Article
Chemistry, Organic
Lu Cheng, Mengdan Wang, Yajie Yang, Zongkang Wang, Yilin Zhu, Lingkai Kong, Yanzhong Li
Summary: An atom-economical transition-metal-free protocol for the stereoselective synthesis of conjugated trienes has been developed via base promoted C-C sigma-bond cleavage reactions of allyl carbonyl compounds. This methodology efficiently constructs a broad range of conjugated trienes with the advantages of mild reaction conditions, low cost, and operational simplicity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Dongping Cheng, Yinqiang Shen, Ziliang Wu, Xiaoliang Xu, Jizhong Yan
Summary: A novel oxidative coupling of hydrazones and 1,3-diarylpropenes mediated by DDQ was disclosed, leading to the selective generation of 1,2-dihydropyridazines or pyrazoles through subsequent cyclization under metal-free conditions. The mechanisms of the coupling and cyclization were proposed in the study.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Wanjun Chen, Yaping Cheng, Tao Zhang, Yu Mu, Wenqi Jia, Guodu Liu
Summary: A nickel-catalyzed stereoselective asymmetric intramolecular reductive coupling of N-1,6-alkynones was reported, achieving efficient synthesis of versatile functionalized chiral pyrrolidines with high yields, excellent stereoselectivity, and enantioselectivity. The developed reaction is applicable to a broad substrate scope and can be scaled up to gram scale without loss of enantioselectivity. The study also investigated ligand effects and reaction mechanism, suggesting wider applications in organic synthesis and chemical biology, and potential for further explorations in new research fields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xiao-Wen Zhang, Ming-Hui Zhu, Hai-Xiang Zeng, Qi-Yang Li, Wen-Bo Liu
Summary: This study presents a highly enantioselective NiH-catalyzed hydrocyclization of alkynones, yielding an array of enantioenriched heterocyclic tertiary allylic alcohols. The choice of precatalysts significantly influences the selectivity of the products, with yields reaching up to 81%.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Takashi Mino, Toshiki Yamaoka, Kohei Watanabe, Chihiro Masuda, Shohei Kasano, Yasushi Yoshida, Ryo Takita, Yoshio Kasashima, Masami Sakamoto
Summary: P,olefin ligand/palladium catalyst systems can easily afford the corresponding 2-substituted 3-allylindole derivatives in good to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yi-En Liang, Chih-Yu Kan, Balaji D. Barve, Yen-An Chen, Wen-Tai Li
Summary: A novel Pd-catalyzed reaction was developed for the synthesis of 4H-furo[3,2-c]chromenes and xanthones through tandem cyclization/cross-coupling reaction of 3-alkynyl chromone with aryl iodide. The reaction selectively controlled by KF or a bidentate phosphine ligand exhibited a rare difunctionalization of alkynes through O-attack/5-exo-dig and C-attack/6-endo-dig cyclization. A one-pot tandem process was demonstrated directly from gamma-alkynyl-1,3-diketone for this method.
