Article
Chemistry, Organic
Tanumay Roy, Krishanu Mondal, Arunava Sengupta, Parthasarathi Das
Summary: An efficient N-arylation reaction of hydantoins with substituted aryl/heteroaryl boronic acids has been developed using CuF2/MeOH as the catalyst under base and ligand-free conditions at room temperature and open air. The reaction is general and provides excellent yields of various N-arylated hydantoins with exclusive regioselectivity. The study also explores the selective N3-arylation of nucleosides and demonstrates the gram-scale synthesis of the drug Nilutamide. A mechanistic study reveals the importance of hydantoin and MeOH in the generation of catalytically active copper species, and the proposed reaction mechanism suggests the favorable N3-arylation of hydantoin in MeOH due to the formation of a square-planar Cu(II) complex with strong hydrogen-bond interactions. This research provides valuable insights into Cu(II)-catalyzed oxidative N-arylation reactions and has implications for the design and development of Cu-catalyzed coupling reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Jing-Jing Tang, Xiaoqiang Yu, Yoshinori Yamamoto, Ming Bao
Summary: A visible-light-promoted and simple iron salt-catalyzed N-arylation was efficiently achieved under external photosensitizer-free conditions. The method features high reactivity, wide substrate scope, and good functional group tolerance.
Article
Chemistry, Multidisciplinary
Nanxing Gao, Yanshun Li, Guorui Cao, Dawei Teng
Summary: The cross-electrophile coupling of aryl bromides and cyclic secondary alkyl bromides catalyzed by nickel/spiro-bidentate-pyox ligands with lithium chloride as the additive for Csp(2)-Csp(3) bond formation was reported. Various aryl-cyclic secondary alkyl Csp(2)-Csp(3) bond products were successfully synthesized under optimal reaction conditions.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Daniel Sowa Prendes, Florian Papp, Nagesh Sankaran, Nardana Sivendran, Frederike Beyer, Christian Merten, Lukas J. Goossen
Summary: Arylglycines, which are important pharmacophores in several top-selling drugs, can now be synthesized from abundant aryl chlorides using a Pd-catalyzed Schollkopf-type amino acid synthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Gonglin Li, Yan Zhang, Hongkun Zeng, Xiaoming Feng, Zhishan Su, Lili Lin
Summary: In this study, a novel asymmetric catalytic reaction was reported, in which the diastereoselectivity of the substrates was controlled by using a bispidine-based chiral amine catalyst and water. The resulting products showed potential anti-HIV-1 activity, with high yields and ee values. Control experiments and theoretical calculations revealed the diastereodivergent mechanism of the reaction, providing inspiration for further studies on diastereodivergent asymmetric synthesis.
Article
Chemistry, Organic
Wangyu Li, Dungai Wang, Xiao Liang, Zhixiong Jin, Shiwen Zhou, Guanru Chen, Yuanjiang Pan
Summary: A Lewis acid-catalyzed selective reaction for the synthesis of diarylmethanes or oxoimidazolidines from anilines and glyoxylates was developed. The reaction yielded a series of aniline-based diarylmethanes and stereoselective oxoimidazolidines, depending on the catalyst used.
Article
Chemistry, Inorganic & Nuclear
Dian Wang, Chase A. Salazar, Shannon S. Stahl
Summary: This study reveals the importance of catalyst-controlled regioselectivity in Pd-catalyzed C-H arylation of heteroarenes, showing that the addition of specific ancillary ligands can switch the regioselectivity from C2 to C3. This switch in selectivity is attributed to a change in the reaction mechanism, from a C2-selective oxidative-Heck pathway to a C3-selective C-H activation/reductive elimination pathway, as supported by density functional theory calculations.
Article
Chemistry, Multidisciplinary
Mixiang Tian, Lidong Shao, Xiaosan Su, Xuhong Zhou, Honglei Zhang, Kun Wei, Ruifen Sun, Junliang Wang
Summary: A new method has been developed for selective oxygenation of benzaldehydes and benzylic amines at the ortho positions to prepare fluoroalkyl aryl ethers.
Article
Chemistry, Organic
Li Zhang
Summary: A modular and straightforward synthetic strategy has been developed for the preparation of alpha-substituted alkenyl acetals. The protocol shows good to high yields in the Pd-catalyzed Suzuki cross-coupling of alpha-haloalkenyl acetals with (het)aryl boronic acids, aryl boronates, or B-alkyl-9-borabicyclo[3.3.1]nonanes under mild conditions. This method features broad substrate scope, good functional-group compatibility, and scalability.
Article
Chemistry, Multidisciplinary
Luis angel Turcio-Garcia, Hugo Valdes, Simon Hernandez-Ortega, Daniel Canseco-Gonzalez, David Morales-Morales
Summary: The synthesis and characterization of twelve Rh(i) complexes with fluorinated NHC ligands were described. The catalytic activity of these complexes in the arylation of aldehydes was found to be related to the number of fluorine atoms present in their structures. More fluorine atoms in the NHC ligand led to higher catalytic activity, likely due to the reduced electron-donating properties of the ligand.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Guoqiang An, Limin Wang, Jianwei Han
Summary: This method developed by using palladium-catalyzed C-2-arylation/intramolecular acylation with arylcarboxylic acids using diaryliodonium salts has the advantage of good step-economy by two chemical bonds formation in one pot.
