Article
Chemistry, Multidisciplinary
Guangwu Sun, Herui Liu, Xiu Wang, Wenbo Zhang, Wenjun Miao, Qinyu Luo, Bing Gao, Jinbo Hu
Summary: In this manuscript, a novel palladium-catalyzed coupling reaction between gem-difluoroalkenes and aryl boronic acids is reported, which yields bioactive indane-type ketones with an all-carbon alpha-quaternary center. The mechanism involves a water-induced defluorination and cross-coupling cascade pathway, supported by characterization and stoichiometric reactions of the key intermediates RCF2PdII. The use of vinyl difluoromethylene motif as an in situ carbonyl precursor is unprecedented in transition-metal-catalyzed coupling reactions, and it is expected to spark broad interest in ketone synthesis, fluoroalkene functionalization, and design of new synthetic protocols based on the unique reactivity of difluoroalkyl palladium(II) species.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Hao Chen, Cui Wei, Guang-Li Pang, Cui Liang, Dong-Liang Mo, Xiao-Pan Ma
Summary: A new type of quinoxaline-derived tridentate N,N,O-ligand was synthesized and successfully applied in the synthesis of N-vinyl cinnamaldehyde nitrones with high Z-selectivity and good yields.
Article
Chemistry, Organic
Xiaoshen Ma, Charles S. Yeung
Summary: Our study focused on achieving C(sp(2))-C(sp(3)) coupling reactions using 2,2-difluorobicyclo[1.1.1]pentane (BCP-F-2) building blocks. Through comparison of reactivities between BCP and BCP-F-2 analogues, we found that the Barluenga coupling reaction showed promising results, expanding the potential applications of BCP-F-2 in organic chemistry and medicinal chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yaxin Wang, Jianyou Zhao, Tianjiao Qiao, Jian Zhang, Gong Chen
Summary: This study presents an efficient method for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants, involving electron, proton, and hydrogen atom transfers. By selectively reducing carbonyl groups of substrates to alcohols, pinacols, or methylene groups with carefully chosen solvents and acidic additives, products with indolizidine scaffolds can be obtained. The N-3/HN3 cycle as a hydrogen atom shuttle is critical for the reduction of carbonyl groups to methylene groups.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kaikai Niu, Yanke Hao, Lingyun Song, Yuxiu Liu, Qingmin Wang
Summary: The radical cleavage of C-B bonds for C-H functionalization is synthetically appealing but challenging. A mild electro-oxidative method was reported for efficient C-H alkylation of quinoxalin-2(1H)-ones using radical addition reactions of alkyl boronic acids, esters, and alkyl trifluoroborates to afford C-C coupled products.
Article
Chemistry, Organic
Xing Wu, Guojian Ma, Xichao Peng, Zuozhou Ning, Zirun Lin, Xiaoguang Chen, Yu Tang, Pengju Feng
Summary: This study demonstrates a mild and general protocol for the photoredox initiated oxo-azolation of gem-difluoroalkenes, providing a facile access to synthetically useful azolated difluoroacetonarenes with potential applications in drug and functional materials development. The reaction tolerates a wide range of functional groups and involves a photoredox initiated, active oxygen participated single electron transfer pathway. Furthermore, the reaction solvent can be easily recovered and reused with the same efficiency.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Jing Zhao, Jiuxi Chen, Qing Xu, Huan Li
Summary: This synthetic method uses arylboronic acids and aldehydes or ketones to generate benzoxaboroles in the presence of a Bronsted acid, simplifying starting materials and reducing reaction steps. It is also applicable with acetals and ketals, showing a wide substrate scope and high practicability.
Article
Engineering, Chemical
Zhenming Qi, Ziyin Li, Xiaosai Hu, Shiwen Liu, Yuanyu Ge
Summary: This study successfully solved the nanoparticle agglomeration issue by encapsulating Cu2O micro/nanoparticles into ACF, which showed excellent recycling performance during catalytic reactions with high product yield even after multiple cycles.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
(2021)
Article
Chemistry, Organic
Sufal Paul, Piyush Kumar Verma, Anubhab Kashyap, Rahul Mondal, K. Geetharani
Summary: A new method has been developed for sequentially gem-thioborylating readily available aldehydes through cobalt-catalyzed diboration reaction. The N-heterocyclic carbene (NHC)-cobalt complex serves as a catalyst for the diboration of aldehydes to generate alpha-oxyl boronic esters, which react with lithium thiolates to form a tetracoordinate boronate species undergoing 1,2-metalate rearrangement in the presence of trifluoroacetic anhydride. The stepwise functionalization of the boryl and thiol moiety of the products enriches the chemical toolbox of diverse organic synthesis.