Article
Chemistry, Organic
Shuangshuang Li, Ju Qiu, Bowen Li, Zuolian Sun, Peizhong Xie, Teck-Peng Loh
Summary: A practical palladium/calcium catalytic system was developed for dehydrative allylation with unactivated allylic alcohols, utilizing ethanol solvent with a water additive to accelerate proton transfer. This system allowed for smooth reactions at room temperature, producing allylic compounds with a variety of functional groups in high to excellent yields.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Jia-Hao Xie, Chao Zheng, Shu-Li You
Summary: A novel Pd-catalyzed method for dearomative methoxyallylation of 3-nitroindoles with allyl carbonates has been developed, achieving high yields and diastereoselectivity. The method demonstrates good scalability and practicality with relatively low catalyst loading. Kinetic experiments suggest that the nucleophilic attack of the alkoxide anion is the rate-determining step in this reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Ya-Zhen Du, Yu-Jiao Wang, Qing-Yang Zhao, Li-Ming Zhao
Summary: This study describes two types of C5 functionalization reactions of chromones with allyl alcohols, resulting in diverse 5-substituted chromones by modulating the catalysts. Further functionalizations of these 5-substituted chromones were achieved, demonstrating the superiority of this method. Notable features of these new methods include readily available precursors, tunable reactivity, exclusive C5-selectivity, and easy derivatization of products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kaili Cen, Jiahao Wei, Yuan Liu, Zhixuan Tan, Xinye Wang, Dahan Wang, Wei-Min He, Jinhui Cai
Summary: This study describes the electrochemical synthesis of various 3-selenylated chromones under transition-metal-free and chemical-oxidant-free conditions. The method features mild conditions, easy operation, and wide substrate scope.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Danhua Ge, Xin-Long Luo, Xi Tang, Chao-Bin Pang, Xin Wang, Xue-Qiang Chu
Summary: A novel method has been developed for the synthesis of biologically and pharmaceutically active 2,3-diarylpyridine derivatives using a three-component [3 + 2 + 1] annulation strategy with allylic alcohols, ketones, and ammonium acetate as substrates. The method operates efficiently under metal-free conditions and allows for site-specific selectivity in obtaining the desired heterocycles with good functional group tolerance.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Yingying Zhang, Yating Huang, Kewei Yu, Xiaoxiang Zhang, Wenhua Yu, Jiale Tang, Yiran Tian, Wanxing Wei, Zhuan Zhang, Taoyuan Liang
Summary: Herein, we report a novel iron and iodine cooperative catalytic system for the synthesis of diverse 2-amino-3-alkylindoles. The method exhibits good substrate and functional group compatibility, and the catalyst system and feedstocks are readily available, showing great potential for further exploration of biological activities.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Ji-Hong Xia, Qian Chen, Jin-Wei Yuan, Wei-Shuo Shi, Liang-Ru Yang, Yong-Mei Xiao
Summary: A practical and metal-free approach for the regioselective selenation of chromones has been developed using Selectfluor reagent under mild conditions. This method demonstrates a wide substrate scope and provides 3-selenylated chromones in good to excellent yield with high selectivity. An ionic mechanism is proposed for this transformation. The application of potassium thiocyanate with enaminones in this reaction also yields thiocyano chromones.
Article
Chemistry, Multidisciplinary
Masahiro Sai
Summary: This study introduces a novel base-promoted reaction method for the diastereoselective synthesis of 1,3-diols with three contiguous stereogenic centers from allylic alcohols and aldehydes via allylic isomerization-initiated Aldol-Tishchenko reactions. Unlike traditional systems, this method utilizes readily available allylic alcohols as nucleophiles instead of enolizable aldehydes and ketones, offering a more sustainable and efficient approach to complex diol synthesis.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Organic
Yibo Chen, Zhenbo Gao
Summary: A novel method has been developed for the mild and efficient synthesis of allyl sulfides using allyl alcohols and thiols as substrates, with Sn(OTf)(2) as a catalyst. The method allows for the synthesis of a diverse range of allyl sulfides, including linear and cyclic derivatives, with good yields. This approach shows high efficiency, with gram-scale reactions achieving over 90% yields using just 1 mol% catalyst.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Di Hu, Chao Pi, Wei Hu, Xiliang Han, Yangjie Wu, Xiuling Cui