Article
Chemistry, Organic
Xue-Qing Mou, Min Wang, Liang-Chen Ren, Yu-Rui Jian, Xin-Yu Fu, Hong-Yu Zheng, Xiao Zha, Bao-Dong Cui, Yun Zhang, Yong-Zheng Chen
Summary: A general photoredox-catalyzed intramolecular oxy- and aminoacylation of internal alkenes with acyl oxime esters to access various acyl heterocycles is developed.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Xuan Jiang, Hao Jiang, Qian Yang, Ying Cheng, Liang-Qiu Lu, Jon A. Tunge, Wen-Jing Xiao
Summary: Grignard addition is an important method for synthesizing alcohol compounds, and the cobalt-catalyzed asymmetric reductive Grignard-type addition allows for the synthesis of chiral benzyl alcohols. This method has the advantages of mild reaction conditions, good functionality tolerance, and excellent enantiocontrol.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Taiga Yurino, Sunaho Saito, Mizuki Ichihashi, Takeshi Ohkuma
Summary: A Pd(OAc)(2)/P(OPh)(3) combination catalyst was used for the Tsuji-Trost-type allylic amination under aerobic conditions, and it was found that the reaction proceeded efficiently only when allylic phosphates were employed as electrophiles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Letter
Chemistry, Organic
Kento Yasumoto, Noritaka Kunitomo, Taichi Kano
Summary: The Cu-catalyzed asymmetric conjugate addition of trialkenylboroxines to enone diesters is described. This operationally simple and scalable reaction proceeds at room temperature and tolerates a wide range of substrates. The practical utility of this method is demonstrated through the formal synthesis of (+)-methylenolactocin. Mechanistic studies reveal the synergistic action of two different catalytic species.
Article
Chemistry, Organic
Masami Kuriyama, Kosuke Yamamoto, Keiko Ishimaru, Noriyuki Fujimura, Daishiro Minato, Osamu Onomura
Article
Pharmacology & Pharmacy
R. Shimazawa, M. Ikeda
JOURNAL OF CLINICAL PHARMACY AND THERAPEUTICS
(2018)
Article
Chemistry, Applied
Yohei Matsumoto, Masami Kuriyama, Kosuke Yamamoto, Koyo Nishida, Osamu Onomura
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2018)
Article
Chemistry, Applied
Kosuke Yamamoto, Shota Ishimaru, Tatsuya Oyama, Satoko Tanigawa, Masami Kuriyama, Osamu Onomura
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2019)
Article
Chemistry, Organic
Yohei Matsumoto, Kosuke Yamamoto, Masami Kuriyama, Koyo Nishida, Osamu Onomura
SYNTHESIS-STUTTGART
(2019)
Article
Electrochemistry
Kosuke Yamamoto, Naoto Kikuchi, Tohru Hamamizu, Hirofumi Yoshimatsu, Masami Kuriyama, Yosuke Demizu, Osamu Onomura
Article
Chemistry, Organic
Kosuke Yamamoto, Keiko Ishimaru, Satoshi Mizuta, Daishirou Minato, Masami Kuriyama, Osamu Onomura
Article
Chemistry, Applied
Masami Kuriyama, Gemba Yano, Hirotoshi Kiba, Tetsuro Morimoto, Kosuke Yamamoto, Yosuke Demizu, Osamu Onomura
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2019)
Review
Chemistry, Multidisciplinary
Kosuke Yamamoto, Masami Kuriyama, Osamu Onomura
ACCOUNTS OF CHEMICAL RESEARCH
(2020)
Article
Pharmacology & Pharmacy
Rumiko Shimazawa, Masayuki Ikeda
Summary: This study found that different regulatory authorities made different decisions regarding the safety and efficacy of hypoglycemic drugs based on identical trial data. The differences in the wording of initial indications between Japan and other authorities suggest different interpretations of trial data and T2D in these regions.
BRITISH JOURNAL OF CLINICAL PHARMACOLOGY
(2021)
Article
Chemistry, Organic
Kasumi Mastuo, Masami Kuriyama, Kosuke Yamamoto, Yosuke Demizu, Koyo Nishida, Osamu Onomura
Summary: Nickel-catalyzed hydrodeoxygenation of aryl sulfamates can be achieved using alcohols as mild reductants, resulting in high yields of desired products with tolerance to various functional groups and heterocycles. Additionally, gram-scale production and stepwise cine-substitution were efficiently carried out in this reaction system.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Masami Kuriyama, Natsumi Hanazawa, Yusuke Abe, Kotone Katagiri, Shimpei Ono, Kosuke Yamamoto, Osamu Onomura
Review
Medicine, General & Internal
Masayuki Ikeda, Rumiko Shimazawa
JOURNAL OF GENERAL AND FAMILY MEDICINE
(2019)
Article
Pharmacology & Pharmacy
Rumiko Shimazawa, Yoshinobu Kano, Masayuki Ikeda
PHARMACOLOGY RESEARCH & PERSPECTIVES
(2018)
Article
Chemistry, Organic
Masami Kuriyama, Satoshi Kamogawa, Kosuke Yamamoto, Osamu Onomura
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.
