Article
Chemistry, Multidisciplinary
Takeshi Fujita, Yutaro Kobayashi, Ikko Takahashi, Ryutaro Morioka, Tomohiro Ichitsuka, Junji Ichikawa
Summary: Nickel-catalyzed reductive cross-coupling of allylic difluorides with aryl iodides was successfully achieved, leading to the synthesis of a series of gamma-arylated monofluoroalkenes with moderate to high yields and high Z-selectivities. Mechanistic studies indicated that the cleavage of C-I bonds in aryl iodides and C-F bonds in allylic difluorides occurred through oxidative addition and beta-fluorine elimination, respectively.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Shi Tang, Zhen-Hua Xu, Ting Liu, Shuo-Wen Wang, Jian Yu, Jian Liu, Yu Hong, Shi-Lu Chen, Jin He, Jin-Heng Li
Summary: A novel nickel-catalyzed radical relay has been reported for the remote cross-electrophile coupling of amino acid esters with aryl bromides, enabling the formation of two new C(sp(3))-C(sp(2)) bonds with broad substrate scope and excellent diastereoselectivity. Mechanistically, this cascade reaction combines powerful catalytic cycles involving cross-electrophile coupling and radical aryl migration, resulting in the generation of C(sp(3))-centered radical intermediates and the transformation of transient alkyl radical into a robust alpha-aminoalkyl radical.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Hao Liu, Zi-Rong Gong, Meng-Ling Lin, Wen Luo, Yan-Jun Xu, Lin Dong
Summary: A one-pot approach using maleimide derivatives as dienophiles has been developed for intramolecular C-H activation/C-O coupling, dearomatization, and [4+2] cycloaddition of BINOL units. This tandem catalytic system efficiently produces a range of functionalized bridged polycyclic products in a step-economical manner, significantly expanding the modification methods for BINOL skeletons.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Aleksandra Blocka, Jakub Ostapko, Wojciech Chaladaj
Summary: For the first time, a cascade reaction involving a 5-exo-dig intramolecular nucleophilic addition of an enamine to a terminal alkyne followed by cross coupling has been demonstrated. This reaction allows for the stereoselective formation of two new C-C bonds using a single Pd-complex capable of catalyzing two mechanistically diverse transformations. Mechanistic investigations revealed that cyclization, relying on the facile displacement of OTf weakly bound to the Pd-center by the alkyne, is the rate limiting step.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Shaoqun Zhu, Yingjie Pan, Yue Sun, Xiaoyan Hong, Xiaoyun Chen, Ying Han, Chaoguo Yan, Yaocheng Shi, Hong Hou
Summary: In this study, a copper-catalyzed bromo-cyanomethylative cyclization of 1,6-enynes is demonstrated. The treatment of 2-bromoacetonitrile with CuI enables the generation of alkyl radicals, triggering a radical addition/cyclization/bromination sequence that yields functionalized heterocycles with vinyl C-Br bonds in good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Saikat Maiti, Joon Ho Rhlee
Summary: Stereoselective dicarbofunctionalization of terminal aryl alkynes has been achieved through reductive Ni-catalysis, utilizing alkyl iodide and aryl iodide as electrophilic coupling partners to accomplish exclusive regioselective and anti-addition selective alkylarylation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Wenjun Miao, Chuanfa Ni, Pan Xiao, Rulong Jia, Wei Zhang, Jinbo Hu
Summary: This novel nickel-catalyzed reductive cross-coupling reaction allows the formation of C(sp(2))-C(sp(2)) bonds through selective C(sp(2))-S bond cleavage, showcasing the new reactivity of 2-PySO2CF2H reagent. The use of readily available nickel catalyst and sulfones as coupling partners enables facile access to biaryls under mild reaction conditions without pregeneration of arylmetal reagents.
