Article
Chemistry, Multidisciplinary
Tosapol Maluangnont, Piyasan Praserthdam, Tawan Sooknoi
Summary: The cascade reaction of palmitic acid to hydrocarbons was investigated over different catalysts, and it was found that the layered alkali titanate catalysts exhibited higher activity and selectivity compared to TiO2 and Mg/Al mixed oxide catalysts. The reaction pathway and yield of hydrocarbons were influenced by temperature and the partial charge at the O atom.
Review
Chemistry, Multidisciplinary
Aleksa Kojcnovic, Blaz Likozar, Miha Grilc
Summary: This review article focuses on the heterogeneous catalytic conversion of carbon dioxide (CO2) to various compounds. It discusses the formation of alkyl carbonates, cyclic carbonates, carbamates, and carboxylic acids through carboxylation reactions. The article provides detailed elaboration on reaction conditions, catalysts, activity/selectivity, and comparison of results obtained from recent publications.
JOURNAL OF CO2 UTILIZATION
(2022)
Article
Chemistry, Multidisciplinary
Anh Vy Tran, Seok-Kyu Park, Hye Jin Lee, Tae Yong Kim, Younhwa Kim, Young-Woong Suh, Kwan-Young Lee, Yong Jin Kim, Jayeon Baek
Summary: Efficient ring-opening coupled with hydrogenation of 2,5-furan dicarboxylic acid to produce adipic acid was achieved using a recyclable Ru/Al2O3 catalyst and an ionic liquid, [MIM(CH2)(4)SO3H]I, which delivered 99% overall yield. The Ru/Al2O3 catalyst showed high efficiency for the conversion of FDCA, and the ionic liquid system exhibited superior activity and reduced corrosion problems compared to conventional catalytic systems.
Article
Chemistry, Organic
Mizuki Nishiwaki, Wei Xu, Naoya Kumagai
Summary: A chemoselective dehydrogenation protocol for benzylic amines using the TEtraQuinoline (TEQ)/FeCl2 complex catalyst was developed. By combining with 2 equiv of tert-butyl hydroperoxide, as low as 0.1 mol% catalyst loading was sufficient to convert primary and secondary benzylic amines to the corresponding imines and dimerized imines. The benzyl group on the nitrogen atom could be removed through subsequent hydrolysis of the imines, while nonaromatic carbon-carbon multiple bonds and the O-Bn group remained intact, providing a complementary deprotection procedure to reductive removal conditions exerted by Pd catalysis.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Michael A. Stevens, Annie L. Colebatch
Summary: This article examines modes of cooperativity and catalytic mechanisms in metal-metal cooperative catalysts by studying (de)hydrogenation processes and drawing lessons from the development of metal-ligand cooperative catalysts.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Anh Vy Tran, Seok-Kyu Park, Hye Jin Lee, Tae Yong Kim, Younhwa Kim, Young-Woong Suh, Kwan-Young Lee, Yong Jin Kim, Jayeon Baek
Summary: The production of adipic acid from 2,5-furandicarboxylic acid via tetrahydrofuran-2,5-dicarboxylic acid using a recyclable Ru/Al2O3 catalyst in ionic liquid solvent is demonstrated in this research article.
Article
Chemistry, Organic
Lona Dutta, S. S. Ramasastry
Summary: This study describes a new method for the synthesis of 3HQs under neutral conditions, which also represents the first intramolecular oxyamination of α,β-ynones. The synthetic utility of this method is demonstrated by successfully synthesizing japonine, its analogs, and rare quinoline derivatives.
Article
Chemistry, Multidisciplinary
Chun-Hong Hu, Yueqian Sang, Ya-Wei Yang, Wen-Wen Li, Hui-Lin Wang, ZiYing Zhang, Chen Ye, Li-Zhu Wu, Xiao-Song Xue, Yang Li
Summary: The article presents a solution to the challenge of direct decarboxylation, by utilizing a charge-transfer complex of aryl carboxylate that induces chemoselective decarboxylation to aryl radicals. This method offers potential for mild and versatile arylations in various fields.
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, Applied
Ken Okuno, Bun Chan, Seiji Shirakawa
Summary: Catalytic kinetic resolution is a reliable method for enantioselective synthesis of chiral molecules. However, it is challenging to perform kinetic resolution on racemic compounds with similar substituents at a chiral center. In this study, a kinetic resolution of a-allyl-a-propargyl carboxylic acids was achieved using a chiral bifunctional sulfide catalyst. The utility of the resulting optically active compounds was also demonstrated.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Dangui Wang, Wentao Zhang, Xunbo Lu, Hongwei Zhou, Fangrui Zhong
Summary: Novel cinchona alkaloid derived iodide catalysts were developed for the enantioselective oxidative alpha-amination of 2-oxindoles, providing various functionalized spiropyrrolidine oxindoles in high yields and with good enantioselectivities. This iodide/ROOH catalytic system features a one-step synthesis of a catalyst with multiple functionalities, ease of operation, and good scalability, thereby enriching the repertoire of iodide catalysis for enantioselective oxidative coupling reactions.
