Review
Chemistry, Physical
Alemayehu Gashaw Woldegiorgis, Zhao Han, Xufeng Lin
Summary: This review covers the progress achieved in chiral phosphoric acid (CPA)-catalyzed organic reactions, highlighting its versatility in various reaction types and the synthesis of enantioselective organic products of importance in biological and pharmaceutical chemistry.
JOURNAL OF MOLECULAR STRUCTURE
(2024)
Article
Chemistry, Multidisciplinary
Lisa Goclik, Henrik Walschus, Alexis Bordet, Walter Leitner
Summary: A versatile synthetic pathway has been developed for the production of valuable alkyl phenols and anilines. The immobilized bimetallic iron ruthenium nanoparticles on an imidazolium-based supported ionic liquid phase (Fe25Ru75@SILP) serve as highly active and selective catalysts for the deoxygenation of the side-chain without hydrogenation of the aromatic ring. The catalytic system allows operation under continuous flow conditions with high robustness and flexibility.
Article
Chemistry, Physical
Ryoya Tajima, Takaaki Saito, Takayoshi Arai
Summary: The conventional acid-catalyzed aza-Friedel-Crafts reaction of phenols with imines typically shows ortho-selectivity. However, a chiral bis(imidazolidine) pyridine (PyBidine)-Ni(OAc)(2) catalyst can switch the regioselectivity to para-selectivity. This switch is facilitated by the bulky PyBidine-Ni(OAc)(2) catalyst with a Ph2CHCH2 substituent, resulting in highly para-selective aza-Friedel-Crafts reactions (up to 99:1 para/ortho selectivity).
Article
Chemistry, Organic
Amjad Ali, Raveena Jajoria, Harish K. Harit, Ravi P. Singh
Summary: In this study, the addition of alpha-ketoamide top-quinone methide initiated by dialkylphosphite in the presence of organic base DBU was explored. The coupling of dialkylphosphites to alpha-ketoamides followed[1,2]-phospha-Brook rearrangement, generating alpha-phosphonyloxy enolates that were subsequently seized by p-quinonemethides. This two-step one-pot 1,6-conjugate addition method provides effective access to a series of isatin-incorporated phosphate-bearing 1,6-adducts with high yield and selectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Medicinal
Tetsuhiro Nemoto
Summary: In order to develop dearomatization reactions, selective promotion of ipso-Friedel-Crafts-type C-alkylation over competitive O- or N-alkylation reactions is essential. Our group has successfully developed various transition-metal-catalyzed dearomatization reactions using appropriately designed aromatic substrates, resulting in a wide variety of dearomatized products in a highly chemoselective manner.
CHEMICAL & PHARMACEUTICAL BULLETIN
(2023)
Article
Chemistry, Analytical
Ruizhi Tang, Jiahua Zhou, Xiaowei Li, Yang Yu, Shujuan Ma, Junjie Ou
Summary: A novel phosphonate functionalized polythiophene microsphere was designed and fabricated via Friedel-Crafts reaction, with high adsorption capacity. The microsphere was successfully used for specific capture of phosphopeptides, identifying multiple phosphopeptides from phosphoproteins.
ANALYTICA CHIMICA ACTA
(2022)
Article
Chemistry, Inorganic & Nuclear
Amir Yeganeh-Salman, Iris Elser, Karlee L. Bamford, Daniel Ebanks, Douglas W. Stephan
Summary: In this study, a catalytic conversion of B-X to B-H bond was achieved using a small amount of [Ph3C](+) as an initiator with Et3SiH. This method was successfully applied to six haloboranes. Additionally, C-F bond activation of benzyl fluorides was observed in the presence of arenes, leading to the formation of Friedel-Crafts products using B-H-9-BBN in the presence of Et3SiH. The protocol provides a simple, cost-effective, and mild route to 1,1-diarylmethanes from benzyl fluorides with high yields (up to 99%).
