Article
Chemistry, Applied
Guorong Xiao, Kaifu Wu, Wei Zhou, Qian Cai
Summary: A copper-catalyzed [3+2] cylcoaddition/ alkenyl C-N coupling tandem reaction was demonstrated, providing a method for the formation of triazolopiperidine skeletons.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Huiping Yin, Tianjiao Huang, Bai Shi, Wei Cao, Chenxia Yu, Tuanjie Li, Kai Zhang, Changsheng Yao
Summary: A practical, convenient, and facile method for constructing highly functionalized 2-pyrrolidinone has been developed using N-heterocyclic carbene (NHC)-catalyzed radical tandem cyclization (30 examples, up to 94% yield). The method is transition metal-free and exhibits broad substrate scope, excellent functional group compatibility, and high efficiency.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Guanghui Wang, Jian Jia, Gang Liu, Mingwu Yu, Xiaoxiao Chu, Xiguang Liu, Ximei Zhao
Summary: An efficient one-step synthesis of 2-acylquinolines using a copper-catalyzed tandem reaction has been developed, providing a practical tool for synthetic and pharmaceutical chemists. The method avoids multi-step operation and the use of highly toxic cyanides, with various products obtained with perfect regioselectivity in moderate to good yields. The potential synthetic utility of this method is exemplified by a large-scale experiment and synthetic transformation of the products.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Mingming Zhao, Yiming Guo, Qi Wang, Lanqi Liu, Shujie Zhang, Wei Guo, Lin-Ping Wu, Fayang G. Qiu
Summary: This paper presents an efficient synthesis of 2-iminothiazolidin-4-ones through a copper-catalyzed tandem annulation reaction involving alkyl amines, isothiocyanates, and diazo acetates. The [2 + 1 + 2] cyclization method offers advantages such as readily accessible starting materials, simplicity of operation, mild reaction conditions, high yields, step-economy, and tolerance towards diverse functional groups. Furthermore, the reaction is applicable to gram-scale synthesis and the preparation of bioactive molecules.
Article
Chemistry, Multidisciplinary
Huanqin Guan, Mengqi Shen, Cooro Harris, Honghong Lin, Kecheng Wei, Michael Morales, Noah Bronowich, Shouheng Sun
Summary: This study reports the synthesis of Cu2O nanoparticles by controlling the oxidation of Cu nanoparticles, and investigates their application as catalysts in ammonia borane dehydrogenation, nitroarene hydrogenation, and amine/aldehyde condensation reactions. The 13 nm Cu2O nanoparticles show high catalytic activity in converting nitro groups to amines, and facilitate the synthesis of highly stable PBO materials.
Article
Chemistry, Physical
Feng Zhong, Wen-Jun Yue, Xing-Hao Yin, Hong-Ming Zhang, Liang Yin
Summary: A copper(I)-catalyzed alkynylogous Mannich-type reaction is developed to provide chiral alpha-allenylamine derivatives in high selectivities. Additionally, a copper(I)-catalyzed cascade cyclization yields chiral beta-lactams containing a pyrazole moiety in high enantioselectivity. The synthetic utility and versatility of the alkynylogous product are demonstrated.
Article
Biochemistry & Molecular Biology
Itaru Nakamura, Mai Tachibana, Riku Konta, Hiroki Tashiro, Masahiro Terada
Summary: Cu-catalyzed reactions of N-alkoxy-2-methylanilines and alcohols in the presence of IPrCuBr and AgSbF6 afford meta-aminophenol derivatives through a [1,3]-rearrangement and an oxa-Michael reaction.
Article
Chemistry, Physical
Jingyang Sun, Yoona Song, Jae-Sang Ryu
Summary: The gold-catalyzed cascade process for the synthesis of dihydroquinazolinone scaffolds exhibits good yields, high regioselectivity, and broad substrate scope. It can also be applied to the synthesis of tetracyclic dihydroquinazolinones and seven-membered ring-fused dihydroquinazolinones.
Article
Chemistry, Multidisciplinary
Yan-Bo Li, Hu Tian, Shuai Zhang, Jun-Zhao Xiao, Liang Yin
Summary: In this study, a copper(I)-catalyzed reaction of diarylphosphines and O-benzoyl hydroxylamines was developed, leading to the synthesis of aminophosphinites and P-chiral aminophosphinites. The reaction mechanism was proposed and further transformation to P-chiral phosphines was achieved.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Tim Glaesel, Haijun Jiao, Marko Hapke
Summary: In this study, the Co-II-catalyzed [2+2+2] cycloaddition of functionalized diynes and phosphaalkynes was reported, resulting in an array of structurally interesting phosphinines. The combination of dppbenz and CoI2 was found to be the most suitable and active catalyst system under microwave reaction conditions. Chemoselective cyclizations of phosphaalkynes in the presence of nitriles were observed, and various carbonyl functionalities were tolerated as well.
Review
Chemistry, Multidisciplinary
Xueling Mo, Rui Guo, Guozhu Zhang
Summary: Alkynes are important functional groups in organic chemistry and there have been significant efforts in synthesizing chiral alkynes. The asymmetric C(sp(3))-C(sp) cross-coupling offers a complementary strategy through radical-initiated process. However, controlling the stereochemistry of highly reactive and unstable radical intermediates has been a long-standing challenge. In order to address this problem, various chiral ligands have been developed to initiate the reaction and achieve enantiocontrol of alkyl radicals. This review summarizes recent developments in copper-catalyzed enantioselective alkynylation of prochiral alkyl radicals and provides insights into the mechanism.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Yetong Zhang, Lepeng Chen, Yinlin Shao, Fangjun Zhang, Zhongyan Chen, Ningning Lv, Jiuxi Chen, Renhao Li
Summary: The study presents a three-component tandem reaction allowing the synthesis of polysubstitution quinolines using 2-aminobenzonitriles, arylboronic acids, and ketones. This method is practical, efficient, and delivers functional quinolines with moderate to good yields and high functional group tolerance. Additionally, a new method for introducing halogen substituents into the target products has been developed, showing potential for further synthetic elaborations.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Biochemistry & Molecular Biology
Anna N. Philippova, Daria V. Vorobyeva, Pavel S. Gribanov, Ivan A. Godovikov, Sergey N. Osipov
Summary: An efficient method for the selective preparation of trifluoromethyl-substituted azepin-2-carboxylates and their phosphorous analogues has been developed via Cu(I)-catalyzed tandem amination/cyclization reaction of functionalized allenynes with primary and secondary amines.
Article
Chemistry, Organic
Alma R. Perez, Evan C. Bornowski, Lei Chen, John P. Wolfe
Summary: The synthesis of indanes containing substituted cyanomethyl groups at C2 has been achieved through Pd-catalyzed coupling reactions. Alkenyl triflates were used to generate partially saturated analogues via similar transformations. The use of a preformed BrettPhosPd(allyl)(Cl) complex as a precatalyst was crucial for the success of these reactions.
Article
Chemistry, Organic
Haiyun Peng, Yangyi Zhang, Guisheng Deng
Summary: The silver(I)-catalyzed tandem reaction of enynones with 4-alkenylisoxazoles provides a convenient method for the synthesis of 2-(furan-2-yl)-1,2-dihydropyridines. The reaction proceeds through the formation of (2-furyl)metal carbene intermediate, N-O bond cleavage of 4-alkenyl isoxazoles/rearrangement, subsequent 6 pi electrocyclic reaction, and [1,5] H-shift. This atom-economic strategy allows for the efficient construction of both the 1,2-dihydropyridine skeleton and furan framework in a one-pot reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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)