Article
Chemistry, Multidisciplinary
Qiaoli Li, Lanting Xu, Dawei Ma
Summary: Direct N-arylation of sulfonamides using a combination of copper and oxalamides (or 4-hydroxypicolinamides) as catalysts is an efficient method. It allows for a wide range of reactions between sulfonamides and (hetero)aryl bromides, and even works well with primary sulfonamides and (hetero)aryl chlorides under the catalysis of Cu2O and a 4-hydroxypicolinamide.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Runqing Zhu, Qianqian Sun, Jing Li, Luohao Li, Qinghe Gao, Yakun Wang, Lizhen Fang
Summary: Selective hydroxylation of alkyl aryl ethers has been established using a ruthenium(ii) catalyst, hypervalent iodine(iii), and trifluoroacetic anhydride via a radical mechanism. This method is tolerant of a wide range of substrates and provides a facile and efficient way to synthesize clinical drugs on a gram scale.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Travis J. DeLano, Sara E. Dibrell, Caitlin R. Lacker, Adam R. Pancoast, Kelsey E. Poremba, Leah Cleary, Matthew S. Sigman, Sarah E. Reisman
Summary: The study reports an asymmetric reductive cross-coupling reaction with good enantioselectivity using nickel-catalysis and a chiral BiOX ligand to synthesize alpha-arylesters under mild conditions. The reaction shows good yields and enantioselectivities, tolerates a wide range of functional groups, and the resulting products can be used to prepare pharmaceutically-relevant chiral building blocks. Additionally, a multivariate linear regression model was developed to quantify the influence of the alpha-chloroester substrate and ligand on enantioselectivity.
Article
Chemistry, Multidisciplinary
Weiqi Liu, Xinghao Jin, Dawei Ma
Summary: The requirement of higher reaction temperatures for SNAr reaction between thiols and less reactive electron-poor aryl halides has led to the development of metal- and photo-catalyzed methods. In this study, the SNAr reaction between thiols and most electron-poor aryl halides was found to occur at RT-60°C using K2CO3 and DMAc. Additionally, two oxalic diamide ligands were identified to enable Cu-catalyzed coupling reactions with low catalytic loadings for unreactive (hetero)aryl halides, offering a promising approach for preparing (hetero)aryl thioethers.
Article
Chemistry, Physical
Dao Peng, Yu Zhang, Xiao-Qing Liu, Hang Shang, Gang Lin, Hong-Ying Jin, Xue-Fen Liu, Ran He, Ye-Han Shang, Yin-Hua Xu, Shu-Ping Luo
Summary: A series of new highly active and reusable copper phthalocyanine derivatives have been researched and developed as catalysts for the hydroxylation of (hetero)aryl halides. Among them, perfluorinated copper phthalocyanine (CuPcF16) showed the highest activity with excellent yields for aryl iodide, aryl bromides, and aryl chlorides. The catalyst can be recycled up to 6 times without significant loss in catalytic activity.
