Article
Chemistry, Organic
Xin Chen, Yangchun Xin, Zhi-Wei Zhao, Yu-Jian Hou, Xiang-Xiang Wang, Wen-Jin Xia, Ya-Min Li
Summary: A novel decarboxylative oxyacyloxylation of propiolic acids has been developed, allowing for efficient access to alkynyl-containing alpha-acyloxy ketones from readily available starting materials with significant functional group tolerance. The reaction mechanism was proposed based on mechanistic studies, along with the oxacyloxylation of terminal alkynes and aliphatic propiolic acids.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Li-Qiu Liu, Jiu-Ling Li, Ying-Chun Wang, Heng-Shan Wang
Summary: A rapid and efficient method for hydroxy or alkoxy-selenation of internal alkenes and chalcones using NFSI as the oxidizing agent is presented. The reaction features broad substrate scope and high regioselectivity, with an electrophilic mechanism proposed for the transformation.
RESULTS IN CHEMISTRY
(2021)
Article
Chemistry, Organic
Bo Jin, Ariamala Gopalsamy, Bo Peng, Li Sha, Sharon Tentarelli, Lakshmaiah Gingipalli
Summary: A photoredox-catalyzed decarboxylative addition of N-substituted acetic acids to aldehydes was developed for the synthesis of secondary alcohols. The successful implementation of this methodology relies on the use of protic solvents. This strategy allows the formation of a novel C-C bond between aldehydes and weakly nucleophilic and medicinally relevant heteroaryls such as indoles, pyrroles, indazoles, and azaindoles.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Danupat Beukeaw, Sirilata Yotphan
Summary: The copper-catalyzed decarboxylative cycloaddition reaction has been reported for the synthesis of 1,4-disubstituted-1,2,3-triazoles. This method offers advantages such as excellent selectivity, high yields, wide substrate scope, and potential applications in synthetic chemistry.
Article
Chemistry, Multidisciplinary
Cen Zhou, Xiaozhou Huang, Yaqing Hu, Junyan Wu, Ying Zheng, Xiao Zhang
Summary: In this study, a catalyst-free approach for the decarboxylative amination of glycine derivatives with azo compounds under visible-light irradiation was reported, leading to the efficient synthesis of a range of important aminals under mild reaction conditions.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Han Ding, Ningjie Yan, Peng Wang, Ni Song, Qikai Sun, Tiantian Li, Ming Li
Summary: An efficient protocol for organophotocatalytic synthesis of reverse glycosyl fluorides (RGFs) has been established using 9-mesityl-10-methyl-acridinium (Mes-Acr(+))-mediated oxidative decarboxylative fluorination of uronic acids. Both pentofuranoid and hexopyranoid uronic acids can serve as viable substrates for this transformation, and a wide range of functional groups are tolerated. The potential of this reaction is demonstrated by the convenient synthesis of RGF-type nucleosides, particularly those with a unique l-lyxo-configuration, thereby providing a novel method to expand the chemical space of nucleosides widely used in drug discovery and development.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Xiangtai Meng, Hehua Xu, Yu Zheng, Jinyue Luo, Shenlin Huang
Summary: A new method has been developed for the synthesis of carbonyl compounds from aliphatic carboxylic acids through electrochemical decarboxylative oxygenation, which features excellent substrate compatibility and high yields of ketones, aldehydes, and amides.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Organic
Yudai Shinkawa, Toshiki Furutani, Takumi Ikeda, Mugen Yamawaki, Toshio Morita, Yasuharu Yoshimi
Summary: The side-chain functionalization of aspartic/glutamic acid derivatives was achieved through photoinduced decarboxylation using organic two-molecule photoredox catalysts without racemization under mild conditions. A facile process involving the preparation of substrates and photoinduced decarboxylative radical additions provides easy access to the linked amino acids with carbohydrates and amino acids at the side chain.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Samira Noori, Ramin Ghorbani-Vaghei
Summary: The present study presents a practical and safe cross-coupling strategy for synthesizing biaryls via the decarboxylation of aryl carboxylic acids. A new catalyst, BF@Propyl/Tris/Pd, was used in this method. The catalyst's structural and morphological characteristics were analyzed using FT-IR, EDX, XRD, TGA, and SEM. This catalyst system demonstrates good stability, excellent workup, and reusability, making it a recyclable heterogeneous catalyst that can be easily separated from the reaction medium.