Article
Chemistry, Organic
Satoshi Kishida, Misaki Takano, Takuya Sekiya, Yutaka Ukaji, Kohei Endo
Summary: This paper presents a synthetic method for the synthesis of 1,2,4,5-tetraarylbenzene derivatives using cyclopropenes as starting materials. Through Lewis acid-mediated dimerization, cyclopropenes are transformed into tricyclo[3.1.0.02,4]hexane derivatives. The subsequent thermal ring-opening reaction under solvent-free conditions yields 1,4-cyclohexadienes bearing quaternary carbons. The novel Br2-mediated oxidative rearrangement of 1,4-cyclohexadienes results in the formation of 1,2,4,5-tetraarylbenzene derivatives with high to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(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, Multidisciplinary
Qiqiang Xie, Guangbin Dong
Summary: The Matteson-type reactions have gained increasing interest in organic synthesis, but current tactics mainly focus on carbon chains. In this study, we report the development of the oxa-Matteson reaction, which allows oxygen and carbenoid insertions into alkyl- and arylboronates, leading to the synthesis of boron-substituted ethers. The method demonstrates its utility in the preparation of functional ethers, asymmetric synthesis, and programmable construction of polyethers.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Mengqi Luo, Shibo Zhu, Chengcheng Shi, Yunlong Du, Chao Yang, Lin Guo, Wujiong Xia
Summary: We report a vinyl radical-mediated 1,5-hydrogen atom transfer (1,5-HAT) strategy for remote C(sp(3))-H functionalization reaction, including cyanation, oxidation, and etherification. This method efficiently constructs structurally diverse gamma-cyano, gamma-carbonyl, and gamma-oxygenated alkenes with excellent stereoselectivity.
Article
Chemistry, Multidisciplinary
Yoichi Dokai, Kodai Saito, Tohru Yamada
Summary: A Lewis acid-mediated decarboxylative 1,2-rearrangement reaction of cyclic carbonates was developed, showing contrasting selectivity to that of corresponding 1,2-diols.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Jian-Fei Bai, Jianbo Tang, Xiaolong Gao, Zhi-Jiang Jiang, Bencan Tang, Jia Chen, Zhanghua Gao
Summary: We report an acid-catalyzed formal cycloaddition and dehydrative substitution reaction of tertiary propargylic alcohols and heteroareneboronic acids. The regioselectivity of the reaction is determined by the properties of the substituents on the alkynyl moiety, allowing for the selective construction of fused hetero-cycles, tetrasubstituted allenes, or 1,3-dienes. This transition-metal-free protocol exhibits high efficiency with a wide range of substrates in up to 89% yield.
Article
Chemistry, Applied
Xiao-Ting Qin, Ning Zou, Xiao-Ling Cheng, Cui Liang, Dong-Liang Mo
Summary: A variety of chiral nine-membered N-heterocycles were prepared in moderate to good yields with high diastereoselectivity through a silver(I)-catalyzed reaction. Experimental studies showed that the silver catalyst promoted the cycloaddition and rearrangement process, and controlled the stereochemistry of the products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Wang Wang, Nan-Ying Chen, Pei-Sen Zou, Li Pang, Dong-Liang Mo, Cheng-Xue Pan, Gui-Fa Su
Summary: A variety of pseudorutaecarpine derivatives were successfully prepared in good to excellent yields through a gold(I)-catalyzed selective cyclization and N-alkynyl quinazolinone-tethered indoles. These derivatives exhibit anti-inflammatory activity, and the reaction conditions are mild with a broad substrate scope.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
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
Wang Wang, Pei-Sen Zou, Li Pang, Yao Lei, Zi-Yi Huang, Nan-Ying Chen, Dong-Liang Mo, Cheng-Xue Pan, Gui-Fa Su
Summary: In this study, functionalized spiroindolenine-3,3'-pyrrolo[2,1-b]quinazolinones with good anti-inflammatory activity were synthesized through a gold(I)-catalyzed reaction. The reaction showed a broad substrate scope and easy scalability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Lu Lei, Pei-Sen Zou, Zhi-Xin Wang, Cui Liang, Cheng Hou, Dong-Liang Mo
Summary: A regioselective Heck reaction catalyzed by a P-containing palladacycle was described, which affords 2-aryl-2,5-dihydrofurans and 2-aryl-2,3-dihydrofurans in good yields from 2,3-dihydrofuran with diaryliodonium salts and aryl iodides, respectively. Mechanistic studies and DFT calculations revealed the chemoselectivity and regioselectivity-determining step of this reaction.