MOLECULAR CATALYSIS
(2022)
Article
Chemistry, Applied
Tomoya Sakaguchi, Tomohiro Shibata, Yusuke Fukuda, Aya Tazawa, Yasuhiro Uozumi, Yoshimasa Matsumura, Osamu Shimomura, Atsushi Ohtaka
Summary: Additive screening was performed for the copper-catalyzed hydroxylation reaction of aryl iodides. Polyethylene glycol (PEG)-200 was found to be the most effective additive, while longer chain PEGs, other alcohols, and oxygen-containing compounds decreased the reaction efficiency. The reaction proceeded smoothly under milder conditions compared to previous reports. A reusable system could be developed using polystyrene-stabilized Cu nanoparticles as the catalyst.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Chao Fang, Bangguo Wei, Dawei Ma
Summary: Some 4-hydroxy-picolinic acid derived amides were found to be more efficient ligands for Cu-catalyzed coupling of (hetero)aryl halides with secondary phosphine oxides and phosphites. Only 3-5 mol% CuI and ligands were needed to complete the coupling of a number of (hetero)aryl bromides and iodides in 10-20 hours at 120 degrees Celsius.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ying Chen, Lanting Xu, Yongwen Jiang, Dawei Ma
Summary: The combination of copper salts and oxalic diamides enables the synthesis of α-(hetero)aryl nitriles via one-pot decarboxylation under mild conditions. The method demonstrates a broad substrate scope and compatibility with various functionalities and heteroaryls.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Giuseppe Dilauro, Francesco Messa, Fabio Bona, Serena Perrone, Antonio Salomone
Summary: A simple cobalt complex, Co(phen)Cl₂, has been found to be a highly efficient and cost-effective precatalyst for various cross-coupling reactions involving aromatic and aliphatic organoaluminum reagents with aryl, heteroaryl, and alkyl bromides. New C(sp²)-C(sp²) and C(sp²)-C(sp³) bonds can be formed in good to excellent yields and high chemoselectivity under mild reaction conditions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Zhenlei Zou, Heyin Li, Mengjun Huang, Weigang Zhang, Sanjun Zhi, Yi Wang, Yi Pan
Summary: This work presents a general strategy for metal-catalyzed cross-coupling of fluoroalkyl radicals with aryl halides under electrochemical conditions. By using paired electrolysis, the contradiction between anodic oxidation of fluoroalkyl sulfinates and cathodic reduction of low-valent nickel catalysts can be effectively addressed, thus allowing for direct introduction of fluorinated functionalities into aromatic systems.
Article
Chemistry, Organic
Jing Liu, Yisa Xiao, Jian Hao, Qilong Shen
Summary: A copper-catalyzed trifluoromethylation of (hetero)-arylboronic acid pinacol esters with YlideFluor was described, allowing the preparation of trifluoromethylated (hetero)arenes. The reaction conditions are mild and compatible with a broad range of functional groups. The application of this method for trifluoromethylation of drug and OLED molecules was demonstrated.
Article
Chemistry, Multidisciplinary
Yunhui Feng, Hang Luo, Fangnian Yu, Qian Liao, Luqing Lin
Summary: Here, we present a visible-light-promoted single nickel catalysis for achieving various C-N couplings of aryl chlorides/bromides and diverse N-nucleophiles using sodium iodide as the activator. The single nickel catalyst plays a dual role in halogen exchange and C-N coupling, which are crucial for obtaining the desired coupling products. This catalytic process eliminates the need for an exogenous photocatalyst and offers a sustainable and efficient approach for mild C-N coupling. Experimental studies, along with UV-vis and NMR analyses, demonstrate that the halogen exchange between both Ni-II and Ni-III-halide complexes and the iodide anion is a significant process in the formation of coupling products.
Article
Chemistry, Organic
Subhajit Bhunia, Subhadip De, Dawei Ma
Summary: BPMO is an appropriate promoter for the Cu-catalyzed N-arylation reaction at room temperature, showing excellent chemoselectivity between aryl iodides and aryl bromides, and good tolerance towards diverse functional groups.
Article
Chemistry, Organic
Suman Pal, Marine Cotard, Baptiste Gerardin, Christophe Hoarau, Cedric Schneider
Summary: The study introduces a regioselective Cu-catalyzed oxidative allylic C(sp(3))-H arylation by radical relay, utilizing a wide range of heteroaryl boronic acids and inexpensive, readily available olefins. Unlike traditional methods, this approach does not require prefunctionalized alkenes and uses cheap, nontoxic Cu2O.
Article
Chemistry, Organic
Xinmiao Huang, Ling Tang, Zhiyong Song, Shuangshuang Jiang, Xianmao Liu, Ming Ma, Bo Chen, Yuanhong Ma
Summary: A nickel catalysis system has been developed for the desulfonylative C(sp(2))-C(sp(2)) reductive cross-coupling reactions of aryl sulfone derivatives with aryl bromides to form diverse biaryl compounds. The isolated and confirmed Ar-Ni(II)-SO(2)CF3 complex with a phosphine ligand through oxidative addition of aryl sulfone to Ni(0) species provides solid evidence for understanding the C(Ar)-SO2 bond activation and reaction mechanism.
