Article
Chemistry, Physical
Youxiang Jin, Hao Wen, Feiyan Yang, Decai Ding, Chuan Wang
Summary: In this study, a cross-electrophile strategy was successfully applied to synthesize multisubstituted allenes. Nickel-catalyzed reductive cross-coupling between propargyl carbonates and organoiodides provided a method to prepare tri- or tetrasubstituted allenes without the need for pregenerated organometallics. Furthermore, propargyl carbonates were found to be suitable allenylating agents in nickel-catalyzed asymmetric reductive aryl-allenylation, leading to the formation of chiral benzene-fused cyclic compounds with a quaternary allenyl-substituted stereogenic center in a highly enantioselective manner.
Article
Chemistry, Multidisciplinary
Jie Sheng, Hui-Qi Ni, Shan-Xiu Ni, Yan He, Ru Cui, Guang-Xu Liao, Kang-Jie Bian, Bing-Bing Wu, Xi-Sheng Wang
Summary: Monofluorinated alkyl compounds play a significant role in pharmaceuticals, agrochemicals, and materials. This study demonstrates a direct nickel-catalyzed monofluoromethylation of unactivated alkyl halides using a cost-effective industrial raw material, bromofluoromethane, showing high efficiency, mild conditions, and excellent functional-group compatibility. The research establishes a new method for the synthesis of aliphatic fluorides through reductive cross-coupling of alkyl halides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Yue Min, Jie Sheng, Jian-Liang Yu, Shan-Xiu Ni, Guobin Ma, Hegui Gong, Xi-Sheng Wang
Summary: A nickel-catalyzed asymmetric trifluoroalkylation of aryl iodides was described for the first time, demonstrating high efficiency, mild conditions, and excellent functional group tolerance, especially for substrates containing diverse pharmaceutical and bioactive molecules moieties. This strategy provided an efficient and facile way for diversity-oriented synthesis of chiral trifluoromethylated alkanes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Jichao Xiao, John Montgomery
Summary: A simple procedure for the nickel-catalyzed defluorinative alkylation of unactivated aliphatic aldehydes is reported. The protocol exhibits broad substrate scope, mild conditions, and a simple catalytic setup.
Review
Chemistry, Multidisciplinary
Uzma Afzal, Muhammad Bilal, Muhammad Zubair, Nasir Rasool, Syed Adnan Ali Shah, Zainul Amiruddin Zakaria
Summary: Reductive cross-electrophile transformations have become a reliable and durable synthetic technique for specific CAC bond production. The use of inexpensive and abundant electrophiles eliminates the need for organometallic pre-formation and handling. Nickel is a cost-effective and versatile transition metal widely used in stereospecific reductive cross-coupling reactions. This paper reviews the current advancements in nickel catalyzed reductive cross-coupling reactions and their potential application in the synthesis of biologically active molecules.
JOURNAL OF SAUDI CHEMICAL SOCIETY
(2023)
Article
Chemistry, Applied
Kang Wu, Tian-Zhang Wang, Yu-Feng Liang
Summary: This nickel-catalyzed reductive cross coupling reaction allows for the efficient generation of structurally diverse thioesters by activating carboxylic acids with disulfides. The reaction demonstrates broad substrate scope and wide functional group tolerance, making it a convenient and practical tactic for constructing carbon-sulfur bonds.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Yao Deng, Yunyan Meng, Qiongtong Yang, Zixiu Liu, Ruifeng Fan, Jingchao Chen, Baomin Fan
Summary: The enantioselective reductive coupling of oxabenzonorbornadiene with vinyl bromide was developed using earth-abundant nickel catalyst with copper as Lewis acid co-catalyst. The asymmetric reductive coupling is applicable with a wide range of azabenzonorbornadienes and vinyl bromides under nickel/copper co-catalytic system, affording the cis ring-opening vinylation products in good yields with high optical purities. This study enables straightforward stereoselective preparation of chiral 2-vinyl-tetrahydronaphthalens from vinyl halides.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Biao Wang, Tianze Zhang, Li-Jun Xiao, Qi-Lin Zhou
Summary: The addition of MeOLi promotes the ring opening of the aza-nickelacycle intermediate and facilitates hydride transfer from the methoxy group to nickel, enabling the reductive coupling of alkenes with imines. This pathway involving the reductive transformation of saturated aza-nickelcycles allows for highly selective C-C bond formation.
