was developed using FeCl2 as the catalyst. The method provides a straightforward and green route to arylacetonitriles with good regioselectivity and excellent compatibility of functional groups and aromatic rings.
Article
Chemistry, Organic
Ruoqian Fan, Meiying Kuai, Dong Lin, Felix Bauer, Weiwei Fang
Summary: A new palladacyclic N-heterocyclic carbene pre-catalyst was designed and successfully applied for Pd-catalyzed C-N cross-coupling reactions of challenging heteroaryl chlorides. The desired aminated products were achieved in good to excellent yields.
Article
Chemistry, Applied
Youhei Takeda, Kazuya Toyoda, W. M. C. Sameera, Norimitsu Tohnai, Satoshi Minakata
Summary: A novel palladium-catalyzed regioselective and enantiospecific ring-opening Suzuki-Miyaura arylative cross-coupling has been developed to synthesize enantioenriched 3,3-diarylpropylamines. The mechanism of the reaction was rationalized using density functional theory, with transition states of the selectivity-determining ring-opening step systematically determined by the multi-component artificial force induced reaction (MC-AFIR) method to explain the regioselectivity of the reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Inorganic & Nuclear
Xiaoxiao Cui, Xiujia Hao, Fang Guo
Summary: This paper describes the synthesis of three N-heterocyclic carbene complexes by stepwise grinding and their application as catalysts in C-S bond cross-coupling reactions.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Physical
Guang-Yan Xing, Ya-Cheng Zhu, Deng-Yuan Li, Pei-Nian Liu
Summary: On-surface synthesis, a powerful tool for atomically precise fabrication of low-dimensional carbon nanomaterials, has greatly enriched fundamental science and technology. Achieving high selectivity of covalent coupling reactions remains challenging due to the complicated reactivity of organic groups and irreversibility of covalent bonds. Only a few on-surface covalent coupling reactions are frequently used, and this Perspective focuses on the development and synthetic applications of on-surface cross-coupling reactions.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Organic
Xianglong Chu, Yadi Niu, Xiaodong Wang, Yunliang Lin, Fuwei Li, Chen Ma
Summary: A rapid method for preparing a series of N-heteroarene fluorophores via palladium-catalyzed direct oxidative reactions has been developed, showing color-tunable emissions and high fluorescence quantum yields. The photophysical properties-structure relationship was systematically investigated, leading to the discovery of fluorophores with emissions ranging from 431-507 nm in CH2Cl2 and fluorescence quantum yields up to 91% in CH2Cl2.
SYNTHESIS-STUTTGART
(2021)
Review
Environmental Sciences
Govardhana Reddy Peddiahgari Vasu, Krishna Reddy Motakatla Venkata, Raghava Reddy Kakarla, Kalluri V. S. Ranganath, Tejraj M. Aminabhavi
Summary: This article explores the research of Pd-PEPPSI complexes in recent years, introducing the synthesis of these catalysts and their applications in various reactions. The article also discusses the reusable heterogeneous PdPEPPSI complexes and their catalytic applications, and concludes with a discussion on chiral Pd complexes and their asymmetric transformations.
ENVIRONMENTAL RESEARCH
(2023)
Article
Chemistry, Organic
Dinda B. Pitna, Nao Tanaka, Toyonobu Usuki
Summary: Using a heterogeneous Pd/C catalyst, consecutive Suzuki-Miyaura cross-coupling and hydrogenation reactions were successfully carried out in one pot with excellent yield starting from bromopyridines and methoxyphenyl boronic acid. The addition of an appropriate amount of H2O was crucial for successful AcOH-promoted hydrogenation, ensuring selective reduction of the pyridine rings to piperidines while countering Pd leaching and catalyst poisoning.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yahao Dong, Fengjun Xue, Yuping Wei
Summary: This study designed and prepared an eco-friendly magnetic palladium catalyst with excellent catalytic activity, easy recovery, high thermal stability, and low toxicity, providing new possibilities for the application of magnetic materials in green organic catalysis.
JOURNAL OF PHYSICS AND CHEMISTRY OF SOLIDS
(2021)
Article
Chemistry, Multidisciplinary
Xinlan A. F. Cook, Loic R. E. Pantaine, David C. Blakemore, Ian B. Moses, Neal W. Sach, Andre Shavnya, Michael C. Willis
Summary: Heteroaromatic sulfinates are effective nucleophilic reagents in Pd-0-catalyzed cross-coupling reactions with aryl halides. Base-activated, latent sulfinate reagents, such as beta-nitrile and beta-ester sulfones, have been introduced to address challenges in purifying and solubilizing metal sulfinate salts, as well as their tolerance to multi-step transformations. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration and amenable to scale-up processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jun Chen, Yu-Jie Liang, Peng-Zi Wang, Guo-Qing Li, Bin Zhang, Hao Qian, Xiao-Die Huan, Wei Guan, Wen-Jing Xiao, Jia-Rong Chen
Summary: This study presents a photoinduced copper-catalyzed cross-coupling reaction for the generation of allylic esters. The reaction proceeds at room temperature with high regio- and enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
Myuto Kashihara, Yoshiaki Nakao
Summary: Cross-coupling reactions using nitroarenes as electrophiles have gained attention due to their ease of accessibility and potential advantages over haloarenes. Recent research has focused on developing new catalyst systems and reaction conditions to improve the efficiency and practicality of these reactions, with promising results in diversifying bond-forming reactions and reducing catalyst loading. Research in this field is expected to continue growing as the utility of nitroarenes in organic synthesis is reevaluated.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Review
Chemistry, Multidisciplinary
Xinlan A. F. Cook, Antoine de Gombert, Janette McKnight, Loic R. E. Pantaine, Michael C. Willis
Summary: This review focuses on the methods developed for the challenging coupling of 2-pyridine nucleophiles with (hetero)aryl electrophiles, ranging from traditional cross-coupling processes to alternative nucleophilic reagents and novel main group approaches.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Lukas Hoff, Simon D. Schnell, Andrea Tomio, Anthony Linden, Karl Gademann
Summary: A silver-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids was presented in this study. It was found that electronic modification of the dppf ligand played a crucial role in achieving good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl- and heteroaryl-tetrazines were successfully prepared, with yields up to 87%.