Summary: In this study, a Ru(III)-catalyzed annulation reaction of 2-aminoaromatic aldehydes (ketones) and isoxazoles to produce diverse 3-cyanoquinolines has been developed. The isoxazole served as a cyclization reagent and a non-toxic cyano source via N-O bond cleavage, leading to the formation of variously substituted (especially 6- or 7-substituted) quinolines. This efficient and versatile method offers wide functional group compatibility and avoids the use of toxic cyano sources. Furthermore, the synthesized 3-cyanoquinoline can undergo further chemical transformations to yield valuable skeletons, demonstrating its potential in synthetic applications.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Haopeng Xu, Chao Pi, Yangjie Wu, Xiuling Cui
Summary: An efficient multi-component reaction has been developed for the synthesis of 2,3-disubstituted tetrahydrofurans in a one-pot manner, providing a wide array of alpha-indole-beta-sulfonyl tetrahydrofurans in good yields with excellent selectivity, while avoiding the use of various additives and transition metals as catalysts.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Xia Mi, Beibei Cui, Jingyu Zhang, Chao Pi, Xiuling Cui
Summary: A visible light-induced C-H trifluoromethylation of quinoxalin-2(1H)-ones using CF3SO2Cl as the CF3 radical source under photocatalyst-free conditions is reported in this study. The reaction proceeds smoothly through a radical process in the absence of photocatalyst and oxidant, offering an efficient and green method for the synthesis of 3-trifluoromethyl quinoxalin-2(1H)-ones.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Zhichao Chen, Hong Zhang, Shu-Feng Zhou, Xiuling Cui
Summary: A photoredox-catalyzed method for generating sulfonated oxazolines has been developed, involving sequential insertion of sulfur dioxide, intermolecular sulfonylation of alkenes, and intramolecular cyclization via a radical process. This protocol is characterized by good compatibility of functional groups and mild reaction conditions, and the sulfonated oxazolines can be efficiently transformed into beta-amino alcohols, which are important moieties in pharmaceuticals.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Applied
Jie Ren, Liu Yang, Chao Pi, Xiuling Cui, Yangjie Wu
Summary: In this study, a rhodium(III)-catalyzed divergent C-H bond functionalization of N-aryl amidines with iodonium ylides was described. Carbazolones and zwitterionic salts were synthesized through intermolecular annulation and intramolecular proton transfer under different reaction conditions. This protocol is simple to perform and can tolerate a variety of functional groups, making it practically useful for post-modification of pharmaceutical molecules.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Wenxiang Wang, Chao Pi, Xiuling Cui, Yangjie Wu
Summary: A TBAI-catalysed [4+4]-cyclization reaction was developed for the synthesis of oxa-bridged eight-membered heterocycles from anthranils and hydrazones. Mechanistic studies showed the in situ generation of vinyldiazenes from hydrazones, followed by an aza-Michael addition and subsequent annulation. This strategy overcomes the limitations of anthranils in organic chemistry and provides a high efficiency and atom economical approach.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Jian Shen, Bo Cui, Junwei Huang, Shenghui Lin, Xiuling Cui
Summary: A highly efficient strategy to construct benzo[d][1,3]diazepines via selective C-H bond activation of N-aryl amidines and coupling with alkynyl cyclobutyl acetates was successfully achieved by Ru-II-catalyzed [5+2] cyclization. This protocol features excellent regioselectivity, wide substrate tolerance, and mild reaction conditions, which might be potentially applied in the discovery of lead compounds for the development of new drugs.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xuelin Yue, Yijie Gao, Junwei Huang, Yadong Feng, Xiuling Cui
Summary: An efficient method for the synthesis of N substituted indenoisoquinolinones has been developed via rhodium(III)-catalyzed C- H bond activation and subsequent [4 + 2] cyclization. The reaction uses 2-phenyloxazolines and 2-diazo-1,3-indandiones as starting materials and proceeds through C-H functionalization, intramolecular annulation, elimination, and ring opening in one pot under mild conditions, yielding a series of indeno[1,2-c]isoquinolinones with up to 93% yield. This method demonstrates excellent atom-and step-economy and provides a novel strategy for the synthesis of N substituted indenoisoquinolinones and their study of biological activities.
