Article
Chemistry, Multidisciplinary
Nieves P. P. Ramirez, Jerome Waser
Summary: An asymmetric 3-component reaction catalyzed by a Cu-I-BOX catalyst was developed for the synthesis of chiral trifluoromethylated propargyl ethers and anilines. The reaction showed high enantioselectivity and yield with various nucleophiles and different electrophiles. The method also exhibited good diastereoselectivity with chiral substrates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yan Long, Yun Wang, Yue-You Chen, Wen-Yong Han, Nan-Wei Wan, Wei-Cheng Yuan, Yong-Zheng Chen, Bao-Dong Cui
Summary: This article describes an inexpensive copper-catalyzed sequential reaction process for synthesizing structurally diverse spiro-dihydropmolo[1,2-a]quinoxaline derivatives. The significance of this method is highlighted by its ability to convert synthetic compounds into potentially bioactive molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Prafull A. Jagtap, Manjunath S. Lokolkar, Bhalchandra M. Bhanage
Summary: A simple, cost-effective, and straightforward method for the synthesis of 2,3-disubstituted indole scaffolds was developed. The reaction involves copper-mediated tandem hydroamination followed by C-H annulation of unprotected anilines with internal alkynes. The reaction proceeds well with Cu(OAc)(2)& BULL;H2O and trifluoroacetic acid (TFA), providing various substituted indole derivatives in moderate to good yields. The process is compatible with primary and secondary anilines as well as aromatic/aliphatic alkynes. High-purity copper nanoparticles can be recovered after the reaction, demonstrating the cost-effectiveness and environmentally benign nature of the protocol.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hue Thi Buu Bui, Kiep Minh Do, Huy Tran Duc Nguyen, Hieu Van Mai, Thanh La Duc Danh, De Quang Tran, Hiroyuki Morita
Summary: In this study, twenty novel quinazolin-4(3H)-one derivatives were synthesized and several compounds were found to possess cytotoxic activities against MCF-7 and A549 cells based on cell viability assays.
Article
Chemistry, Organic
Theo V. C. Russo, Marcus M. Sa
Summary: The synthesis of novel allylic alpha-diazo carbonyl compounds was achieved through a one-pot strategy involving base-catalyzed allylation of 1,3-dicarbonyls with readily available allylic bromides followed by the deacylative diazo transfer reaction. The use of simple and inexpensive reagents, non-toxic solvents, and mild reaction conditions further highlight the broad substrate scope and synthetic utility of these compounds. Rhodium-catalyzed transformations of alpha-diazo-gamma,delta-unsaturated esters led to different product formations depending on the substrate and catalyst employed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Zhen Yao, Zhenli Luo, Yixiao Pan, Xin Zhang, Bohan Li, Lijin Xu, Peng Wang, Qian Shi
Summary: A metal-free tandem one-pot synthesis of 3,3-disubstituted 3,4-dihydroquinoxalin-2(1H)-ones has been achieved using visible-light photoredox catalysis. The method provides the desired products in high yields for various substrates, demonstrating great potential for practical applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Simra Faraz, Abu Taleb Khan
Summary: A green synthesis of 2,3-diarylquinolines is presented using a one-pot three-component reaction with arylamines, benzaldehyde, and styrene oxide. The reaction is catalyzed by 20 mol% p-TSA center dot H2O at 120 degrees C and does not require metal catalysts, additives, or extra oxidants. This method is advantageous due to its simplicity, wide substrate scope, short reaction time, high atom economy, regioselectivity, and good yields. In a single step, it forms one C-N bond and two C-C bonds.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Babar Hussain Shah, Sardaraz Khan, Can Zhao, Yong Jian Zhang
Summary: An efficient method for the synthesis of 2,3-dihydrofurans with a quaternary stereocenter has been developed through Pd-catalyzed asymmetric allylic cycloaddition and a retro-Dieckmann fragmentation cascade. The one-pot process involves the allylic cycloaddition of vinylethylene carbonates with 3-cyanochromone and subsequent base-assisted retro-Dieckmann fragmentation, leading to chiral 3,4-disubstituted 2,3-dihydrofurans with high yields and excellent enantioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Khawla Boudebbous, Raouf Boulcina, Dominique Harakat, Thierry Roisnel, Abdelmadjid Debache
Summary: A series of compounds bearing ethyl carbamate moiety were synthesized via a facile synthetic route. The structures of the synthesized compounds were elucidated using spectroscopic techniques and X-ray diffraction. This synthesis method offers readily available starting materials, milder reaction conditions, and environmental friendliness.