Article
Chemistry, Multidisciplinary
Kai Yang, Yukang Wang, Sanzhong Luo, Niankai Fu
Summary: In this study, we developed an electrophotochemical metal-catalyzed protocol for direct asymmetric decarboxylative cyanation of aliphatic carboxylic acids. By utilizing the synergistic merging of electrophotochemical cerium catalysis and asymmetric electrochemical copper catalysis, mild reaction conditions were achieved for the formation and utilization of carbon-centered radicals. This environmentally benign method smoothly converts a diverse array of arylacetic acids into the corresponding alkyl nitriles in good yields and enantioselectivities without using chemical oxidants or pre-functionalization of the acid substrates and can be readily scaled up.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
David M. Kitcatt, Simon Nicolle, Ai-Lan Lee
Summary: This review summarizes the recent progress on using carboxylic acids directly as convenient radical precursors for the formation of carbon-carbon bonds.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Artem Tsymbal, Lorenzo Delarue Bizzini, David W. C. MacMillan
Summary: In this study, a dual photo/nickel catalytic manifold was described, which includes a complementary sequence involving free radical generation, radical sorting via selective binding to a Ni(II) center, and bimolecular homolytic substitution (S(H)2) at a high-valent nickel-alkyl complex. This catalytic manifold enables the elusive cross-coupling of diverse aliphatic carboxylic acids to generate valuable C(sp(3))-C(sp(3))-products. The discovery provides important insights for addressing the long-standing challenge in fragment coupling chemistry.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Viet D. Nguyen, Graham C. Haug, Samuel G. Greco, Ramon Trevino, Guna B. Karki, Hadi D. Arman, Oleg V. Larionov
Summary: A direct decarboxylative sulfinylation reaction was developed, enabling the conversion of carboxylic acids to sulfoxides. This reaction improves the structural diversity of synthetically accessible sulfoxides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Ebbin Joseph, Ian Smith, Jon A. Tunge
Summary: The selective incorporation of fluorine-containing groups adjacent to sterically hindered alkyl groups remains a challenge, but the cobalt-catalyzed method allows for the facile construction of difluoroalkylated products and late-stage functionalization of molecules of biological relevance.
Article
Chemistry, Physical
Huanhuan Li, Sabry H. H. Younes, Shaohang Chen, Peigao Duan, Chengsen Cui, Ron Wever, Wuyuan Zhang, Frank Hollmann
Summary: In this study, we report the chemoenzymatic bromodecarboxylation (Hunsdiecker-type) of alpha,ss-unsaturated carboxylic acids using a highly stable chloroperoxidase. The generated hypobromite from H2O2 and bromide reacts spontaneously with a broad range of unsaturated carboxylic acids, yielding the corresponding vinyl bromide products. Selectivity issues, caused by the undesired addition of water to the intermediate bromonium ion, were effectively solved by manipulating the reaction medium. The obtained vinyl bromides can serve as versatile starting materials for various cross-coupling and pericyclic reactions.
Article
Chemistry, Multidisciplinary
Shengbo Ge, Xiangmeng Chen, Dongli Li, Zhenling Liu, Hui Ouyang, Wanxi Peng, Zhongfeng Zhang
ARABIAN JOURNAL OF CHEMISTRY
(2018)
Article
Chemistry, Applied
Ming Cao, Yi-Lin Fang, Ying-Chun Wang, Xiao-Juan Xu, Zhi-Wei Xi, Shi Tang
ACS COMBINATORIAL SCIENCE
(2020)
Article
Chemistry, Medicinal
Wei-Wei Ni, Hai-Lian Fang, Ya-Xi Ye, Wei-Yi Li, Chu-Ping Yuan, Dong-Dong Li, Shi-Jia Mao, Su-E Li, Qi-Hui Zhu, Hui Ouyang, Zhu-Ping Xiao, Hai-Liang Zhu
FUTURE MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Medicinal
Wei-Wei Ni, Hai-Lian Fang, Ya-Xi Ye, Wei-Yi Li, Li Liu, Zi-Juan Fu, Dawalamu, Wen-Yan Zhu, Ke Li, Fang Li, Xia Zou, Hui Ouyang, Zhu-Ping Xiao, Hai-Liang Zhu
Summary: A series of N-monosubstituted aroylthioureas were designed and synthesized as urease inhibitors. The compounds showed potent inhibition against urease, with low cytotoxicity to mammalian cells, and have the potential to be developed as therapeutics against infections caused by urease-containing pathogens.
MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Mei-Ling Liu, Wei-Yi Li, Hai-Lian Fang, Ya-Xi Ye, Su-Ya Li, Wan-Qing Song, Zhu-Ping Xiao, Hui Ouyang, Hai-Liang Zhu
Summary: The study demonstrated that the synthesized disulfides have significant inhibitory activity against urease and Helicobacter pylori, with low cytotoxicity, indicating potential for therapeutic use in treating H. pylori infections.
