Article
Chemistry, Organic
Paul Wieneck, Hans-Dieter Arndt
Summary: A novel method for C-H cyanation of different pyrans, pyrroles, indoles, and acyclic nucleophilic double bonds using TMSCN, NIS, and Zn(OTf)2 as a catalyst is described. The transformation is conducted under mild conditions tolerating a variety of functional groups. Zn(OTf)2 is likely to serve a dual catalytic role as an activator for TMSCN and for the cyanogen iodide generated in situ. Optimization, the substrate scope, and mechanistic observations are reported. Furthermore, this method is applied in the first total synthesis of the natural product nannozinone B.
Article
Chemistry, Multidisciplinary
Nazarii Sabat, Weiping Zhou, Vincent Gandon, Xavier Guinchard, Guillaume Vincent
Summary: This study reports a method for the direct addition of arenes to the C3 position of unprotected indoles using triflic acid at room temperature. This simple and efficient method allows for the synthesis of biologically relevant 3-arylindolines and 3,3-spiroindolines in high yields.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Ming Zhang, Qingyang Zhou, Heng Luo, Zi-Lu Tang, Xiufang Xu, Xiao-Chen Wang
Summary: Here, we present a method for C3-selective cyanation of pyridines by a tandem process using an in situ generated dihydropyridine and a cyano electrophile. This method is suitable for late-stage functionalization of pyridine drugs. The success of this method relies on the low reduction potential of the electrophile and effective transfer of the nitrile group. Detailed investigation of the reaction mechanism revealed that a combination of electronic and steric factors determines the regioselectivity of reactions involving C2-substituted pyridines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Tai-Jin Cheng, Jun-Jie Chen, Peng Wu, Hui Xu, Hui-Xiong Dai
Summary: A copper-mediated ortho-C-H amination of anilines using oxalamide as the directing group and DMF as the amination reagent is reported in this study. The protocol shows good heterocyclic compatibility and synthetic practicality, with mechanistic experiments suggesting a radical pathway may be involved in the reaction.
Editorial Material
Chemistry, Multidisciplinary
Ahmed Fnaiche, Bianca Bueno, Claire L. McMullin, Alexandre Gagnon
Summary: In this study, we investigated the Barton copper-promoted C3-arylation of indoles using triarylbismuth bis(trifluoroacetates) in detail. Under Barton's conditions, the arylation of unsubstituted 1H-indole gave low yield of C3-arylated indole, along with small amounts of double C2/C3-arylation product and traces of C2 arylation product. On the contrary, the arylation of indoles blocked at the C2 position was highly efficient and provided desired products of C3-arylation in good to excellent yields. The reaction showed simple conditions, good substrate scope, excellent functional group compatibility, and allowed the transfer of electron-neutral or deficient aryl groups. Computational studies proposed a mechanism involving a trifluoroacetate-assisted C-H activation step.
Article
Chemistry, Multidisciplinary
Ahmed Fnaiche, Bianca Bueno, Claire L. McMullin, Alexandre Gagnon
Summary: In this study, we investigated the C3-arylation of indoles using triarylbismuth bis(trifluoroacetates) promoted by Barton's copper. The arylation of unsubstituted 1H-indole under Barton's conditions yielded a low yield of C3-arylated indole, along with some double C2/C3-arylation product and traces of C2 arylation product. On the other hand, the arylation of C2-blocked indoles showed high efficiency and good to excellent yields of the desired C3-arylation products. The reaction demonstrated simple conditions, broad substrate scope, excellent functional group compatibility, and the ability to transfer electron-neutral or deficient aryl groups. Computational studies proposed a mechanism involving trifluoroacetate-assisted C-H activation.
Article
Chemistry, Organic
Jiahui Su, Qiongya Li, Ying Shao, Jiangtao Sun
Summary: An enantioselective cyclopropanation reaction of N-substituted 2-pyridones with diazo compounds has been successfully achieved using a chiral rhodium complex as the catalyst, leading to the formation of chiral cyclopropanes with high enantioselectivities and good yields. Additionally, a novel 1,4-rearrangement of a Boc group from N to C has been discovered under rhodium catalysis when using acceptor-acceptor dimethyl 2-diazomalonate as the carbene precursor.