Article
Chemistry, Organic
Tao Fan, Xianli Ma, Yan Liu, Caina Jiang, Yanli Xu, Yanyan Chen
Summary: A visible-light-induced tandem reaction between allenes and selenesulfonates was developed, yielding (E)-2,3-disulfonyl-propene derivatives in moderate to good yields. This reaction is characterized by its simple operation, good regioselectivity and stereo-selectivity, and wide tolerance towards functional groups.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Neetu Yadav, Kovuru Gopalaiah, Jyoti Pandey, Rajamani Nagarajan
Summary: In this study, the usage of inherent redox couplets in PrVO4 with a zircon-type structure for tandem oxidative transformation was investigated. Monophasic PrVO4 exhibited a tetragonal zircon-type structure and the existence of redox couplets Pr3+/Pr4+ and V4+/V5+ was confirmed. The catalytic utility of zircon PrVO4 for the one-pot synthesis of 2,3-disubstituted quinolines through the oxidative tandem reaction of 2-aminobenzylalcohols with 1,3-dicarbonyl compounds was demonstrated, achieving good to excellent yields.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Organic
Yu-Hong Ma, Xiao-Yu He, Long Wang, Qing-Qing Yang
Summary: A PPh3-triggered tandem strategy has been developed for the efficient synthesis of valuable 2,3-disubstituted benzofuran derivatives from aryl or alkyl acyl chlorides and o-quinone methides. This method features mild reaction conditions, simple operation, and a broad substrate scope.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jilai Wu, Song Xie, Likai Zhou, Yixuan Liu, Yaxin Cui, Xiaoyan Huang, Chao Wei, Xiaoliu Li, Chunfang Zhang, Hua Chen
Summary: A novel furantetrahydro-quinoline derivative was efficiently prepared using d/l-ribose with a 2,3-O-isopropylidenegroup through the aza-Diels-Alder mechanism. This method demonstrates high atom and step economy, high stereo-selectivity, and gram-scale synthesis (yield 67%).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Anqiao Zhu, Yu Sun, Jingru Lai, Ziyan Chen, Xiaoli Bu, Yan-Ni Yue, Mengtao Ma, Fei Xue
Summary: A efficient and reliable method for the synthesis of diverse 2,3-substituted indanones through a rhodium-catalyzed tandem reaction has been developed. The method is compatible with various functional internal acetylenes, especially natural and functionalized alkynes derivatives, giving good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Bei Zhang, Jinhang Yu, Xin Wu, Zeyu Chai, Guoying Zhao, Zihan Li, Honglan Kang, Xin Lv, Liejin Zhou
Summary: A variety of furo[2,3-e][1,4]diazepin-3-one derivatives were successfully synthesized through a simple method, showing potential biological and medicinal value.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ming Bao, Jinzhou Chen, Chao Pei, Sujie Zhang, Jinping Lei, Wenhao Hu, Xinfang Xu
Summary: An unprecedented gold-catalyzed ketene C=O/C=C bifunctionalization method has been developed, initiated by gold-catalyzed Wolff rearrangement of diazoketone to form the ketene intermediate, followed by nucleophilic addition and terminated with two divergent cyclization processes. Depending on the nucleophiles used, different cyclization pathways are observed, leading to the formation of different products, providing a novel reaction pattern for the ketene dual functionalization.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Applied
Ming Bao, Xiongda Xie, Wenhao Hu, Xinfang Xu
Summary: A gold-catalyzed carbocyclization/C=N bond formation cascade reaction has been developed for the synthesis of polyfunctionalized 4-iminonaphthalenones and indenes in good to high yields under mild reaction conditions. The resulting products could be converted into multi-substituted 2-naphthol derivatives in high yields.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Kemiao Hong, Shanliang Dong, Xinxin Xu, Zhijing Zhang, Taoda Shi, Haoxuan Yuan, Xinfang Xu, Wenhao Hu
Summary: An enantioselective intermolecular Mannich-type interception of phenolic oxonium ylides with imines has been developed using cooperative catalysis with achiral dirhodium complex and chiral phosphoric acid. The synthesis of enantioenriched 2,2-disubstituted dihydrobenzofurans with good to high yield and high to excellent enantioselectivity under mild conditions was achieved. Preliminary antitumor activity study showed high anticancer potency of the reduction product 7 against human lung adenocarcinoma cells (A549 cells, IC50 = 9.13 mu M).
Article
Chemistry, Organic
Xiangrong Liu, Xue Tian, Jiawu Huang, Yu Qian, Xinfang Xu, Zhenghui Kang, Wenhao Hu
Summary: An enantioselective three-component reaction of alpha-propargylic-3-indolymethanol with diazoindolinone and alcohol has been achieved under the cocatalysis of Rh(II) and chiral phosphoric acid (CPA). The reaction proceeds through regio- and enantiospecific addition of an in situ formed oxonium ylide to the alpha-propargylic indole iminium ion, providing an efficient access to chiral propargylic indole derivatives with high yields and enantioselectivities.
Article
Chemistry, Physical
Yong-Liang Su, Geng-Xin Liu, Luca De Angelis, Ru He, Ammar Al-Sayyed, Kirk S. Schanze, Wen-Hao Hu, Huang Qiu, Michael P. Doyle
Summary: This study demonstrates the efficient generation of functionalized derivatives through photocatalyzed multicomponent reactions using nitrogen aromatic heterocycles, alkenes, and diazo compounds. The reaction shows high functional group tolerance and exacting regioselectivities. Mechanistic studies, including photophysical measurements, provide insights into this radical cascade reaction.