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Hui Liu, Yingkun Yan, Min Li, Xiaomei Zhang
Summary: By utilizing chiral phosphoric acid as a catalyst, enantioselective aza-Friedel-Crafts reaction between 5-aminoisoxazoles and isatin-derived N-Boc ketimines was achieved, yielding novel 3-isoxazole 3-amino-oxindoles with high yields and moderate to good enantioselectivities. One product's absolute configuration was determined by X-ray crystal structural analysis, and a plausible reaction mechanism was proposed, followed by a successful scale-up reaction. Additionally, the product underwent Suzuki-Miyaura coupling with phenylboronic acid, resulting in moderate yield without affecting the enantioselectivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Dingsheng Zhu, Shuai Fang, Lu Tong, Ye Lei, Guangcheng Wu, Tayba Chudhary, Hao Li
Summary: In this study, a cylinder-shaped macrocycle was successfully synthesized using Friedel-Crafts reaction with a mixture of TFB and acetone, yielding 36%. The structure of the macrocycle was confirmed using various analytical techniques, and it was found to be capable of recognizing different cationic guests through cation-dipole and CH-pi interactions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Kazutoshi Nishimura, Shibo Xu, Yuji Nishii, Koji Hirano
Summary: A metal-free, phosphenium-dication-mediated sequential C-P and C-C bond forming reaction has been developed for the concise synthesis of (di)benzophosphole derivatives from readily available and simple arylalkynes and phosphinic acids. The application of this protocol to multiple cyclization reactions and fully intermolecular three-component coupling-type reactions is also described.
Article
Chemistry, Applied
Shiyuan Zhou, Qi Lin, Zhongfei Ren, Congsheng Zhou, Yuhua Shan, Ping Liu
Summary: A series of one-step 3D structured phenyl-based hyper-crosslinked porous polymers, POP-TB, were successfully synthesized in this study. The POP-TB showed excellent adsorption performance towards four organic dyes, with maximum adsorption capacities surpassing most of the adsorbents reported previously.
MICROPOROUS AND MESOPOROUS MATERIALS
(2023)
Article
Chemistry, Applied
Huimiao Zhang, Patrick H. Toy
Summary: A halogen bond donor based on a 2,2'-bipyridine framework has been synthesized and used to catalyze Friedel-Crafts reactions of furans, yielding good reaction yields with moderate catalyst loading at low temperatures. The catalyst design allows for the potential development of an enantioselective version for stereo-selective catalysis.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Jianguo Yang, Saimei Liu, Jing Gui, Daokai Xiong, Jinshan Li, Zhiming Wang, Jun Ren
Summary: A highly selective hydroxyalkylation of aniline derivatives with arylglyoxal hydrates has been achieved using HFIP as a catalyst. The reaction provides efficient synthesis of various N,N-dialkylanilines and their derivatives with alpha-hydroxy carbonyl units under mild conditions. The method has shown great synthetic potential by enabling the facile synthesis of several structurally interesting molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Han K. Chau, Daniel E. Resasco, Phuong Do, Steven P. Crossley
Summary: The Friedel-Crafts acylation of phenolic compounds with carboxylic acids catalyzed by Bronsted-acid zeolites is an interesting reaction with potential applications in renewable fuels and chemicals production. The study evaluated the reaction under varying conditions over H-ZSM-5 catalysts, revealing that in diffusion-limited conditions, the kinetics of the reaction are significantly influenced.
JOURNAL OF CATALYSIS
(2022)
Article
Polymer Science
Hongxing Wei, Wenjing Wang, Xiangyun Xie, Zhe Shu, Zhuan Yi, Congjie Gao
Summary: We prepared solvent-resistant mixed matrix membranes (MMMs) using FeCl3 catalyzed cross-linking, which differed from previous methods and enabled superior resistance to strongly polar organic solvents. The incorporation of MOFs crystals in MMMs resulted in high permeability membranes and regulated the pore size and rejection performance. The study provides a facile method to fabricate robust solvent-resistant membranes.
