Article
Chemistry, Applied
Ravindra S. Phatake, Noy B. Nechmad, Ofer Reany, N. Gabriel Lemcoff
Summary: A selective ring-closing metathesis (RCM) reaction using latent sulfur chelated ruthenium iodide benzylidenes as catalysts, activated by thermal and photochemical stimuli, has been reported. This method enables the formation of large macrocycles with high yields, especially for dienes with one terminal alkene and one internal double bond. For substrates containing two internal double bonds, a sacrificial methylene donor can be used to obtain the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Plant Sciences
Jiahui Lin, Zihao Zhu, Yuwen Chen, Weiwei Zuo, Meifang Zhu, Zhiyuan Ma
Summary: The combination of ring-closing metathesis with betulin allows for the synthesis of a library of triterpenoid derivatives for potential pharmacological research. Different types of betulin derivatives were prepared by coupling reactions and subsequent ring-closing metathesis. The resulting betulin-based olefin derivatives showed potential applications in the biomedical field.
JOURNAL OF NATURAL PRODUCTS
(2023)
Review
Chemistry, Physical
Augustin Nouaille, Jan Lorkowski, Xavier Pannecoucke, Marc Mauduit, Thomas Poisson, Samuel Couve-Bonnaire
Summary: This article presents a review of the challenges in using fluoroalkenes in ring-closing metathesis and cross-metathesis, highlighting the major developments in this field in recent years.
Article
Chemistry, Organic
Atsushi Ueda, Yui Makura, Sana Kakazu, Takuma Kato, Tomohiro Umeno, Kazuhiro Hirayama, Mitsunobu Doi, Makoto Oba, Masakazu Tanaka
Summary: In this study, a selective E-type ring-closing metathesis reaction was discovered in α-helical stapled peptides. By using chiral carbocyclic α,α-disubstituted α-amino acids, a high E-selectivity was achieved, while standard acyclic amino acids resulted in lower selectivity. The stapled octapeptide exhibited a right-handed α-helical crystal structure.
Article
Chemistry, Multidisciplinary
Anas Semghouli, Attila M. Remete, Lorand Kiss
Summary: Novel functionalized fused-ring β-amino lactones and lactams with multiple chiral centers were synthesized from readily available strained bicyclic β-amino acids via a stereocontrolled synthetic route. The key step involved ring-rearrangement metathesis of allyl/propargyl esters or N-allylated/N-propargylated amides of (oxa)norbornene β-amino acids. The RRM transformations were investigated using commercially available catalysts. Importantly, the procedure did not alter the configurations of the chiral centers, meaning that the starting (oxa)norbornene β-amino acids predetermined the configuration of the formed products.
Article
Chemistry, Multidisciplinary
Nils Ansmann, Thaddaus Thorwart, Lutz Greb
Summary: The Lewis superacid bis(perchlorocatecholato)silane catalyzes C-O bond metathesis of alkyl ethers with high efficiency, enabling chemoselective ring contractions of macrocyclic crown ethers and unprecedented ring-closing metathesis of polyethylene glycols for polymer-selective degradation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Organic
Santhosh Kumar Podiyanachari, Hassan S. Bazzi, Mohammed Al-Hashimi
Summary: Synthesis of cycloolefin-based polymers via metathesis-accompanied cyclopolymerization and tandem ring-opening/ring-closing metathesis (RO/RCM) polymerization leads to highly functional cycloolefin ring-based polymers.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Felix Ziegler, Thomas Roider, Markus Pyschik, Christian P. Haas, Dongren Wang, Ulrich Tallarek, Michael R. Buchmeiser
Summary: The study demonstrates the efficient use of a 2(nd)-generation Hoveyda-Grubbs-type catalyst immobilized inside mesoporous silica for selective macro(mono)cyclization (MMC) of an alpha,omega-diene under spatially confined and continuous-flow conditions. By analyzing reaction mixtures through NMR and MALDI-TOF-MS, the study identifies the effects of confinement on olefin metathesis pathways and determines conditions for achieving high MMC selectivity. The research also highlights the preference for ring-closing metathesis of monomers and backbiting from dimers and trimers under confinement, leading to a high MMC selectivity of 60%.
Article
Chemistry, Multidisciplinary
Adrian Sytniczuk, Mariusz Milewski, Michal Dabrowski, Karol Grela, Anna Kajetanowicz
Summary: A set of macrocyclic unsaturated musk compounds were obtained through a high-concentration RCM process, achieved by forming oligomers and then undergoing backbiting metathesis reaction. The process exhibited high selectivity and yielded pure macrocyclic musk products. The reaction conditions were user-friendly and environmentally friendly, using commercially available catalyst and bio-sourced oleic acid substrates.
Article
Multidisciplinary Sciences
Shiran Aharon, Dan Meyerstein, Eyal Tzur, Dror Shamir, Yael Albo, Ariela Burg
Summary: This study developed a single-stage process for the entrapment of ruthenium-based catalysts using the sol-gel process, with results showing that the nature of the precursor affects pore size and catalyst activity, and matrices prepared with tetraethoxysilane at an alkaline pH exhibit a better reaction rate. This research is the first to present a one-step process simpler and faster than methods reported in the literature for catalyst entrapment by the sol-gel process under standard conditions.