Review
Chemistry, Organic
Prakash Chandra, Neha Choudhary, Goutam K. Lahiri, Debabrata Maiti, Shaikh M. Mobin
Summary: Earth-abundant transition metal based catalytic materials are essential for clean chemical manufacturing, replacing expensive noble metal based catalytic systems. Copper based catalytic systems are effective in promoting functionalization of organic substrates and organic transformations. Nitriles, as a significant class of nitrogen-containing compounds, have various applications in pharmaceutical and fine chemical industries.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Zhaoliang Xu, Yu Hu, Lei Wang, Mingli Sun, Pinhua Li
Summary: A combined cobalt and photoredox catalysis system was developed for the C8-H alkoxylation of 1-naphthylamine derivatives with alcohols, yielding good product yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xin Zhang, Zonghan Li, Hongshuai Chen, Chaoren Shen, Haihong Wu, Kaiwu Dong
Summary: A parallel paired electrosynthetic method is developed for the first time, which couples the electrocarboxylation of CO2 into ketone, imine, and alkene with alcohol oxidation or oxidative cyanation of amine. Various carboxylic acids as well as aldehyde/ketone or α-nitrile amine were prepared at the cathode and anode respectively in a divided cell. The method demonstrates high atom-economic CO2 utilization, elevated faradaic efficiency (total FE of up to 166%), and broad substrate scope, with potential application in green organic electrosynthesis proven through the synthesis of pharmaceutical intermediates for Naproxen and Ibuprofen.
Article
Chemistry, Organic
Wen-Bin Cao, Jian-Dong Zhang, Meng-Meng Xu, Hua-Wei Liu, Hai-Yan Li, Xiao-Ping Xu, Shun-Jun Ji
Summary: A catalyst-free [1+2+3] cycloaddition/N-N bond cleavage sequential reaction was developed to access spiroindolines with syn-stereoselectivity by utilizing an underexplored reaction mode of C,N-cyclic azomethine imines. Experimental results and DFT calculations identified peroxide and ethereal solvent as triggers for the reaction, initiating hydrogen abstraction and subsequent N-N bond cleavage.
Article
Chemistry, Multidisciplinary
Taochun Zha, Jiehui Rui, Zhihan Zhang, Dongqiang Zhang, Zhirong Yang, Peiyuan Yu, Yingcheng Wang, Fangzhi Peng, Zhihui Shao
Summary: Here we present a Pd-catalyzed asymmetric allenylic alkylation strategy using P-chiral BIBOP-type ligands for the direct functionalization of 1H-indoles. The regioselectivity of this process can be efficiently switched between N1 and C3. N1-alkylated indoles with axial chirality and non-adjacent stereocenter (b) to the nitrogen were obtained in good yields with high enantioselectivity and complete N1-regioselectivity regardless of the electronic properties and substitution patterns of diverse indoles using Cs2CO3 at elevated temperatures in MeCN. Chiral C3-alkylated indoles can also be achieved using K2CO3 at room temperature in CH2Cl2. Notably, a new class of tri-substituted allenylic electrophiles was introduced, which proceeded through different pathways from di-substituted allenylic electrophiles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Souradip Sarkar, Aniruddha Biswas, Sarbojit Das, Bortika Sanyal, Rajkumar Sahoo, Rajarshi Samanta
Summary: A rhodium(III)-catalyzed C4-selective cyanation of indole using N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) as a coupling partner is described. The protocol showed a broad scope and achieved site selectivity by utilizing a weakly coordinating tert-amide group. The photophysical properties of the C4-cyanated indole frameworks were studied.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Aijun Zhou, Zhenlian Wang, Fan Chen, Peng-Cheng Qian, Jiang Cheng
Summary: In this study, a copper-mediated chelation-assisted direct aromatic ortho-C-H cyanation using AIBN as a safe cyanation reagent was developed. The reaction successfully achieved cyanation of substrates including indoles, pyrroles, a carbazole, and a thiophene.
Article
Chemistry, Multidisciplinary
Souradip Sarkar, Aniruddha Biswas, Sarbojit Das, Bortika Sanyal, Rajkumar Sahoo, Rajarshi Samanta
Summary: This study describes a rhodium(III)-catalyzed indole C4-selective cyanation using the bench-stable and user-friendly electrophilic cyanation agent N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) as a coupling partner. The selective site was achieved by utilizing a suitable weakly coordinating tert-amide group. The protocol developed in this study has a wide scope and [Cp*Rh(MeCN)(3)][SbF6](2) was identified as an effective Rh(III) catalyst. The photophysical properties of the C4-cyanated indole frameworks were also investigated.
CHEMICAL COMMUNICATIONS
(2023)
Review
Chemistry, Multidisciplinary
Zhiying Du, Qiqi Qi, Wei Gao, Li Ma, Zhenxian Liu, Ruiming Wang, Jianbin Chen
Summary: Electrochemical organic synthesis shows great potential as an alternative to traditional chemical reactions in constructing heteroatom-heteroatom bonds. By using sustainable electricity as a redox agent, toxic and explosive oxidants and transitional metals can be avoided, resulting in efficient and environmentally friendly reactions.