Article
Chemistry, Organic
Jie Ren, Chao Pi, Xiuling Cui, Yangjie Wu
Summary: Transition metal-controlled divergent annulation reactions of azomethine imines with iodonium ylides via C centered [1,2]-rearrangement have been developed. The azomethine imino group, as a switchable and transient directing group (DG), underwent intramolecular nucleophilic addition and in situ generated bicyclic diaziridine, which facilitated the C-centered [1,2]-rearrangement and subsequent divergent annulations in the presence of different metal complexes as the catalysts. The benzo[c]chromen-1-one and pyrano[de]isochromene scaffolds could be independently constructed with Rh(III) and Ru(II), respectively. It was worth noting that the azomethine imino group was employed first as the switchable DG through rearrangement progress.
Article
Chemistry, Organic
Xinxin Yan, Chao Pi, Xiaofan Cui, Xiuling Cui, Yangjie Wu
Summary: A novel approach to construct multiple heterocycles with high selectivity has been developed through Rh(III)-catalyzed two-or three-component cyclization reaction using simple and readily available starting materials: N-methoxybenzamides, 2-butyne biscarbonate, and maleimides. This methodology provides an efficient strategy for the synthesis of diverse and complicated heterocycles in a one-pot manner, and it exhibits excellent features of extremely mild reaction conditions, easy operation, excellent regioselectivity, and good functional group compatibility.
Review
Chemistry, Applied
Xiaofan Cui, Remi Chauvin, Chao Pi, Yangjie Wu, Xiuling Cui
Summary: This review presents recent progress in the use of vinylene carbonate as a reactant in transition metal-catalyzed C-H bond activation/cyclization reactions. By analyzing and comparing different reaction models, it highlights the advantages of using vinylene carbonate as a surrogate for ethynol and other reactants, and discusses related mechanisms and synthetic applications.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Xiang Zhao, Junwei Huang, Yadong Feng, Xiuling Cui
Summary: The efficient rhodium(III)-catalysed C-H activation of 3-aryl-1-H-indazoles with readily accessible vinylethylene carbonate has been reported. Allyl alcohol substituted 3-aryl-1-H-indazoles were obtained with broad functional groups tolerance and favorable stereoselectivity. Significant to note is the selective activation of C-H and C-O bonds in a one-pot manner, with the release of CO2 as the only by-product and avoiding the need for external oxidants. This protocol provides a powerful approach for the post stage C-H allylation of indazole-based substrates.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Paulo J. Costa, Frederico F. Martins, Chao Pi, Xiuling Cui, Maria Jose Calhorda
Summary: PdCl2 was found to catalyze the C-H activation of QOs through the formation of a metallacycle or an η(3)-QO complex. Activation at the C8 position resulted in a lower energy barrier compared to activation at the C2 position. The presence of water led to C8-H activation and the formation of 2-quinolinones.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Multidisciplinary
Junwei Huang, Xuelin Yue, Yijie Gao, Yadong Feng, Xiuling Cui
Summary: A mild and efficient method for the synthesis of structurally diverse N/O spiroheterocycles has been developed via Rh(iii)-catalyzed [3+3] cascade spiroannulation of benzoxazines with 1-diazonaphthalen-2(1H)-ones. The desired spirooxazine-pyrans could be obtained in up to 99% yields at room temperature within 30 min. This transformation involves C-H activation, tautomerization, and intramolecular nucleophilic addition in a one-pot manner. In addition, this catalytic system shows high efficiency, atomic economy, wide functional group tolerance, and extremely mild reaction conditions.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Yong Wang, Jingyuan Li, Yanyan Li, Chao Pi, Yangjie Wu, Xiuling Cui
Summary: In this study, a de novo organocatalyzed enantioselective construction of hydantoins from simple urea and glyoxal is reported. It is proposed that a chiral phosphoric acid (CPA) catalyzed [3 + 2] heteroannulation/enantioselective Heyns rearrangement is involved in this transformation. The Heyns rearrangement proceeds smoothly via a proton-transfer process involving an enol intermediate, with CPA serving as a chiral proton-transfer shuttle to control the enantioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(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)