Article
Chemistry, Organic
Wei-Li Chen, Zhang-Wei Liu, Ying-Chun Wang, Xiao-Pan Ma, Dong-Liang Mo
Summary: Functionalized sulfonium ylides can be prepared with high yields through MnSO4-promoted S-O bond cleavage. The MnSO4 catalyst also promotes the [1,3] rearrangement of the S-O bond. The obtained product can be easily obtained through recrystallization and can be converted to new sulfonium ylides, which can undergo cycloaddition with an alkyne to form a trisubstituted furan scaffold.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Li-Qiu Liu, Yi-Ling Fang, Jun-Xu Lin, Ying-Chun Wang
Summary: A convenient four-component reaction using a natural abundant copper/air (O-2) catalyst system has been developed to synthesize benzo[4,5]imidazo[2,1-c][1,2,4]selenadiazol-3-imine derivatives. This highly efficient method allows for the construction of multiple bonds in a single step with only water as the byproduct.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yong-Zhou Pan, Qiang Xia, Jin-Xiu Zhu, Ying-Chun Wang, Ying Liang, Hengshan Wang, Hai-Tao Tang, Ying-Ming Pan
Summary: This article presents a method for synthesizing 2-oxazolidinones using CO2 and allylic amines, while preserving the unsaturated double bonds. The method also shows applicability in the synthesis of six-membered heterocycles and allows for subsequent structural modification.
Article
Chemistry, Organic
Zhi-Wei Xi, Yan He, Li-Qiu Liu, Ying-Chun Wang, Hui-Ying Zeng
Summary: Under the catalysis of both Pd(dppf)Cl2 and Cu(OAc)2, a three-component domino reaction of thioamides, benzyl isocyanide, and water resulted in novel 1,2,4-thiadiazolidin-3-one cyclic compounds. In contrast, the same reaction with tertiary alkylisonitriles in the presence of rare earth metal salt [La(OTf)3] produced (E)-N-(1,2-diamino-2-thioxoethylidene)benzamide open chain products. This divergent reaction enabled the formation of five (N-S, C-S, C-O, and two C-N) or four (C-S, C-N, C-O, and C-C) new chemical bonds. Mechanism studies revealed that the oxygen atom in the product was derived from water.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhang Zhang, Ying-Chun Wang, Hai-Tao Tang, Ying-Ming Pan, Xiu-Jin Meng
Summary: Describes an electrocatalytic ring-opening dihydroalkoxylation method for the synthesis of N-aryl maleimides with alcohols, under metal- and oxidant-free conditions. This electrochemical process involves anodic single-electron transfer oxidation, cathodic radical reduction, rearrangement-ring cleavage, and nucleophilic addition cascade. The use of tetrabutylammonium bromide as a redox catalyst and an efficient supporting electrolyte provides a practical and environmentally friendly route to ring-opening difunctionalization products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Qian Wang, Cheng-Hao Xu, Ying-Chun Wang, Ying-Ming Pan, Wen-Gui Duan, Hai-Tao Tang
Summary: A convenient and practical strategy for the synthesis of carbamo(dithioperoxo)thioates has been developed through the dehydrogenation coupling of thiols and amines and the insertion of CS2. This environmentally friendly method has a broad substrate scope and can be used to produce a series of bioactive compounds. It has potential applications in the preparation of antifilarial activity compounds using an electrochemical continuous flow reactor.
Article
Chemistry, Organic
Zhi-Wei Xi, Yan He, Li-Qiu Liu, Ying-Chun Wang
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Organic
Ming Cao, Qing-Hu Teng, Zhi-Wei Xi, Li-Qiu Liu, Ren-Yong Gu, Ying-Chun Wang
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Materials Science, Paper & Wood
Hui Ouyang, Zhenling Liu, Lishu Wang, Wanxi Peng, Heping Deng, Muhammad Aqeel Ashraf
Article
Chemistry, Multidisciplinary
Xuemei Liu, Chaonan Cui, Shuoshuo Wei, Jinyu Han, Xinli Zhu, Qingfeng Ge, Hua Wang
Summary: This study presents a new strategy for designing efficient photocatalysts that can convert CO2 into hydrocarbons by utilizing synergistic catalytic sites. The findings provide a solution for the selective photocatalytic reduction of CO2 to CH4.
Article
Chemistry, Multidisciplinary
Chengxian Hu, Dan Wang, Lu Wang, Ying Fu, Zhengyin Du
Summary: A novel one-pot, three-component reaction conducted under electrochemical conditions was studied. The reaction involved 2-aminothiophenols, aldehydes, and malononitrile, using TBABF4 as an electrolyte and CuI as a catalyst. The proposed reaction mechanism suggested that CuI served as an electron relay. This method offers simplified operation, high atom economy, and mild reaction conditions.