Article
Chemistry, Multidisciplinary
Li Ma, Xianang Gao, Xin Liu, Xiaojun Gu, Baoying Li, Beibei Mao, Zeyuan Sun, Wei Gao, Xiaofei Jia, Jianbin Chen
Summary: Organic electrosynthesis, as a green and advantageous alternative to traditional synthetic methods, has made remarkable progress in recent years by using sustainable electricity as traceless redox agents. To overcome the issues of over-oxidation/reduction in direct electrolysis, mediated or indirect electrochemical processes have become increasingly important and have improved product selectivity. Heterogeneous catalysts, with their high activity, stability, and recyclability, have received more attention compared to molecular electrocatalysts. In this review, the recent progress in heterogeneous catalysts modified electrodes for organic electrosynthesis is summarized, focusing on structural optimization, electrochemical performance, and reaction mechanisms. Key challenges and future directions in this field are also discussed.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Analytical
Ruiming Chen, Shu Xing, Tingting Hu, Yiming Li, Jianbin Chen, Qingfen Niu, Tianduo Li
Summary: A new ICT type chemosensor DTB with D-pi-A structure has been synthesized and demonstrated to have high sensitivity and specificity for detecting hypochlorite (ClO-). DTB can rapidly detect ClO- through colorimetric and fluorometric dual signaling, and has been successfully applied in various biological samples and environments. This research offers a new idea for developing better-performing chemo/biosensors.
ANALYTICA CHIMICA ACTA
(2023)
Article
Chemistry, Analytical
Ruiming Chen, Tingting Hu, Shu Xing, Tao Wei, Jianbin Chen, Tianduo Li, Qingfen Niu, Zhengyang Zhang, Huijun Ren, Xiaoxu Qin
Summary: Researchers developed a fluorescent sensor PT that can visually distinguish and detect N2H4 and ClO-. It has high sensitivity and fast response time, making it applicable for quantitative detection of N2H4 and ClO- in various samples. The sensor can also visualize the presence of these substances in living plants and cells.
ANALYTICA CHIMICA ACTA
(2023)
Article
Pharmacology & Pharmacy
Rui Sun, Tao Wu, Shu Xing, Sheng Wei, John K. Bielicki, Xuefang Pan, Mingyang Zhou, Jianbin Chen
Summary: In this study, the effects of pure caffeic acid on atherosclerosis and cognitive decline were investigated using the ApoE-/- mice model. The results showed that treatment with caffeic acid significantly reduced atherosclerotic lesions in the aorta and aortic sinus of the mice compared to the control group. Additionally, caffeic acid treatment alleviated cognitive decline and reduced the accumulation of b-amyloid in the hippocampus. These effects were associated with increased HDL-c concentration, upregulated expression of ABCA1 and ABCG1 genes, decreased inflammation, and reduced levels of pro-inflammatory cytokines in the serum.
JOURNAL OF PHARMACOLOGICAL SCIENCES
(2023)
Article
Chemistry, Analytical
Ruiming Chen, Shu Xing, Tingting Hu, Jianbin Chen, Qingfen Niu, Tianduo Li
Summary: Rationally designed and effectively synthesized D-pi-A chemosensor DTA containing bithiophene fluorophore shows high specificity and sensitivity for hypochlorite (ClO-) detection in aqueous media. DTA can be used for qualitative and quantitative visual detection of ClO- in real-time, and also applied in bioimaging and various applications.