SCIENTIFIC REPORTS
(2021)
Article
Chemistry, Multidisciplinary
Saswata Gupta, Siyuan Su, Yu Zhang, Peng Liu, Donald J. Wink, Daesung Lee
Summary: Metallaaromatics are a unique class of aromatic compounds incorporating one or more transition metal elements, showing distinctive structural and theoretical interests, and serving as a novel platform for new catalyst development.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Applied
Eva Pump, Albert Poater, Naeimeh Bahri-Laleh, Raffaele Credendino, Luigi Serra, Vittorio Scarano, Luigi Cavallo
Summary: This study computationally investigates the origin of chemo-, regio- and stereoselectivity in cross metathesis reactions leading to the desired product. By comparing the relative stabilities of intermediates and products, as well as transition states, the probability for each pathway is linked. The transition states in each reaction play a crucial role in tuning the regio- and stereoselectivity by defining the energy barriers needed to form the final product. The research findings provide valuable insights for understanding the selectivity in new olefin metathesis reactions and a web-server is developed to support future predictive catalysis.
Article
Chemistry, Organic
Jennifer A. Nguyen, David C. Cabanero, Tomislav Rovis
Summary: A system for electrochemically controlling ruthenium-catalyzed olefin metathesis has been developed. This system, catalyzed by a commercially-available bis-NHC Ru complex, exhibits a wide substrate scope with short reaction times, and achieves excellent temporal control over metathesis using only electricity as a stimulus.
Article
Chemistry, Multidisciplinary
Dmitry S. Belov, Gabriela Tejeda, Charlene Tsay, Konstantin V. Bukhryakov
Summary: Vanadium-based catalysts have been demonstrated to catalyze ring-closing olefin metathesis reactions by well-defined V chloride alkylidene phosphine complexes, exhibiting good functional group tolerance. The properties of the imido group and phosphine were found to play a crucial role in the stability of active intermediates.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Ren Wei Toh, Michal Patrzalek, Tomasz Nienaltowski, Jakub Piatkowski, Anna Kajetanowicz, Jie Wu, Karol Grela
Summary: The development of continuous-flow reactors has attracted attention in the synthetic community, offering a safe and easy scaling-up alternative compared to batch reactors. By demonstrating a flow setup for ring-closing metathesis and reducing ruthenium contamination through soluble metal scavenger, the method shows potential for industrial usage. An upscale process for a Sildenafil analogue in continuous-flow fashion was achieved through adjusting tubing size and flow rate.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Inorganic & Nuclear
Hao Hu, Wei-Yi Wu, Tamotsu Takahashi, Kazuhiro Yoshida, Masamichi Ogasawara
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2017)
Review
Chemistry, Organic
Kohei Watanabe, Takashi Mino, Eri Ishikawa, Miyu Okano, Tatsuya Ikematsu, Yasushi Yoshida, Masami Sakamoto, Kazuki Sato, Kazuhiro Yoshida
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Review
Chemistry, Multidisciplinary
Kazuhiro Yoshida, Risa Yasue
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Inorganic & Nuclear
Risa Yasue, Kazuhiro Yoshida
Article
Chemistry, Organic
Yuya Miwa, Takumi Kamimura, Kiyoaki Sato, Daichi Shishido, Kazuhiro Yoshida
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Waka Takagaki, Risa Yasue, Kazuhiro Yoshida
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2020)
Article
Chemistry, Organic
Shuta Sakai, Kazuki Sato, Kazuhiro Yoshida
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Physical
Kazuhiro Yoshida, Qiang Liu, Risa Yasue, Shiro Wada, Ryosuke Kimura, Takuma Konishi, Masamichi Ogasawara
Article
Chemistry, Organic
Jun-ichi Ueda, Yuuki Enomoto, Mizuki Seki, Takuma Konishi, Masamichi Ogasawara, Kazuhiro Yoshida
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Applied
Risa Yasue, Kazuhiro Yoshida
Summary: By utilizing rhodium-catalyzed C-H bond amination, optically active amino acids containing the adamantane core were synthesized with high enantiomeric excess up to 85%. The enantioenriched products demonstrated synthetic utility as chiral building blocks, being converted into a dipeptide derivative and a Schiff-base ligand. The absolute configuration of one amino acid derivative was confirmed by X-ray single-crystal structure analysis.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Mizuki Seki, Kazuhiro Yoshida
Summary: A new chiral rhodium catalyst was synthesized and fully characterized, showing good catalytic activity and enantioselectivity in asymmetric reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Aya Saito, Kazuhiro Yoshida, Hideo Togo
Summary: Treatment of N-propargyl-N'-tosylhydrazines with molecular iodine (I-2) in the presence of NaHCO3 under warming conditions efficiently afforded the corresponding 5-substituted 4-iodo-1-tosylpyrazoles, while the same reaction in the presence of acetic acid generated the corresponding 5-aryl-4-iodopyrazoles.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Kazuki Ito, Shuta Sakai, Kazuhiro Yoshida
Summary: The reaction of 3-arylbenzo[b]thiophenes and elemental sulfur to obtain [1]benzothieno[2,3-b][1]benzothiophenes (BTBTs) is reported. The addition of molecular iodine is essential for the reaction, and it enables the formation of the desired products with high yield and purity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Risa Yasue, Masaru Miyauchi, Kazuhiro Yoshida
ADVANCED SYNTHESIS & CATALYSIS
(2017)
Article
Chemistry, Multidisciplinary
Yuta Shikata, Risa Yasue, Kazuhiro Yoshida
CHEMISTRY-A EUROPEAN JOURNAL
(2017)