Article
Chemistry, Applied
Xueying Zhou, Yaling Xu, Caihong Wang, Ge Wu
Summary: A copper-catalyzed vinylamination of S-alkylisothiouronium salts with maleimide and organic amines was reported, assisted by FeCl3. This reaction enables the preparation of structurally diverse aminoalkylthiolated maleimides, which can be applied to late-stage modification of pharmaceuticals. By using prepared S-trideuteromethyl isothiouronium iodide, the SCD3 functional group can be introduced into the maleimide skeleton. Preliminary mechanistic investigation indicates that FeCl3 is crucial for the reaction by triggering S-alkylisothiouronium salts.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Engineering, Environmental
Mengzhu Wang, Feiyang Li, Yunxiang Lei, Fuming Xiao, Miaochang Liu, Shujuan Liu, Xiaobo Huang, Huayue Wu, Qiang Zhao
Summary: By designing and synthesizing novel ORTP materials, the regulation of excitation-dependent luminescence colors has been achieved, showing great potential for advanced applications.
CHEMICAL ENGINEERING JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Ge Wu, Xueying Zhou, Caihong Wang
Summary: A novel and efficient method for decarboxylative alkynylselenation of indoles using Se powder and propiolic acids as catalyst has been developed. This method avoids the use of prefabricated arylselenation reagent and over-seleniumation issues and enriches the chemistry of selenium powder. Furthermore, this reaction can be extended to pyrrole, and its practical utility has been demonstrated in gram-scale synthesis and late-stage indolylselenation of Clofibrate-derived propiolic acid.
CHINESE CHEMICAL LETTERS
(2022)
Article
Engineering, Environmental
Nannan Liu, Yanyan Pan, Yunxiang Lei, Miaochang Liu, Chengdong Peng, Zhengxu Cai, Guomin Shen, Huayue Wu, Xiaobo Huang, Yuping Dong
Summary: In this study, diphenyl sulfoxide was used as the host, and 1,3-diphenylbenzofuro[2,3-c]pyridine was designed as the guest to construct a new phosphorescence doped system. The addition of water, phenol, benzoic acid, and phenylboronic acid as the third component improved the phosphorescence performance. The phosphorescence quantum yields and lifetimes were significantly increased.
CHEMICAL ENGINEERING JOURNAL
(2022)
Article
Chemistry, Physical
Yan Guo, Kaijun Chen, Zechen Hu, Yunxiang Lei, Xiaoqing Liu, Miaochang Liu, Zhengxu Cai, Jiawen Xiao, Huayue Wu, Xiaobo Huang
Summary: This study focuses on the construction of multicomponent doped systems for the development of phosphorescence materials. By selecting benzophenone as the host and phenylquinoline isomers as the guests, and introducing seven different metal ions as the third component, the authors successfully construct a three-component doped system. The results show that the introduction of Ag+ and Cd2+ can significantly increase the emission intensity, while the introduction of Al3+, Ga3+, and In3+ can prolong the emission wavelength, and Cu2+, Ga3+, and In3+ can extend the phosphorescence lifetime.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Organic
Wei Chen, Wanzhi Chen, Miaochang Liu, Huayue Wu
Summary: The palladium-catalyzed Suzuki-Miyaura cross-couplings of nitroarenes and heteroarylboronate esters has been developed, leading to the synthesis of various heterobiaryl compounds. The practicality of this approach is demonstrated through the synthesis of druglike molecules.
