Article
Chemistry, Organic
Fengyue Zhao, Yixuan Li, K. N. Houk, Qianqian Lu, Fang Liu
Summary: The ring-closing metathesis reaction of diene is important in cyclic compound synthesis. This research used density functional theory (DFT) calculations to understand the mechanisms and selectivity in ring-closing metathesis and homometathesis. The results showed that substrate conformation determines the selectivity. Ester-tethered substrates favor homometathesis due to the planar structure of the ester, while amide-tethered substrates only undergo ring-closing metathesis due to steric hindrance.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Pawel M. Szczepanik, Andrey A. Mikhaylov, Ondrej Hylse, Roman Kucera, Petra Dadova, Marek Necas, Lukas Kubala, Kamil Paruch, Jakub Svenda
Summary: We report a new synthetic strategy for the flexible preparation of forskolin-like molecules. Stereoselective Michael addition and ring-opening metathesis paired with ring closure were key steps in achieving the concise assembly of the tricyclic core. Late-stage functionalization sequences transformed the tricyclic intermediates into a set of different forskolin-like molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jun Zhu, Rui Zhang, Guangbin Dong
Summary: A rare reversible C-C single-bond metathesis reaction catalyzed by ruthenium was reported, enabling the synthesis of biaryl compounds under redox-neutral and pH-neutral conditions. The reaction mode involves unexpected 18-electron closed-shell intermediates and is expected to inspire the development of more general C-C single-bond metathesis and orthogonal cross-coupling reactions.
Article
Chemistry, Organic
Tuong Anh To, Binh Khanh Mai, Thanh Vinh Nguyen
Summary: This article reports a new Bronsted acid-catalyzed carbonyl-olefin metathesis reaction using nitromethane as a solvent, which can promote intramolecular ring-closing reactions.
Article
Polymer Science
Qiang Gui, Changou Pan, Siwei Shen, Pengwei Xie, Mingliang Pei, Peng Liu
Summary: Fluorination of nitrile-butadiene rubber (NBR) was efficiently achieved through olefin cross metathesis (OCM) technique using 1H,1H,2H,2H-perfluorooctyl acrylate (F13) as the model fluorinating chain transfer agent (F-CTA). The optimized conditions led to a liquid F-NBR with a fluorination degree of 1.84%, and the reaction process was elucidated based on changes in fluorination degree and molecular weight of the F-NBR products.
Article
Chemistry, Organic
Chun-Ting Chou, Chun-Wei Lu, Bing-Syuan Wu, Cheng-Che Tsai
Summary: This paper describes the study on the kinetic resolution of racemic secondary alcohols (O-nucleophiles) via stereoselective intramolecular allylic substitution. The reaction was achieved by the synergistic catalysis of palladium and chiral phosphoric acid, yielding chiral cis-1,3-disubstituted 1,3-dihydroisobenzofurans with a selective factor of up to 60.9 and a diastereomeric ratio of up to 7.8:1. The application of this methodology in the asymmetric synthesis of a compound with antihistaminic activity was demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Kenta Mori, Midori Akiyama, Ko Inada, Yutaka Imamura, Yuichiro Ishibashi, Yusuke Takahira, Kyoko Nozaki, Takashi Okazoe
Summary: By introducing a seven-membered N-heterocyclic carbene (NHC) ligand, a significant increase in catalyst turnover number (TON) was achieved in the cross-metathesis of tetrafluoro-ethylene (TFE) and vinyl ethers. This study provides a new approach to enhance catalytic efficiency in such reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Zhanchao Meng, Simon M. Spohr, Sandra Tobegen, Christophe Fares, Alois Fuerstner
Summary: The synthesis of polycyclic marine alkaloids involves diverse reaction pathways and catalysts. The combination of RCAM and macrolactamization is particularly significant in this process.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Polymer Science
Janis V. Musso, Paul Gebel, Vincent Gramm, Wolfgang Frey, Michael R. Buchmeiser
Summary: A system for visible-light-controlled ring-opening metathesis polymerization (ROMP) was developed by combining thermally latent group 6 olefin metathesis initiators with a photoredox catalyst. This system can be applied to two-dimensional (2D) photolithography, and it exhibits high activity and stability without the need for thermal or UV post-curing.
Article
Chemistry, Physical
Leonildo A. Ferreira, Josiane T. Silva, Raissa G. Alves, Kelley C. B. Oliveira, Eduardo N. dos Santos
Summary: In this study, the cross metathesis of estragole and methyl sorbate was investigated to produce methyl 6-(4-methoxyphenyl)hexa-2,4-dienoate with good conversion and selectivity using ruthenium-based metathesis catalysts at low catalyst loadings as 50 ppm (0.005 mol%) and minimal solvent. This demonstrates the importance of catalyst selection and reaction conditions in achieving the desired product conversion and selectivity.
APPLIED CATALYSIS A-GENERAL
(2021)
Article
Chemistry, Applied
Haifeng Yu, Jian Mo, Xuemin Niu, Dashuang Luo, Guangbo Che
Summary: Switchable synthesis of 3-alkenyl succinimides and maleimides was achieved by adjusting reaction conditions. The Michael addition reaction of alpha-oxo ketene dithioacetals and maleimides using CH3SO3H in DCE at 120 degrees C resulted in 40-90% yields of 3-alkenyl succinimides. The oxidative cross-coupling reaction of alpha-oxo ketene dithioacetals with maleimides using Pd(OAc)(2) in DMF at 20 degrees C yielded 40-80% yields of 3-alkenyl maleimides. The method can be scaled up to gram scale without the need for directing groups on the substrates.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Tynchtyk Amatov, Nobuya Tsuji, Rajat Maji, Lucas Schreyer, Hui Zhou, Markus Leutzsch, Benjamin List
Summary: This study reports two highly enantioselective and diastereoselective catalytic Mukaiyama aldol reactions, which directly deliver valuable silyl protected propionaldehyde aldols with control over stereochemistry. A single atom modification in the catalyst core leads to a dramatic switch in enantioselectivity of the aldehyde through unconventional C-H hydrogen bonding interactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Stella A. Gonsales, Zoe C. Mueller, Fengyue Zhao, Paulo H. S. Paioti, Lydia Karmazin, Jing Wan, Fang Liu, K. N. Houk, Amir H. Hoveyda
Summary: The study reveals that phosphine-free Ru-CAAC complexes have the steric and electronic attributes to be highly effective in generating allenes, paving the way for the development of additional olefin metathesis reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Yucheng Mu, Felix W. W. Hartrampf, Elsie C. Yu, Katherine E. Lounsbury, Richard R. Schrock, Filippo Romiti, Amir H. Hoveyda
Summary: This study introduces a new method for synthesizing trisubstituted macrocyclic olefins, which can produce stereoisomers and overcome unexpected difficulties. The effectiveness of the method is demonstrated through two examples.
Article
Chemistry, Inorganic & Nuclear
Jordan De Jesus Silva, Margherita Pucino, Feng Zhai, Deni Mance, Zachariah J. Berkson, Darryl F. Nater, Amir H. Hoveyda, Christophe Coperet, Richard R. Schrock
Summary: In this study, the catalytic performances of molybdenum oxo alkylidene species with different anionic O ligands were evaluated in metathesis reactions of internal and terminal olefins. It was found that the presence of the ORF9 ligand significantly increased catalytic activity, particularly in the molecular form. In contrast, molecular complexes with large aryloxy anionic ligands showed little activity, while their silica-supported counterparts exhibited improved activity.
INORGANIC CHEMISTRY
(2021)
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)