Article
Chemistry, Organic
Guifang Chen, Bo Xu
Summary: We have developed a C-O cross-coupling reaction between (hetero)aryliodides and silver carboxylates using a Au-I/Au-III catalytic cycle. This transformation shows exclusive chemoselectivity and is insensitive to moisture and air. It is applicable to both aromatic and aliphatic (including primary, secondary, and tertiary) silver carboxylates, and works well in both intermolecular and intramolecular settings. Importantly, high yields are obtained regardless of the electronic effect and steric hindrance of the substrates.
Article
Chemistry, Organic
Hao Xu, Cai-Yu He, Bo-Jie Huo, Jia-Wen Jing, Chengping Miao, Weidong Rao, Xue-Qiang Chu, Xiaocong Zhou, Zhi-Liang Shen
Summary: In this study, a cross-electrophile coupling of aryl thiols with aryl bromides was reported, where C-S bond activation occurred instead of S-H bond cleavage, leading to the formation of thioethers as the major products. The reaction proceeded effectively with a nickel catalyst, magnesium turnings, and lithium chloride in THF at room temperature, and a variety of structurally diverse biaryls were obtained in moderate to good yields.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Linlin Ding, Yue Zhao, Hongjian Lu, Zhuangzhi Shi, Minyan Wang
Summary: For the first time, a catalytic enantioselective propargyl-aryl cross-coupling between two electrophiles was achieved in a stereoconvergent manner. The potential utility of this conversion is demonstrated in the facile construction of stereoenriched bioactive molecule derivatives and medicinal compounds based on the diversity of acetylenic chemistry. Detailed experimental studies have revealed the key mechanistic features of this transformation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Jing-Ao Ren, Xue Chen, Chao Gui, Chengping Miao, Xue-Qiang Chu, Hao Xu, Xiaocong Zhou, Mengtao Ma, Zhi-Liang Shen
Summary: A step-economical and operationally simple nickel-catalyzed cross-electrophile coupling reaction was developed, enabling the coupling of aryl phosphates and aryl bromides through C-O bond cleavage without the use of moisture-labile and uncommonly available organometallics. The reaction proceeded smoothly in the presence of magnesium turnings and lithium chloride in THF solvent, providing moderate to good yields of biaryls with reasonable functionality tolerance.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Pei-Feng Su, Ke Wang, Xuejing Peng, Xiaobo Pang, Peng Guo, Xing-Zhong Shu
Summary: A novel cross-electrophile C-Ge coupling reaction has been reported, showing the potential of obtaining diverse organogermanes under mild conditions, with applications demonstrated in the synthesis and derivatization of complex molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Gang Li, Liu Yang, Jian-Jun Liu, Wei Zhang, Rui Cao, Chao Wang, Zunting Zhang, Jianliang Xiao, Dong Xue
Summary: This study demonstrates a photochemical C-N coupling of aryl halides with nitroarenes for the first time, catalyzed by a Ni-II complex in the absence of any external photosensitizer. The method provides a step-economic extension to the widely used Buchwald-Hartwig C-N coupling reaction and tolerates coupling partners with steric-congestion and functional groups sensitive to bases and nucleophiles. Mechanistic studies suggest the reaction proceeds via the addition of an aryl radical, generated from a Ni-I/Ni-III cycle, to a nitrosoarene intermediate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Fengxiang Zhu, Pengpeng Yin, Pengbo Zhang
Summary: A convenient four-component reaction has been developed to directly transform aryl iodides with alkyl halides into aromatic esters and diesters via palladium-catalyzed carbonylation with water as solvent. The method exhibits moderate to good yields and broad functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Yun-Zhao Wang, Zhen-Hua Wang, Inbal L. L. Eshel, Bing Sun, Dong Liu, Yu-Cheng Gu, Anat Milo, Tian-Sheng Mei
Summary: The efficiency of the enantioselective nickel-catalyzed reductive cross-coupling of aryl aziridines with aryl iodides is improved through an electrochemical method. Beta-phenethylamines are produced in good to excellent enantioselectivity with broad functional group tolerance. The electroreduction-mediated turnover of the nickel catalyst is credited for the high efficiency of this method.