Article
Chemistry, Applied
Jia Li, Wenliang Zhang, Yu-An Li, Ge Wu, Xu Zhang
Summary: A meaningful copper-catalyzed oxidative alkylamination reaction has been developed for the synthesis of 3-carbo-4-amino maleimides. This reaction exhibits excellent compatibility with polyfunctional organic amines and inactivated alkanes, and employs a simple and efficient catalytic system.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Li-Guo Lu, Jun-Hua Chen, Xiao-Bo Huang, Miao-Chang Liu, Yun-Bing Zhou, Hua-Yue Wu
Summary: The Pd-catalyzed selective ring opening reaction of cyclopropenones with vinyl epoxides allows for the synthesis of a wide range of conjugated alkadienyl carboxylates in good yield and excellent regioselectivity. This study demonstrates the new application of zwitterionic pi-allyl palladium intermediates in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Jingjing Wang, Yaling Xu, Luya Chen, Yunfei Ma, Ge Wu
Summary: The nucleophilic substitution of organohalides with alkylamines is a key reaction in synthetic chemistry. However, the resulting halide anions are often wasted and not fully utilized. In this study, we present a halogen recycling strategy for aminohalogenation reactions with maleimides and alkylamines, demonstrating excellent generality and compatibility with various functional groups.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Wenting Wang, Lin Zhao, Hui Wu, Youqing He, Ge Wu
Summary: A metal-free oxidative trideuteromethylthiolation of alkenes using CD3SSO3Na as an oxidant has been developed. The aminotrideuteromethylthiolation of a three-component reaction could be easily achieved in the presence of a cobalt catalyst. The divergent trideuteromethylthiolation of alkenes, readily available trideuteromethylthiolation reagent, and versatile synthetic strategy enable late-stage modification of drug molecules.
Article
Chemistry, Organic
Jingjing Wang, Lin Zhao, Yafei Zhang, Peisen Zheng, Peng Zou, Ge Wu
Summary: In this paper, the unprecedented copper-catalyzed aminoalkylation of maleimides using alkyltin fluoride as an alkylating reagent through cleavage of the C-Sn bond via a radical pathway is reported. The standout features of this reaction include excellent functional group tolerance, the use of O-2 as a green oxidant, and late-stage modification of some drug intermediates.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Hui Wu, Youqing He, Kai Sun, Yaling Xu, Wenting Wang, Ge Wu
Summary: A method for iodine(iii)-mediated dehydroaromatization of cyclohexanones with primary amines and CD3SSO3Na has been developed, providing direct access to ortho-SCD3 anilines with the formation of C-N and C-S bonds. Detailed mechanism studies indicate that hypervalent iodine(iii) plays dual roles as an efficient mediator and an oxidant, and the continuously generated alpha-acetoxylated ketones and alpha-SCD3 ketones are the key intermediates in the current three-component reactions. The present transformations demonstrate excellent chemo-selectivity and are applicable for late-stage modification of numerous pharmaceuticals.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Hui Wu, Lin Zhao, Wenting Wang, Yining Yu, Ge Wu
Summary: This paper describes a cascade reaction of cyclohexanones with primary amines and sodium sulfinates, which provides a novel method for the synthesis of o-sulfanylanilines. Preliminary mechanistic studies indicate that the reaction starts with the reductive ortho-thiolation of cyclic ketones with sulfinates, followed by sequential condensation and dehydrogenative aromatization.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yitian Jiang, Miaochang Liu, Mengzhu Wang, Yunxiang Lei, Qiuping Ding, Huayue Wu, Xiaobo Huang
Summary: Two novel 2,7-naphthyridine derivatives, with twisted molecular conformations, were unexpectedly synthesized through different ring-closing mechanisms. These derivatives display phosphorescence, thermally activated delayed fluorescence, and high contrast solid-state acidochromism due to their special chemical structures.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Yaling Xu, Xueying Zhou, Luya Chen, Yunfei Ma, Ge Wu
Summary: The copper-catalyzed radical multi-component coupling enables the rapid synthesis of a library of aminophosphinoylated maleimides. This method is applicable to clinical drug molecules containing sulfonamide and arylamine functional groups, allowing access to sterically congested products. It shows good functional group tolerance and can be used on a wide range of substrates.
ORGANIC CHEMISTRY FRONTIERS
(2022)