Article
Chemistry, Multidisciplinary
Zhi Yang, Yu Chen, Linxi Wan, Yuxiao Li, Dan Chen, Jianlin Tao, Pei Tang, Fen-Er Chen
Summary: A highly enantioselective method for the complete hydrogenation of pyrimidinium salts using Ir/(S,S)-f-Binaphane complex as the catalyst was developed. This method provides easy access to fully saturated chiral hexahydropyrimidines, which are prevalent in many bioactive molecules. The reactions exhibit high yields and enantioselectivities under mild reaction conditions without additives. Successful application of this methodology in a continuous flow fashion further extends its practical utility.
Article
Chemistry, Multidisciplinary
Tina Jeoh, Jennifer Danger Nill, Wujun Zhao, Sankar Raju Narayanasamy, Liang Chen, Hoi-Ying N. Holman
Summary: In this study, the enzymatic hydrolysis of cellulose was investigated using real-time infrared spectromicroscopy. The spatial heterogeneity of cellulose was found to impact the hydrolysis kinetics. Hydration affected cellulose ordering, and Cel7A preferentially removed less extensively hydrogen bonded cellulose.
Article
Chemistry, Multidisciplinary
Tiphaine Richard, Walid Abdallah, Xavier Trivelli, Mathieu Sauthier, Clement Dumont
Summary: An effective method of grafting functionalities onto lignin based on glycerol carbonate has been developed using an efficient nickel-catalysed telomerisation reaction. This method allows lignin to have new reactive functions and reduces the glass transition temperatures of modified lignins, thereby expanding the application range of lignin-based resins.
Article
Chemistry, Multidisciplinary
Jing Qi, Xiyan Wang, Gan Wang, Srinivas Reddy Dubbaka, Patrick ONeill, Hwee Ting Ang, Jie Wu
Summary: This study presents a green and environmentally friendly approach for the synthesis of imides using electrocatalytic oxidation with H2O as the oxygen source. The method eliminates the need for toxic or expensive oxidants and achieves high yields under mild reaction conditions. It shows broad substrate compatibility and potential for industrial applications.
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang
Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.
Article
Chemistry, Multidisciplinary
Juho Antti Sirvio, Idamaria Romakkaniemi, Juha Ahola, Svitlana Filonenko, Juha P. Heiskanen, Ari Ammala
Summary: This article discusses the method of using supramolecular interaction between an aromatic hydrogen bond donor and lignin to achieve rapid delignification of softwood at low temperatures.
Article
Chemistry, Multidisciplinary
Yunyan Meng, Chunxiang Pan, Na Liu, Hongjiang Li, Zixiu Liu, Yao Deng, Zixiang Wei, Jianbin Xu, Baomin Fan
Summary: A novel visible light-driven synthesis method for 2,3-diamines has been developed, which has mild conditions, avoids the use of metal reagents, and can synthesize diamines and diols in one pot.
Article
Chemistry, Multidisciplinary
Mingqing Huang, Haiyang Huang, Mengyao You, Xinxin Zhang, Longgen Sun, Chao Chen, Zhichao Mei, Ruchun Yang, Qiang Xiao
Summary: A direct air-oxidized strategy for the synthesis of benzo[b]phosphole oxides was developed in this study. Arylphosphine oxides were transformed into phosphinoyl radicals, which were further combined with various alkynes to achieve the desired products. DFT calculations revealed the mechanism of phosphinoyl radical formation.
Article
Chemistry, Multidisciplinary
Anwei Wang, Jiayin Huang, Chunsheng Zhao, Yu Fan, Junfeng Qian, Qun Chen, Mingyang He, Weiyou Zhou
Summary: This study demonstrates an innovative strategy for the aerobic oxidation of C(sp(3))-H bonds using gamma-valerolactone. By optimizing the reaction conditions and utilizing specific catalysts, efficient oxidation of C(sp(3))-H bonds is achieved with good chemoselectivity in certain cases.
Article
Chemistry, Multidisciplinary
Shun Li, Likai Tong, Zhijian Peng, Bo Zhang, Xiuli Fu
Summary: Sulfide compounds show promise as electrocatalysts for water splitting, but their performance is limited by factors such as limited active sites and hindered substance transport. This study successfully prepared a high-entropy sulfide (ZnCoMnFeAlMg)(9)S-8, which reduced grain size and increased specific surface area, enabling the realization of a dual-functional catalyst with multiple catalytic sites. High entropy also modulated the electronic properties of sulfides, reducing the potential energy barrier for hydrolysis. This research introduces a new approach for functionalizing high entropy nanomaterials and improves the performance of water splitting catalysts.
