Article
Chemistry, Multidisciplinary
Yue Jin, Yashi Zou, Yanhua Hu, Yunxi Han, Zhenfeng Zhang, Wanbin Zhang
Summary: A highly efficient azole-directed cobalt-catalyzed asymmetric hydrogenation of alkenes has been developed. This method allows for the synthesis of chiral pyrazole compounds with quantitative yields and excellent enantioselectivities (up to 99% ee) under mild conditions. The reaction can be conducted on a gram scale with high turnover numbers (up to 2000 TON) and has demonstrated several useful applications including the introduction of beta-chirality to drug intermediates containing an azole ring.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Physical
Zhong-zuo Yan, Zhen-bing Lv, Dong-ze Zhao, Meng-bi Guo, Yi-tong Wang, Zhuang Hou, Chun Guo
Summary: A series of novel boron-containing azoles were designed, synthesized, and characterized via various spectroscopic techniques. The target compounds showed excellent antifungal activity against fluconazole-sensitive Candida strains and even demonstrated superior efficacy against fluconazole-resistant strains. Furthermore, compound N01 exhibited negligible toxicity to mammalian cells and had potential as a CYP51 inhibitor.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Multidisciplinary
Stephan P. Blum, Lukas Schaffer, Dieter Schollmeyer, Siegfried R. Waldvogel
Summary: This electrochemical synthesis protocol demonstrates a direct method for symmetrical sulfamides from anilines and SO2 mediated by iodide, which is an emerging functional group in drug design. The highlights include the direct use of SO2 from a stock solution and no necessity of any supporting electrolyte, with yields up to 93% demonstrated in 15 examples.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Inorganic & Nuclear
Xizhou Zheng, Iker del Rosal, Xian Xu, Yingming Yao, Laurent Maron, Xin Xu
Summary: Calcium-mediated reaction successfully catalyzes regioselective benzylic C-H bond addition of alkylpyridines, resulting in alkylated pyridine derivatives.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xuewei Luo, Bo Zhang, Chanjuan Xi
Summary: The photoredox-catalyzed hydroxydifluoroacetylation of alkenes with FSO2CF2CO2Me and H2O was achieved under mild conditions, using fac-[Ir(ppy)(3)] as the photocatalyst, yielding CF2CO2Me-containing alcohols and/or difluorolactones in high yields with high regioselectivity.
Article
Chemistry, Medicinal
Changjun Yu, Ruiyao E., Xiao-Wei Zhang, Wen-Qian Hu, Guangjun Bao, Yiping Li, Yuyang Liu, Zeyuan He, Jingyue Li, Wen Ma, Ling-Yun Mou, Rui Wang, Wangsheng Sun
Summary: Innovations in synthetic chemistry play a crucial role in drug discovery and development. Developing simple and effective methods for synthesizing medicinal modules is of great significance. In this study, we successfully developed a NaClO-mediated cross installation of indoles and azoles, which are commonly found in drugs and natural products. This method provides a convenient route for accessing a library of N-linked 2-(azol-1-yl) indole derivatives and allows late-stage modification of drugs, natural products, and peptides. Furthermore, the biological screening of the library demonstrated promising anticancer activities against A549 and NCI-H1975 cells, providing a potential lead for anticancer drug discovery.
Article
Chemistry, Organic
Jingjing He, Chuan Liu, Yupian Deng, Qianding Zeng, Yi Zhang, Ying Liu, Pai Zheng, Song Cao
Summary: A mild and efficient DBN-mediated addition reaction was developed for the synthesis of various β-trifluoromethyl nitrogen-containing heterocycles and β-trifluoromethyl amines using α-(trifluoromethyl)styrenes and diazoles, triazoles, tetrazoles, and primary, secondary, and secondary cyclic amines.