Review
Chemistry, Multidisciplinary
Emily K. Reeves, Emily D. Entz, Sharon R. Neufeldt
Summary: Chemodivergent cross-couplings refer to reactions in which one potentially reactive functional group can be made to react based on choice of conditions. Factors influencing selectivity include catalyst ligation state, solvent polarity, and metal identity.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Biochemistry & Molecular Biology
Ayaka Ueda, Yusuke Aihara, Shinya Sato, Keiko Kano, Emi Mishiro-Sato, Hiroyuki Kitano, Ayato Sato, Kazuhiro J. Fujimoto, Takeshi Yanai, Kazuma Amaike, Toshinori Kinoshita, Kenichiro Itami
Summary: This study discovered 2,6-dihalopurines as a new inhibitor of stomatal opening and investigated its mechanism. Biological assays suggested that the pathway related to plasma membrane H+-ATPase phosphorylation may be involved. Through affinity-based pull down assay and molecular dynamics simulation, Leucine-rich repeat extensin proteins (LRXs), LRX3, LRX4, LRX5, and RALF were identified as target protein candidates for 2,6-dihalopurines. The mechanism of stomatal movement related to LRXs-RALF is an unexplored pathway, and further studies may uncover new signaling pathways and regulatory factors in stomatal movement.
ACS CHEMICAL BIOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Ayaka Ueda, Kazuma Amaike, Yoko Shirotani, Hideto Ito, Robin Warstat, Jae-Hoon Choi, Hirokazu Kawagishi, Kenichiro Itami
Summary: Imidazole-4-carboxamide (ICA), a type of fairy chemical (FCs) causing fairy ring phenomena, exhibits plant growth inhibitory activity. FCs have the potential to be a new family of plant hormones as they are endogenous in all tested plant species and regulate plant growth. This study focuses on the synthesis of ICA derivatives and evaluation of their activity in rice. Surprisingly, several compounds show unexpected elongation activity in root and shoot growth.
CANADIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Kou P. Kawahara, Hideto Ito, Kenichiro Itami
Summary: We have developed a sulfur-embedding annulative pi-extension (thia-APEX) reaction to efficiently construct a sulfur-embedding cationic hexagonal aromatic ring called thiopyrylium onto unfunctionalized aromatics in a one-step process. The key of the thia-APEX reaction lies in the utilization of S-imidated ortho-arenoyl arenethiols, enabling easy synthesis of diverse pi-extended thiopyryliums. The synthesized thiopyryliums exhibit various absorption and emission properties across the visible light to NIR region, depending on minor structural variations.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Wataru Matsuoka, Kou P. Kawahara, Hideto Ito, David Sarlah, Kenichiro Itami
Summary: In this study, we successfully achieved a late-stage pi-extension of rubrene using dearomative annulative pi-extension (DAPEX), leading to the generation of rubrene derivatives with an extended aromatic core. These pi-extended rubrenes displayed a marked red shift in absorption and emission spectra, indicating the extension of the rubrene's aromatic pi-system both structurally and electronically. Furthermore, organic field-effect transistor devices using two-side pi-extended rubrene were fabricated, demonstrating the potential utility of these compounds in organic electronics with a comparable carrier mobility to rubrene thin-film transistors.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Nobushige Kai, Hideya Kono, Akiko Yagi, Kenichiro Itami
Summary: A novel structurally constrained nanobelt, methylene bridged [6]cyclo-2,6-naphthylene ([6]MCN), was synthesized via the nickel-mediated intramolecular aryl-aryl coupling of a triflated prism[6]arene. The structural and electronic properties of [6]MCN were characterized using NMR studies and photophysical measurements. In contrast to methylene-bridged [6]cycloparaphenylene, our previously synthesized benzene-based analogue, [6]MCN exhibited low strain energy (77.4 kcalmiddotmol(-1)) and bright fluorescence (Phi = 0.20).