NATURE COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Xin Guo, Chang-Xiang Liu, Yuan Lu, Ya-Wen Wang, Yu Peng
Summary: A novel two-site chemodosimeter (SWJT-4) based on fluorescein skeleton was designed and synthesized to detect diethyl chlorophosphate (DCP). It acts as a turn-on fluorescent probe for DCP in aqueous solution, exhibiting good selectivity and obvious color change. The two oxime groups of SWJT-4 initiate different reactions with DCP, forming a cyano group and an isoxazole ring, respectively.
Article
Biochemistry & Molecular Biology
Zhiyuan Zhuang, Zhenbiao Luo, Sichen Yao, Yawen Wang, Yu Peng
Summary: A short synthesis of racemic Sacidumlignan B was achieved for the first time, involving a formal reductive coupling and a subsequent Friedel-Crafts cyclization to construct the dihydronaphthalene skeleton of this natural product.
Article
Biochemistry & Molecular Biology
Chang-Xiang Liu, Shu-Yuan Xiao, Xiu-Lin Gong, Xi Zhu, Ya-Wen Wang, Yu Peng
Summary: A novel near-infrared (NIR) fluorescent probe, SWJT-9, was designed and synthesized for the detection of hypochlorite anion (ClO-), showing excellent NIR fluorescence response with a color change under visible light. SWJT-9 demonstrated high selectivity, low detection limit (24.7 nM), and rapid detection (within 2 minutes) for ClO-. The detection mechanism of SWJT-9 on ClO- was confirmed using H-1 NMR, MS spectrum, and density functional theory (DFT) calculations.
Article
Chemistry, Organic
Yang Zhou, Hai Xu, Qing-Xiu Li, Zong-Rui Hou, Ya-Wen Wang, Yu Peng
Summary: Based on the AIE and TICT mechanisms, a fluorescent probe SWJT-12 was designed for the detection of ClO- by using the C equivalent to N bond as a reactive group. The synthesized probe can react with ClO- in a high aqueous phase, showing a large Stokes shift (144 nm) and low biological toxicity. Its limit of detection was calculated to be 0.28 μM. Furthermore, SWJT-12 was successfully used for ratiometric imaging of the exogenous hypochlorite anion in living cells.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Lin-Yuan Zhang, Li-Jun Xu, Ya-Wen Wang, Yu Peng
Summary: In this study, a ferrocene derivative was synthesized in a one-step reaction from benzotriazole-1-yl-oxytripyrrolidino-phosphonium hexafluorophosphate and ferrocenecarboxylic acid. The structure of the synthesized compound was determined accurately using H-1 and C-13 NMR, and further confirmed by X-ray diffraction analysis of a single crystal.
Article
Biochemistry & Molecular Biology
Xue-Shuang Yu, Mao-Mei Zhu, Rui Zuo, Yu Peng, Ya-Wen Wang
Summary: A new turn-on probe, SWJT-20, based on isophorone fluorophore was synthesized for the detection of nerve agent mimic diethyl chlorophosphite (DCP). SWJT-20 exhibited rapid response to DCP within 2 s using UV-Vis or fluorescent spectra, accompanied by a noticeable change in solution color under visible or UV light, observable with the naked eye. The detection limit of SWJT-20 for DCP was as low as 8.3 nM, surpassing most reported fluorescent probes for DCP detection. Additionally, SWJT-20 enabled quantitative measurement of DCP through ratio changes in absorption spectra (A(427)/A(645)). Furthermore, facile paper sensors were developed based on SWJT-20, allowing colorimetric/fluorometric responses for visual detection. Notably, this probe also detected DCP vapor through gas diffusion experiments.
