Article
Chemistry, Organic
Meng-Yang Chang, Chun-Yi Lin, Shin-Mei Chen
Summary: A high-yield, open-vessel route for the facile-operational, gram-scale synthesis of functionalized triarylmethanes (TRAMs) is described via silica-coated magnetic nanoparticles of modified polyphosphoric acid (NiFe2O4@SiO2-PPA)-mediated intermolecular Friedel-Crafts reaction of substituted aryl aldehydes with 2 equivalents of oxygenated arenes under environmentally friendly reaction conditions. Only water was generated as the by-product throughout the reaction process.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Baihui Zheng, Xiaotong Li, Shuyang Meng, Yifei Li, Qun Liu, Ling Pan
Summary: The development and applications of novel synthetic intermediates play a crucial role in synthetic chemistry. alpha-Amino alkyl radicals show promise as synthetic intermediates for the construction of versatile natural products and drugs. However, their applications have been limited due to the high reduction potentials of imines and further oxidation of the generated alpha-amino alkyl radicals. In this study, we demonstrate the selective generation of p-(N,N-dimethyl)benzyl equivalents from easily-available N,N-dimethyl arylamines via alpha-amino alkyl radicals in the presence of an iridium photosensitizer, without the need for any other additives. Under mild reaction conditions, a series of trifluoromethyl-containing diarylalkanes were obtained in good to high yields from the visible-light-promoted reaction of N,N-dimethyl arylamines and quinols. This route provides a novel and environmentally-friendly method for accessing trifluoromethyl-containing arenes.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Polymer Science
Mohamed Gamal Mohamed, Mei-Yin Tsai, Chih-Feng Wang, Chih-Feng Huang, Martin Danko, Lizong Dai, Tao Chen, Shiao-Wei Kuo
Summary: Two types of hybrid porous organic polymers with high surface areas and outstanding thermal stabilities were successfully synthesized. POSS-TPP showed high carbon dioxide capacity and iodine adsorption capacity compared to POSS-TPE.
Article
Chemistry, Multidisciplinary
Zhengyu Han, Yu Zang, Chang Liu, Wengang Guo, Hai Huang, Jianwei Sun
Summary: A new organocatalytic asymmetric method for the synthesis of enantioenriched triarylmethanes has been developed, which employs asymmetric reduction via C-H bond formation as the key step, without requiring the presence of a heteroaryl ring or the presynthesis of unstable para-quinone methides.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Inorganic & Nuclear
Xue-Chun Fang, Tong-Mou Geng, Feng-Qiang Wang, Wang-Hua Xu
Summary: Two nitrogen-rich conjugated microporous polymers (TEDOT and TBTh) with high stability and perpetual porosity were successfully synthesized through the Friedel-Crafts reaction. Both polymers show good fluorescence detecting abilities towards 2,4-dinitrophenol (DNP) and exhibit good iodine absorption and desorption properties.
JOURNAL OF SOLID STATE CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Baosheng Wei, Qianyi Ren, Thomas Bein, Paul Knochel
Summary: A variety of functionalized triarylmethane and 1,1-diarylalkane derivatives were successfully synthesized via a transition-metal-free, one-pot, two-step procedure, demonstrating the synthetic utility of the method for biologically relevant molecules. The sequential cross-coupling enabled by changing the solvent from THF to toluene and the proposed S(N)1-type mechanism were supported by experimental studies. The method was further demonstrated by the synthesis of several biologically relevant molecules, including an anti-tuberculosis agent, an anti-breast cancer agent, a precursor of a sphingosine-1-phosphate (S1P) receptor modulator, and a FLAP inhibitor.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Materials Science, Multidisciplinary
Tong-Mou Geng, Xue-Chun Fang, Feng-Qiang Wang, Feng Zhu
Summary: A multifunctional thiophene-based covalent triazine framework (TTPATTh) with triphenylamine as core is synthesized for the first time by Friedel-Crafts reaction, showing high yield and thermal stability. TTPATTh and TTPATCz have high BET surface areas and pore volumes.