Article
Chemistry, Applied
Kang Guo, Chen Gu, Yun Li, Xiaofei Xie, Honglin Zhang, Kang Chen, Yingguang Zhu
Summary: In this study, a photoredox catalyzed trifluoromethyl radical-triggered trifunctionalization of 5-hexenenitriles via cyano group migration is reported. The migration of the cyano group shows high chemo-selectivity even in the presence of aryl or heteroaryl groups as competitors. This protocol provides a simple access to CF3-containing compounds with high molecular complexity and functional group diversity. The successful gram-scale reaction and the versatility of the products in derivative synthesis illustrate the potential value of this transformation in synthetic chemistry.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Xiang Fu, Jie Tang, Ruyu Hua, Xiaoqian Li, Zhenghui Kang, Huang Qiu, Wenhao Hu
Summary: This study reports two DNA-compatible reactions with alkenes and diazo compounds, providing hydroalkylation and cyclopropanation products in moderate to excellent yields. These transformations not only offer new access to C(sp3)-C(sp3) bond formation in DELs with excellent functional group tolerance, but also represent practical ligation methods to introduce functionalized molecules into DNA.
Article
Chemistry, Applied
Shujun Cao, Huaigui Li, Xinjie Teng, Huaxing Si, Rongshun Chen, Yingguang Zhu
Summary: A domino cyclization of oxime esters and imines has been achieved by dual photoredox/copper catalysis, producing a variety of structurally diverse fully substituted dihydropyrimidines with high molecular complexity and functional group diversity.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Weidong Yuan, Anling Qu, Yan Li, Huaigui Li, Kang Chen, Yingguang Zhu
Summary: In this work, a photoredox/Ti dual-catalyzed dehydroxylation of cyclobutanone oximes has been established. The reaction proceeds under mild conditions, resulting in the formation of cyanoalkyl-substituted oxoindolines through a cascade radical addition/cyclization with N-acrylamides. The reaction shows broad substrate scope, good functional group tolerance, and can be used for late-stage functionalization of complex molecules and gram-scale synthesis, highlighting its potential value in organic synthesis.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Yan Li, He Tong, Yukun Li, Kang Chen, Yingguang Zhu
Summary: We have developed a visible light-induced transition metal-free benzylic C(sp(3))-C(sp(2)) defluorinative coupling reaction between indole derivatives and polyfluoroarenes via the sequential electron transfer-proton transfer (ET/PT) process, resulting in various polyfluorinated diarylmethanes. This protocol offers mild reaction conditions and good functional group tolerance.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Jianlin Chun, Yukun Li, Xiaofei Xie, Kang Guo, Daoyuan Zhao, Kang Chen, Yingguang Zhu
Summary: This study develops a photoinduced copper-catalyzed method for the enantioconvergent remote alkynylation of N-hydroxyphthalimide esters via 1,4-heteroaryl migration. A broad range of heteroaryl-tethered chiral alkynes is synthesized with good regio- and enantioselectivities. The chiral-ligand-coordinated copper species serves as both the photoredox and cross-coupling catalyst, providing a new platform for enantioconvergent remote alkynylations.
Article
Chemistry, Multidisciplinary
Kang Guo, Chunyu Han, Xiaofei Xie, Bin Chen, Shujun Cao, Weidong Yuan, Kang Chen, Fang Liu, Yingguang Zhu
Summary: A photoredox/Cu dual catalyzed enantioselective remote cyanation via 1,4-heteroaryl migration has been developed. Experimental and computational studies were conducted to explore the reaction mechanism and explain the origin of regio- and enantioselectivities. This methodology demonstrates mild conditions, a wide substrate scope and good selectivities, providing a unique approach to catalyst-controlled asymmetric backbone recombination via functional group migration.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Shujun Cao, Chongchong Ma, Xinjie Teng, Rongshun Chen, Yun Li, Weidong Yuan, Yingguang Zhu
Summary: A novel and efficient synthesis method for fully substituted 1H-imidazoles has been developed through photoredox/copper cocatalyzed domino cyclization of oxime esters, aldehydes, and amines. This method exhibits good functional group tolerance, broad substrate scope, high step economy, high bond-forming efficiency, and the ability for gram-scale synthesis.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Shujun Cao, Weidong Yuan, Yun Li, Xinjie Teng, Huaxing Si, Rongshun Chen, Yingguang Zhu
Summary: A photoredox/copper cocatalyzed domino cyclization of oxime esters with TMSCN has been developed to obtain structurally novel tetrasubstituted pyrazines. This method demonstrates high bond-forming efficiency, step economy, broad substrate scope, and gram-scale synthesis. Preliminary bioactivity evaluation of the pyrazine products shows promising antifungal activities.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Su Zhou, Qianqian Liu, Ming Bao, Jie Huang, Junjian Wang, Wenhao Hu, Xinfang Xu
Summary: A new synthesis method for 2-indolyl indolone N-oxides via gold(i)-catalyzed cascade reaction of o-nitroalkynes with indoles has been developed, leading to highly efficient conversion into 2-indolylbenzoxazinone with strong blue fluorescence. The synthesized compounds were also evaluated for their antitumor activity in small cell lung cancer, with compounds 3d and 4s showing high anticancer potency against SCLC cells.
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)