Article
Chemistry, Multidisciplinary
Hiroshi Nonaka, Takeharu Mino, Seiji Sakamoto, Jae Hoon Oh, Yu Watanabe, Mamoru Ishikawa, Akihiro Tsushima, Kazuma Amaike, Shigeki Kiyonaka, Tomonori Tamura, A. Radu Aricescu, Wataru Kakegawa, Eriko Miura, Michisuke Yuzaki, Itaru Hamachi
Summary: Various small molecules have been used in medical diagnosis and disease treatment. However, evaluating the spatial distribution and kinetics of these molecules in complex tissues, such as the brain, has been challenging. This study introduces a new method called FixEL, which utilizes protein-MOI interactions and chemical cross-linking to trap and image exogenously administered molecules in complex tissues, providing valuable information on their distribution, binding selectivity, and diffusion/retention kinetics.
Article
Chemistry, Medicinal
Aya Ogata, Takashi Yamada, Saori Hattori, Hiroshi Ikenuma, Junichiro Abe, Mari Tada, Masanori Ichise, Masaaki Suzuki, Kengo Ito, Takashi Kato, Kazuma Amaike, Tsuyoshi Hirota, Akiyoshi Kakita, Kenichiro Itami, Yasuyuki Kimura
Summary: Positron emission tomography (PET) is a powerful imaging tool for early detection of Alzheimer's disease (AD) that has been developed to target beta-amyloid and tau protein aggregates. This study focuses on the development of a new PET ligand targeting protein kinase CK2, which is known to be altered in AD brains.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Hideya Kono, Yuanming Li, Guglielmo Monaco, Riccardo Zanasi, Francesco F. Summa, Lawrence T. Scott, Akiko Yagi, Kenichiro Itami
Summary: Cycloparaphenylenes (CPPs) and carbon nanobelts (CNBs) are cyclic molecular nanocarbons with unique properties derived from rigid, strained, and cyclic p-conjugated systems. The synthesis of various sizes of CPPs and CNBs has allowed for the investigation of their size-dependent properties and use in various applications. The synthesis, size-dependent properties, and paratropic belt currents of methylene-bridged [n]cycloparaphenylenes ([n]MCPP, n = 6, 8, 10) were reported and studied.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Kanna Fujishiro, Yuta Morinaka, Yohei Ono, Tsuyoshi Tanaka, Lawrence T. Scott, Hideto Ito, Kenichiro Itami
Summary: In this study, a lithium(0)-mediated mechanochemical anionic cyclodehydrogenation reaction was developed for the first time. The reaction could be easily performed using a conventional and easy-to-handle lithium(0) wire at room temperature, even under air, and achieved high yields in a short time. The study also comprehensively investigated the applicability and practicality of the protocol, as well as limitations, through computational studies and nuclear magnetic resonance analysis. Furthermore, novel nanographenes, including quinterrylene, were successfully synthesized using this method.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Takaku Yoshihara, Hiroki Shudo, Akiko Yagi, Kenichiro Itami
Summary: Peripheral structural modifications of arenes have a significant impact on their optoelectronic properties, molecular assembly, and stability. Annulation with an adamantane scaffold is a simple yet powerful modification strategy that leads to unique effects, such as high solubility and enhanced conjugation. The oxidation of adamantane-annulated perylenes produces cationic species with extended emission in the near-infrared region, potentially contributing to the development of groundbreaking pi-materials and novel nanocarbon materials.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Plant Sciences
Yuki Nakashima, Yuka Kobayashi, Mizuki Murao, Rika Kato, Hitoshi Endo, Asuka Higo, Rie Iwasaki, Mikiko Kojima, Yumiko Takebayashi, Ayato Sato, Mika Nomoto, Hitoshi Sakakibara, Yasuomi Tada, Kenichiro Itami, Seisuke Kimura, Shinya Hagihara, Keiko U. U. Torii, Naoyuki Uchida
Summary: A compound called PLU has been discovered to induce the formation of pluripotent callus in plants without the need for external hormone application. The PLU-induced callus expresses marker genes associated with pluripotency acquisition. This study provides a new approach to manipulate and investigate the induction of plant pluripotency.
FRONTIERS IN PLANT SCIENCE
(2023)
Article
Chemistry, Organic
Jaehyun Jung, Takumi Kinoshita, Yuta Makihara, Yota Sakakibara, Kazuma Amaike, Kei Murakami, Kenichiro Itami
Summary: In this study, a decarboxylative aminomethylation of aryl bromides with N-protected glycine under nickel/photoredox-catalyzed conditions was reported. The resulting products can be easily deprotected under acidic conditions to give primary benzylamines.
Article
Chemistry, Organic
Kou P. Kawahara, Hideto Ito, Kenichiro Itami
Summary: This paper describes the synthesis of pi-extended thianthrene derivatives from unfunctionalized aromatics using thia-APEX reactions. The reaction involves the fusion of new benzodithiine arms to the aromatic substrates in one step, resulting in the formation of pi-extended thianthrenes with yields ranging from 21% to 87%. The reaction requires equimolar amounts of the aromatic substrates and S-diimidated 1,2-arenedithiols, along with a catalytic amount of TfOH, and the synthesized pi-extended thianthrenes were characterized for their solid state packing structures and photophysical properties.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