Article
Chemistry, Analytical
Wei Du, Xiu-Lin Gong, Yang Tian, Xi Zhu, Yu Peng, Ya-Wen Wang
Summary: In this study, a coumarin derivative, SWJT-14, was synthesized as a fluorescence probe to effectively distinguish Cys, Hcy, and GSH in aqueous solutions. The probe showed a lower detection limit for Cys, Hcy, and GSH compared to biothiols in cells. It reacted with biothiols to generate different products with distinct conjugated structures, and fluorescence and UV-Vis spectra were used for differentiation. The detection mechanism was confirmed by MS. SWJT-14 was successfully utilized in cellular experiments for the detection of both endogenous and exogenous biothiols.
Article
Chemistry, Organic
Hai Xu, Long-Zhou Xu, Rui-Ping Huai, Chen Zhang, Sheng-Nan Suo, Ya-Qian Li, Yu Peng, Ya-Wen Wang
Summary: Inspired by the synthetic method of benzoxazine derivatives and our previous research, a fluorescent probe (SWJT-6) was designed for formaldehyde detection based on the cyclization reaction. The synthetic SWJT-6 showed excellent colorimetric and ratiometric response to formaldehyde, and could be perfectly used as test strips to detect formaldehyde. In addition, SWJT-6 has been successfully applied in bioimaging of intracellular and lysosomal formaldehyde in both HeLa cells and zebrafish.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Xue-Shuang Yu, Rui Zuo, Ming-Ye Shuai, Xu Feng, Yu Peng, Ya-Wen Wang
Summary: A novel ratiometric and colorimetric probe (SWJT-16) based on the isophorone skeleton was synthesized for the detection of diethyl chlorophosphite (DCP), a mimic of nerve agent. SWJT-16 showed a significant emission shift (??(em) = 174 nm) and a remarkable color change from blue to yellow under visible light upon nucleophilic substitution reaction with DCP in DMF. These changes occurred within 6 seconds, faster than most reported ratiometric fluorescent probes for DCP. Furthermore, SWJT-16 was effectively used to monitor gaseous DCP.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Min Peng, Quan-Rong Du, Xue Yao, Chun-Ni Li, Yang Tian, Yu Peng, Ya-Wen Wang
Summary: A simple fluorescein derivative was synthesized as a fluorescent probe for detecting malondialdehyde (MDA). The probe achieved ring-opening of fluorescein and formation of a benzohydrazide derivative through a synergistic reaction. It exhibited high sensitivity and selectivity for MDA detection, and could quickly and visually detect MDA within 60 s using UV-vis and fluorescent modes. Moreover, the probe showed excellent performance in imaging MDA in living cells and bacteria.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Nai-Jie Lin, Huan Wu, Jing Peng, Shu-Han Yang, Rui Tan, Yu Peng, Ya-Wen Wang
Summary: A novel ratiometric probe SWJT-10 based on isophorone derivatives was successfully designed and synthesized for the detection of formaldehyde (FA). This probe exhibited significant ratiometric fluorescence response to FA in aqueous solution, with a blue shift from NIR (680 nm) to yellow light region (600 nm). It showed excellent selectivity, high sensitivity, and rapid response to FA (less than 5 s) due to a new recognition mechanism. Furthermore, SWJT-10 has been successfully applied for monitoring FA in living cells and zebrafish.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Yu-Qing Zhang, Zhi-Nan Kang, Jing-Jie Ming, Sheng-Nan Suo, Jia-Ling Kang, Hai Xu, Ya-Wen Wang, Yu Peng
Summary: A new fluorescent probe has been developed for relay detection of hypochlorite ions and viscosity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hai Xu, Chen Zhang, Yu-Qing Zhang, Sheng-Nan Suo, Ya-Wen Wang, Yu Peng
Summary: A novel red-NIR probe (SWJT-8) has been developed for detecting acrolein using the Michael addition reaction. SWJT-8 exhibits unique advantages such as colorimetric discrimination, high selectivity, and the fastest response. This probe has been successfully applied to detect intracellular acrolein.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Zhen-Biao Luo, Ya-Wen Wang, Yu Peng
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Bao-Jun Wang, Rui-Juan Liu, Jianguo Fang, Ya-Wen Wang, Yu Peng
CHEMICAL COMMUNICATIONS
(2019)
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)