Article
Chemistry, Multidisciplinary
Enrico Bergamaschi, Danijela Lunic, Liam A. McLean, Melissa Hohenadel, Yi-Kai Chen, Christopher J. Teskey
Summary: This study demonstrates, for the first time, the ability to use light to distinguish between ketones and carboxylic acids in more complex molecules. By utilizing different activation modes, a single catalytic system can be used for hydroboration, with chemoselectivity dictated solely by the presence or absence of visible light.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yuan-Yuan Xu, Zhong-Hua Gao, Cao-Bo Li, Song Ye
Summary: The enantioselective alpha-oxidative coupling of enals with carboxylic acids was achieved by umpolung of an NHC-bound enolate with an iodine(III) reagent. The reaction produced alpha-acyloxyl-beta,gamma-unsaturated esters in good yields, with high regio- and enantioselectivities. The reaction involved the formation of an enol iodine(III) intermediate from the enolate with iodosobenzene, which changed the polarity of the enal's alpha-carbon from nucleophilic to electrophilic and facilitated the subsequent carboxylate addition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Qian Li, Yan Liu, Can Li
Summary: A synergistic ternary achiral picolinaldehyde-Zn(II)-chiral palladium complex system was reported for the highly enantioselective α-allylation of N-unprotected amino esters. By using a variety of substrates, α-allyl α-amino esters were obtained in high yields (up to 96%) with high enantioselectivities (up to 98% ee). Control experiments indicated that the coordination of Zn(II) with the Schiff base intermediate enhanced the acidity of the α-C-H bonds of amino esters, promoting α-allylation over intrinsic N-allylation. Furthermore, NMR studies revealed an interaction between the chiral palladium complex and the Zn(II)-Schiff base intermediate, resulting in the formation of a picolinaldehyde-Zn(II)-Pd(0) catalytic system.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Callum R. Woof, Derek J. Durand, Natalie Fey, Emma Richards, Ruth L. Webster
Summary: The catalytic mechanism of iron-catalyzed alkene isomerization reaction was studied through a combination of experimental and theoretical approaches. The results suggest that the isomerization of alkenes can be achieved through the combination of a hydride source and an iron(II) beta-diketiminate pre-catalyst.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Oncology
Hao Luo, Kensuke Nishi, Shuhei Ishikura, Anthony Swain, Naoyuki Morishige, Ryo Yazaki, Takashi Ohshima, Senji Shirasawa, Toshiyuki Tsunoda
ANTICANCER RESEARCH
(2018)
Article
Chemistry, Multidisciplinary
Yohei Matsumoto, Daiki Nakatake, Ryo Yazaki, Takashi Ohshima
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Organic
Takafumi Tanaka, Tsukushi Tanaka, Taro Tsuji, Ryo Yazaki, Takashi Ohshima
Article
Chemistry, Physical
Tsukushi Tanaka, Kayoko Hashiguchi, Takafumi Tanaka, Ryo Yazaki, Takashi Ohshima
Article
Chemistry, Organic
Yohei Matsumoto, Taro Tsuji, Daiki Nakatake, Ryo Yazaki, Takashi Ohshima
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Ryo Yazaki, Takashi Ohshima
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Multidisciplinary
Yohei Matsumoto, Jun Sawamura, Yumi Murata, Takashi Nishikata, Ryo Yazaki, Takashi Ohshima
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Organic
Taro Tsuji, Takafumi Tanaka, Tsukushi Tanaka, Ryo Yazaki, Takashi Ohshima
Review
Chemistry, Medicinal
Ryo Yazaki
Summary: The described catalytic chemoselective reactions enable selective activation of less reactive functionalities over more reactive ones, allowing for efficient synthesis of complex molecules without the need for tedious protection-deprotection processes. This offers new opportunities for innovative drug discovery research by expanding the chemical space available for exploration.
CHEMICAL & PHARMACEUTICAL BULLETIN
(2021)
Article
Chemistry, Organic
Tetsu Ikeda, Haruka Ochiishi, Mana Yoshida, Ryo Yazaki, Takashi Ohshima
Summary: This method involves the synthesis of a highly congested alpha,beta-dehydroamino acid through the beta-C-H bond activation of an amino acid Schiff base, with the use of abundant hydrocarbon feedstock as an alkylating reagent. The resulting alpha,beta-dehydroamino acid bears a quaternary carbon at the gamma-position with an exclusively (Z)-geometry. Additionally, a tetrasubstituted olefin can be constructed from saturated starting materials, and the synthesis also allows for the transformation into unnatural alpha-amino acid derivatives.
Article
Oncology
Kazumasa Yoshida, Kensuke Nishi, Shuhei Ishikura, Kazuhiko Nakabayashi, Ryo Yazaki, Takashi Ohshima, Masahiko Suenaga, Senji Shirasawa, Tosiyuki Tsunoda
Summary: The study discovered that NPD10621 and its derivatives can selectively suppress the growth of cancer spheroids with mutant KRAS. Among these derivatives, PMC showed the most effective inhibition of mutant KRAS spheroid growth with the least toxicity. Furthermore, PMC was able to suppress the growth of various cancer cell lines, indicating its context-independent role in cancer growth.
ANTICANCER RESEARCH
(2022)
Article
Oncology
Kazumasa Yoshida, Kensuke Nishi, Shuhei Ishikura, Taichi Matsumoto, Kazuhiko Nakabayashi, Ryo Yazaki, Takashi Ohshima, Masahiko Suenaga, Senji Shirasawa, Toshiyuki Tsunoda
Summary: In this study, RNA-seq analyses were conducted to investigate the mechanism of PMC against human colorectal cancer cells with mtKRAS. The results showed that PMC suppresses the aerobic glycolysis pathway through down-regulation of the HIF1 pathway, leading to the inhibition of cancer growth.
ANTICANCER RESEARCH
(2023)
Review
Chemistry, Organic
Tsukushi Tanaka, Ryo Yazaki, Takashi Ohshima
Summary: Enolization of carboxylic acid derivatives is a challenging task due to the low acidity of alpha-protons, requiring strong bases for efficient activation. Recent developments in catalytic methods have shown potential for chemoselective activation of carboxylic acids through a radical process, allowing for concise synthesis of diverse unnatural derivatives.
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2021)
Meeting Abstract
Chemistry, Multidisciplinary
Daiki Nakatake, Yohei Matsumoto, Ryo Yazaki, Takashi Ohshima
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2018)