Article
Chemistry, Applied
Hao Yuan, Dong-Liu Lu, Cui Liang, Dong-Liang Mo
Summary: Various spirooxindole-benzo[d]oxazoles and dihydrobenzofurans were successfully synthesized via transition metal-free [3 + 2] cycloaddition and selective rearrangement. The substituent on the N-vinyl group of the nitrone was found to control the [1,3]- or [3,3]-rearrangement of the cycloadduct due to steric effects. This method demonstrates broad substrate scope, good functional group tolerance, controllable rearrangement, and diverse oxindole scaffolds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Ning Zou, Zhang-Wei Liu, Gong-Gui Yan, Ying-Chun Wang, Cui Liang, Dong-Liang Mo
Summary: A DBU-controlled 6π-azaelectrocyclization was used to prepare 6-alkyl pyridine N-oxides in yields ranging from 24% to 82%. Mechanistic studies showed that DBU played a significant role in the formation of 6-alkyl pyridine N-oxides, acting as a base and a carrier of hydrogen sources.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Hong-Yan Bi, Qing-Yan Wu, Xiao-Mei Zhou, Hui-Juan Xu, Cui Liang, Dong-Liang Mo, Xiao-Pan Ma
Summary: By employing N-hydroxypyridin-2-ones as the oxygen and nitrogen sources, arylboronic acids were difunctionalized successfully to prepare various N-(2-hydroxyaryl)pyridin-2-ones in good yields through a copper(II)-catalyzed Chan-Lam reaction and subsequent BF3 promoted selective 1,3-rearrangement. Mechanistic studies revealed that the selectivity of the 1,3-rearrangement is controlled by the formation of the key aryloxypyridinium salt. The obtained products can be easily converted to various useful pyridin-2-one scaffolds.
Article
Chemistry, Organic
Cui Wei, Zhou Zhou, Guang-Li Pang, Cui Liang, Dong-Liang Mo
Summary: A variety of oxazabicyclo[4.2.1]nonanone derivatives were synthesized in good yields through a cascade reaction, involving several steps, and a single-pot reaction. Mechanistic studies revealed the reaction pathway and the role of the catalyst in achieving the desired products.
Article
Chemistry, Organic
Hao Chen, Cui Wei, Guang-Li Pang, Cui Liang, Dong-Liang Mo, Xiao-Pan Ma
Summary: A new type of quinoxaline-derived tridentate N,N,O-ligand was synthesized and successfully applied in the synthesis of N-vinyl cinnamaldehyde nitrones with high Z-selectivity and good yields.
Article
Chemistry, Organic
Dong-Liu Lu, Yi-Yun Yao, Yu-Feng Liang, Cui Liang, Lu Lei, Lu Ma, Dong-Liang Mo
Summary: A variety of tetrahydro-5H-indolo[2,3-b]quinolines were efficiently synthesized through a copper(II)-catalyzed cascade reaction. This reaction involved double 1,4-additions and sequential intramolecular cyclization, and demonstrated broad substrate scope and scalability.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Pei-Pei Xu, Su-Ge Xin, Xue Li, Cui Liang, Dong-Liang Mo
Summary: We developed a copper(II)-catalyzed [3+2] cycloaddition reaction between N-aryl-alpha,beta-unsaturated nitrones and disubstituted allenoates to prepare a variety of [1,3]oxazino[3,2-a]indolines and dihydropyrido[1,2-a]indolines in moderate to excellent yields. Mechanistic studies revealed the kinetic preference for [1,3]oxazino[3,2-a]indoline and the thermodynamic preference for dihydropyrido[1,2-a]indoline. The reaction can be easily scaled up and chiral dihydropyrido[1,2-a]indoline can be obtained using a chiral auxiliary. The method demonstrates broad substrate scope, good functional group tolerance, and high diastereoselectivity, making it highly significant.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Li Pang, Shu-Jun Fang, Pei-Sen Zou, Wang Wang, Jun-Cheng Su, Xiao-Qing Liu, Cheng-Xue Pan, Dong-Liang Mo, Gui-Fa Su
Summary: We report a transition-metal free [4 + 4] cycloaddition reaction between 2-alkynyl quinazolines and aza-ortho-quinone methides (ao-QMs) generated from 2-(bromomethyl)anilines, leading to the synthesis of various [1,5]diazocino[2,1-b]quinazolinones in good to excellent yields under mild reaction conditions and short reaction time. Furthermore, a [1,5]diazocino[2,1-b]quinazolinone derived from estrone was easily prepared in 30% total yield over five steps, and showed significant inhibition of nitric oxide generation in LPS-stimulated RAW264.7 cells. This method offers advantages such as broad substrate scope, gram-scale preparation, and simple purification operation without flash column chromatography.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Organic
Qin Xiaoting, Zou Ning, Nong Caimei, Mo Dongliang
Summary: This review summarizes the novel synthetic strategies of nine-membered N-heterocycles and their applications in the synthesis of natural products and pharmaceutically active molecules containing nine-membered ring scaffold in recent years.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Wang Wang, Pei-Sen Zou, Li Pang, Cheng-Xue Pan, Dong-Liang Mo, Gui-Fa Su
Summary: Quinazolinone and its derivatives are important structural units in pharmaceuticals and medicinal chemistry, exhibiting a wide range of biological and pharmacological activities. The synthesis strategies for 2,3-fused quinazolinone derivatives have made significant advances in recent years.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