MACROMOLECULAR MATERIALS AND ENGINEERING
(2021)
Article
Chemistry, Organic
Dwaipayan Das, Agniva Das, Saiful Islam, Asish R. R. Das, Adrita Banerjee, Romit Majumder, Debasish Bandyopadhyay
Summary: An efficient and intriguing method using Rh(II) catalysis has been developed for the preparation of fused furan moieties. The technique involves a one-pot C-H activation/concomitant tandem annulation process using an enolic compound and a beta-keto sulfoxonium ylide as reactants. The synthesis only requires Rh-2(TFA)(4) as the catalyst, removing the need for additional metallic or nonmetallic additives. This transformation of naphthoquinone fused furan into highly decorated naphthoquinone fused indolizines shows great promise in synthetic applications.
Article
Chemistry, Organic
Takanori Shibata, Mio Sasaki, Masafumi Kojima, Mamoru Ito
Summary: The chiral Ir(I)-catalyzed intermolecular reaction of N-carbamoylpyrrole and indole derivatives with alpha,beta-unsaturated carbonyl compounds proceeded with high enantioselectivity, yielding chirally functionalized pyrroles and indoles as formal C-H conjugate adducts. The reaction mechanism was further investigated through deuterium labeling experiments.
Article
Chemistry, Organic
Suttida Rinkam, Warapong Senapak, Sarayut Watchasit, Rungnapha Saeeng, Uthaiwan Sirion
Summary: A convenient and practical method for the synthesis of unsymmetrical triarylmethanes was demonstrated using a Bronsted acidic ionic liquid as the catalyst in a one-pot three-component double Friedel-Crafts reaction at 80 degrees C. The reaction was successful under metal- and solvent-free conditions, yielding moderate to high yields of the desired products from a wide range of substrates. The mechanism of the reaction was studied using quantitative NMR analysis.
Article
Chemistry, Organic
Jodie L. Hann, Catherine L. Lyall, Gabriele Kociok-Kohn, Simon E. Lewis
Summary: This study presents a method for the synthesis of N-alkoxycarbonyl pyrroles by the condensation of readily available O-substituted carbamates with 2,5-dimethoxytetrahydrofuran. It is demonstrated that N-alkoxycarbonyl protection can impart distinct reactivity to pyrrole in comparison with N-sulfonyl protection.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Materials Science, Multidisciplinary
Na Liu, Jienan Chen, Zhiping Wu, Peng Zhan, Lin Zhang, Quan Wei, Fen Wang, Lishu Shao
Summary: This study developed a series of microporous lignin-based hypercross-linked polymers with excellent iodine adsorption capacity and reusability, utilizing organosolv lignin extracted from poplar sawdust. These lignin-based polymers offer a promising solution for environmental remediation by providing efficient adsorbents.
ACS APPLIED POLYMER MATERIALS
(2021)
Article
Chemistry, Multidisciplinary
Fengzhe Guo, Jing Xiao, Jinfeng Deng, Fangshao Li, Zi-Long Tang
Summary: An efficient PCl3-promoted Friedel-Crafts reaction using esters as both alkylating and acylating reagents has been developed. This novel strategy features high step economy, low-cost, metal-free, and simple reaction conditions.
Article
Chemistry, Multidisciplinary
Fengzhe Guo, Jing Xiao, Jinfeng Deng, Fangshao Li, Zi-Long Tang
Summary: An efficient PCl3-promoted Friedel-Crafts reaction using esters as both alkylating and acylating reagents has been developed, producing aromatic ketones and alkyl aromatics in good yields in one step. This novel strategy features high step economy, low-cost, metal-free, and simple reaction conditions.
Article
Chemistry, Multidisciplinary
Ali Enis Sadak, Evren Cucu, Beyza Hamur, Ilker Un, Ramazan Altundas
Summary: The most important factor in synthesizing a hyper-crosslinked polymer with high CO2 adsorption and selectivity is the choice of compatible core and linker. In this study, EBE-06, a microporous hyper-crosslinked conjugated polymer, was successfully synthesized and showed excellent gas adsorption and selectivity properties, making it a promising candidate for CCUS processes.
JOURNAL OF CO2 UTILIZATION
(2023)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