Article
Chemistry, Multidisciplinary
Ming-Xiang You, Pei-Feng Su, Ze-Hui She, Xing-Zhong Shu
Summary: The C-Ge cross-coupling is a promising method for the precise synthesis of organogermanes. This study demonstrates the possibility of converting low-cost and easily available ester groups into organogermanes through cleavage of stable C-O bonds. The coupling of primary, secondary, and even tertiary benzylic pivalates with chlorogermanes is achieved under mild conditions. The scalability of the reaction and the derivatization of the formed benzylgermanes are also demonstrated.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hepan Wang, Xinxuan Li, Tao Xu
Summary: Chiral phosphine-containing skeletons are crucial in various applications including bioactive natural products, pharmaceuticals, chiral catalysts, and ligands. However, the development of convenient and modular methods for accessing chiral allylic phosphorus compounds has remained challenging due to the simultaneous control required for reactivity, enantioselectivity, and stereoselectivity. In this study, a general and modular platform for asymmetric reductive cross-coupling of a-bromophosphonates and vinyl bromides is presented, enabling the synthesis of highly valuable chiral allylic phosphonate products with remarkable yields, enantioselectivities, and stereoselectivities.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Organic
Juan Carlos Nieto-Carmona, Raul San Roman, Elena Bunuel, Diego J. Cardenas
Summary: A Ni-catalyzed cascade cyclization/Negishi-coupling reaction has been developed for the synthesis of pyrrolidines and pyrrolidinones. This method enables the formation of two C-C bonds in a single step and can utilize various nucleophilic reagents.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Kerry-Ann Green, Aaron P. Honeycutt, Sierra R. Ciccone, Kyle A. Grice, Andreas Baur, Jeffrey L. Petersen, Jessica M. Hoover
Summary: Ni-catalyzed C-H functionalization reactions are efficient routes to synthesize various functionalized arenes, but the mechanisms are not well understood. The study reports the catalytic and stoichiometric arylation reactions of a nickel(II) metallacycle. Treatment with silver(I)-aryl complexes leads to facile arylation, indicating a redox transmetalation step. The redox transmetalation step may be applicable to other coupling reactions with silver salts as additives.
Article
Chemistry, Multidisciplinary
Nate W. J. Ang, Lutz Ackermann
Summary: In this research, an efficient and mild electrochemical thiolation method was developed for the synthesis of alkyl sulfides by cross-electrophile coupling of alkyl bromides with bench-stable thiosulfonates. Mechanistic insights into this electrocatalytic thiolation reaction were elucidated through cyclic voltammetry and potentiostatic analysis.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Cui-Tian Wang, Peng-Yu Liang, Ming Li, Bin Wang, Yu-Zhao Wang, Xue-Song Li, Wan-Xu Wei, Xue-Ya Gou, Ya-Nan Ding, Zhe Zhang, Yu-Ke Li, Xue-Yuan Liu, Yong-Min Liang
Summary: The aryl-to-vinyl nickel 1,4-migration (1,4-Ni migration) reaction has been reported for the first time. It involves a tandem reaction that delivers trisubstituted olefins by reductive coupling of alkenyl Ni species with unactivated brominated alkanes. This reaction exhibits mild conditions, high selectivity, and the intermediates do not isomerize.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Dawei Zhang, Xing Gao, Qiao-Qiao Min, Yucheng Gu, Guillaume Berthon, Xingang Zhang
Summary: A nickel-catalyzed cross-coupling reaction of heteroaryl halides with chlorodifluoroacetamides and chlorodifluoroacetate has been developed, which offers an efficient and potential method for synthesizing medicinal compounds.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
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.
Review
Chemistry, Organic
Han-Qiu Zhang, Chu-Xuan Yan, Jian Xiao, Ya-Wen Wang, Yu Peng
Summary: This review discusses the synthetic progress of bioactive 2,7'-cyclolignans, focusing on the chemical synthesis methods like Pd-catalyzed C-H arylation and organocatalysis. The newly developed methods aim to stimulate further development of novel synthetic strategies for natural products with important biological activities.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
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, Multidisciplinary
Jing-Si Cao, Jing Zeng, Jian Xiao, Xiao-Han Wang, Ya-Wen Wang, Yu Peng
Summary: A nickel-catalyzed reductive cyclization was developed to construct the tricyclic core of linoxepin. The generated diastereodivergent acetals can be converted to linoxepin analogs. This strategy facilitates the facile production of several linoxepin analogs.
CHEMICAL COMMUNICATIONS
(2022)