Article
Chemistry, Organic
Xiaoman Li, Jiawei Huang, Liang Xu, Ping Liu, Yu Wei
Summary: In this study, a tetrabutylammonium tribromide-mediated three-component reaction of alkenes, diselenides, and sulfoximines was established, providing a direct and metal-free access to diverse beta-arylseleno sulfoximine derivatives. This regioselective sulfoximido-selenization protocol proceeds efficiently under mild and ambient conditions with generally good yields. The strategy is characterized by step and atom economy, practicability, a broad substrate scope, and gram-scale synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Guo-Qing Cui, Jing-Cheng Dai, Yan Li, Yuan-Bo Li, Duo-Duo Hu, Kang-Jie Bian, Jie Sheng, Xi-Sheng Wang
Summary: The first example of copper-catalyzed ring-opening, enantioselective arylation of cyclic ketoxime esters has been developed with high yield and excellent enantioselectivity. The side-arm bis(oxazoline) ligand plays a significant role in this asymmetric catalytic transformation, providing an efficient route to construct diverse chiral omega,omega-diaryl alkyl nitriles. This synthetic method also demonstrates its utility in further derivatizing the omega,omega-diaryl alkyl nitrile to the corresponding amide.
Article
Chemistry, Multidisciplinary
Marion H. Emmert, Cyndi Qixin He, Akshay A. Shah, Stephanie Felten
Summary: This manuscript presents a metal-free approach to azole C-H functionalization via Lewis acid mediated azole C-H deprotonation, demonstrating the potential of new C-C bond formations. The study uses DFT calculations to identify key interactions in the mechanism of the reaction and enables the C-H aminoalkylation of initially unreactive substrates through an in situ protecting/activating group strategy. Overall, the work showcases the versatility of a readily available, Si-based Lewis acid in facilitating diverse C-C bond formations in azoles.
Article
Chemistry, Applied
Xin Chen, Yun-Tao Shen, Zhi-Wei Zhao, Yu-Jian Hou, Bo-Xun Sun, Tai-Gang Fan, Ya-Min Li
Summary: This study proposes a method for the oxy-/amino-difluoromethylthiolation of beta,gamma-unsaturated oximes/hydrazones using PhSO2SCF2H as the difluoromethylthiolation reagent under mild conditions, demonstrating good functional group tolerance and scalability.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Sebastian Engl, Oliver Reiser
Summary: This study presents a catalyst- and metal-free visible-light-mediated protocol for iodoamination of various olefins, offering high yields under environmentally friendly conditions. The protocol allows for late-stage functionalization of bioactive molecules and can be scaled to gram quantities of product, providing numerous possibilities for further transformations.
Article
Chemistry, Multidisciplinary
Xiaoyuan Wan, Dahan Wang, Huawen Huang, Guo-Jiang Mao, Guo-Jun Deng
Summary: In this study, a novel visible light-induced photocatalytic system for intramolecular hydroarylation of unactivated alkenes is reported. Thiosulfonate compounds were identified as the crucial radical precursor mediating the Minisci-type intramolecular cyclization reaction. The reaction conditions were optimized, leading to the formation of a wide range of pyridyquinazolinone and pyrroloquinazolinone products in moderate to good yields.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Pu Chen, Zan Chen, Bi-Quan Xiong, Yun Liang, Ke-Wen Tang, Jun Xie, Yu Liu
Summary: A novel synthesis method is reported, involving visible-light-mediated reactions that enable the introduction of two different functional groups on carbon-carbon triple bonds in a tandem manner, leading to the successful preparation of the desired product.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Zhe Meng, Xiaoyu Zhang, Min Shi
Summary: A novel fluoroalkylation and cycloisomerization cascade reaction of ene-VDCP with ethyl iododifluoroacetate or perfluoroalkyl iodide under visible-light irradiation is reported in this study, providing the desired fluorinated cyclization products in moderate to good yields and showing good functional group tolerance. Mechanistic investigations suggest the presence of a radical chain process in this reaction.
ORGANIC CHEMISTRY FRONTIERS
(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)