SENSORS AND ACTUATORS B-CHEMICAL
(2023)
Article
Chemistry, Physical
Ziqi Liu, Jiaxin Song, Yushuang Zhang, Shuhui Sun, Zhe Kun, Jianbin Chen, Congxia Xie, Xiaofei Jia
Summary: An efficient Rh/PPh3 catalyst was developed for isomerization of 1-alkenes to (E)-2-alkenes, showing high yields and good stereoselectivities. A porous organic polymer supported rhodium catalyst (Rh/POP-PPh3-SO3Na) was synthesized to address catalyst separation and recycling issues, exhibiting high activity, stereoselectivity and recyclability. The olefin isomerization process involved two possible mechanisms, alkyl and allyl mechanisms.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Organic
Yi Lu, Zhirui Liu, Chao Liu, Yunpeng Wu, Lu Li, Siyuan Liu, Hong Wang, Wei Gao, Zhenxian Liu, Jianbin Chen
Summary: An environmentally friendly electrochemical fluorotrifluoromethylation of styrenes was developed, which involves tandem processes of electro-oxidation and radical and nucleophilic addition. Using commercial CF3SO2Na and Et3N•3HF as the sources of CF3 and F, a range of potentially bio-active multi-site F-containing compounds were obtained in moderate to good yields. This catalyst- and oxidant-free fluorotrifluoromethylation strategy offers mild conditions and high step economy features, and the reaction mechanism was investigated using several analytical methods.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Hong Wang, Xiangbin Li, Yi Lu, Lianxuan Wang, Siyuan Liu, Wei Gao, Yonghe Tang, Ling Wang, Liwei Niu, Jianbin Chen
Summary: An electrochemical synthetic strategy for constructing P-(O)-F bonds was developed through the Atherton-Todd reaction. With the promotion of Et4NCl, a series of biologically active phosphoric fluorides were synthesized using commercially available P-(O)-H feedstocks and Et3N center dot 3HF as the F-source. This sustainable fluorination approach features step-economy, is chemical-oxidant- and metal-catalyst-free, and offers low cost and mild conditions. Additionally, cyclic voltammetry and control experiments were conducted to propose a reasonable mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Yuying Wang, Siyuan Liu, Jiangsheng Han, Ling Wang, Jianbin Chen
Summary: Photoelectrochemical cerium catalysis is an emerging and rapidly developing strategy in organic syntheses. By combining energy transfer from light and electricity to cerium and ligand-to-metal charge transfer, a sustainable platform is being constructed, enabling the activation of hard-to-oxidize substrates under mild conditions and broad functional group compatibility.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Siyuan Liu, Yi Lu, Siying Sun, Hong Wang, Wei Gao, Yuying Wang, Xiaofei Jia, Jianbin Chen
Summary: In this study, an electrochemical dehydrogenative homo-/cross-coupling reaction of weakly activated naphthalene was developed without the involvement of exogenous transition metals and oxidants. The electropolymerization of aromatic rings was suppressed due to the interaction between the reactants and the carbon plate anode. A series of binaphthyl and naphthalene-aryl privileged scaffolds were obtained in yields of 28%-90% through homo- or cross-coupling. This C(sp2)-H activation strategy offers atom and step economy, and can be easily scaled up.
GREEN SYNTHESIS AND CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Zhe Shu, Xiu-Xiu Zhao, Zhaohui Zheng, Xueqing Zhang, Yushuang Zhang, Shuhui Sun, Jianbin Chen, Congxia Xie, Bing Yuan, Xiaofei Jia
Summary: The tandem hydroformylation-acetalization of olefins using Rh/BINAPa and ZSM-35(10) co-catalysts has been developed. Various olefins and alcohols showed high performance in terms of regioselectivity (l/b >= 30.5) and catalytic activity (TON of the Rh catalyst up to 4.3 x 10(4)). Control experiments and DFT calculations revealed that hydroformylation occurred outside the molecular sieve, while acetalization took place mainly inside the molecular sieve.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Chen Liang, Zhibin Chen, Xinyue Hu, Shengxia Yu, Zhenlian Wang, Jiang Cheng
Summary: We developed a phosphine-catalyzed ring-opening reaction of cyclopropenones with dicarbonyl compounds as C-nucleophiles, leading to 1,3,3'-tricarbonyl compounds. This transition-metal free procedure features mild and neutral reaction conditions with good atom economy, providing an easy pathway to access 1,3,3'-tricarbonyl derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Food Science & Technology
Tao Wu, Xiaoyu Liu, Zeyuan Sun, Shu Xing, Liwen Han, Xiaobin Li, Xuefang Pan, Jianbin Chen, Mingyang Zhou, Tetiana Derkach, John K. Bielicki
Summary: Phyllanthus emblica fruit may suppress atherosclerosis development by inhibiting macrophage recruitment and foam-cell genesis, reducing vascular cholesterol deposition.
FOOD SCIENCE AND TECHNOLOGY RESEARCH
(2022)
Article
Chemistry, Physical
Jinrong Zhang, Jin Li, Kechao Li, Jinyu Zhao, Zhengyi Yang, Lingbo Zong, Jianbin Chen, Cong-Xia Xie, Xiu-Xiu Zhao, Xiaofei Jia
Summary: Porous organic polymers were synthesized and used as catalysts in hydroformylation reactions. One of the catalysts showed better performance than the others. Two kinds of Rh-H species were identified in the catalyst, with one contributing to high activity and the other to high regioselectivity. DFT calculations and cycle test results indicated that the presence of PPh3 moieties improved the stability of the Rh-H species.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
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)
