Review
Chemistry, Organic
Amina Moutayakine, Anthony J. Burke
Summary: In this review, we discuss the recent advances in the synthesis of medicinally relevant oxygen benzofused heterocycles through the palladium and copper catalyzed C-X activation of haloarene precursors. This transformation has demonstrated remarkable versatility and efficiency, allowing for the construction of diverse scaffolds in a cost-effective manner. The haloarene motif, due to its availability and low cost, has emerged as an exceptional candidate for catalytic reactions leading to medicinally important targets.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sanjay Singh, Sankalan Mondal, Nagaraju Vodnala, Chinmoy Kumar Hazra
Summary: In this study, unsymmetrical polyarylated alkanes were synthesized using a cheap, commercially available Bronsted acid-catalytic system (pTSA center dot H2O)/HFIP. The one-pot three-component approach avoided the use of pyrophoric reagents, metal catalysts, toxic solvents, or Grignard reagents, and showed high greenness in terms of various green metrics. The method was also applied for the synthesis of pharmaceuticals and natural product functionalization.
Article
Chemistry, Applied
Yangyang Wang, Tingting Meng, Shuaisong Su, Limin Han, Ning Zhu, Tiezheng Jia
Summary: Sulfondiimines, an underexplored scaffold in organic chemistry, have been synthesized efficiently through a copper-catalyzed method presented in this study. The synthesis allows the preparation of diversified sulfondiimines with various functional groups, and it was also used to generate an aza-analogue of an EphB4 inhibitor featuring a sulfondiimine-based pharmacophore.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Inorganic & Nuclear
Rahman Hosseinzadeh, Nora Aghili, Mohammad Mavvaji
Summary: Functionalized nanocellulose was used to prepare a heterogeneous copper catalyst, which showed remarkable catalytic efficiency in C-O and C-N cross-coupling reactions. The catalyst could be easily recovered and reused multiple times without significant loss of catalytic activity.
Article
Chemistry, Multidisciplinary
Hai-Jun Zhang, Longrui Chen, Martins S. Oderinde, Jacob T. Edwards, Yu Kawamata, Phil S. Baran
Summary: The formation of aryl-alkyl ether bonds through cross coupling of alcohols with aryl halides using a Ni-catalyzed electrochemical method is a useful and operationally simple strategy with a broad substrate scope. This method does not require strong base or expensive transition metal catalysts, and can be easily scaled up in batch or flow settings. Additionally, e-etherification shows an enhanced substrate scope compared to the mechanistically related photochemical variant.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Xu Liu, Limin Wang, Hao-Yang Wang, Jianwei Han
Summary: In this study, an efficient site-selective O-arylation method for complex arenes involving intramolecular aryl rearrangement is presented. The reaction is facilitated by diaryliodonium salts bearing vicinal trifluoromethanesulfonate (OTf) groups. The procedure starts with selective C-H bond activation of arenes, followed by nucleophilic aromatic substitution (SNAr) to convert them into diaryl ethers. This synthetic method successfully provides complex diaryl ether derivatives, demonstrating its practicality in the diversification of functionalized arenes and pharmaceutical agents.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Linlong Dai, Yuheng Liu, Qing Xu, Meifang Wang, Qiaohong Zhu, Peiyuan Yu, Guofu Zhong, Xiaofei Zeng
Summary: This paper presents a dynamic kinetic resolution method for the synthesis of axially chiral diaryl ethers. By using a Bronsted acid catalyzed atroposelective transfer hydrogenation (ATH) reaction, the desired diaryl ethers could be obtained in moderate to good chemical yields (up to 79%) and high enantioselectivities (up to 95% ee) under standard reaction conditions. These structural motifs are interesting precursors for further transformations and may have potential applications in the synthesis of chiral ligands or catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Matteo Lanzi, Torben Rogge, Tan Sang Truong, K. N. Houk, Joanna Wencel-Delord
Summary: Hypervalent chloranes are rare and poorly explored reagents that possess unique electronic properties. This study reports highly chemo- and regioselective, metal-free, and mild C-C and C-O couplings using these chloranes. Mechanistic studies reveal the unprecedented reactivities and selectivities of these systems and the involvement of aryne intermediates. The synthetic potential of these transformations is demonstrated through post-functionalization of the coupling products obtained from chloranes and phenols under different conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Sayan Shee, Sowmya Shree Ranganathappa, Mahesh S. Gadhave, Romin Gogoi, Akkattu T. Biju
Summary: The N-heterocyclic carbene (NHC)-catalyzed enantioselective esterification of dialdehyde containing diaryl ethers demonstrates the atroposelective synthesis of C-O axially chiral diaryl ethers. The reaction proceeds via a desymmetrization strategy under mild conditions, yielding the corresponding axially chiral diaryl ether atropisomers with good yields and high enantioselectivities. The derivatization of the synthesized product expands the utility of the strategy and allows access to a library of C-O axially chiral compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Muhammad Adnan Bashir, Langyu Tang, Longjie Li, Huaibin Yu, Weijun Yao, Guojiao Wu, Fangrui Zhong
Summary: A formal dual C(sp(2))-H cross-dehydrogenative C-O bond formation method was developed, which can efficiently assemble diversely functionalized diaryl ethers. The reaction proceeds under mild conditions with excellent atom and step economy. In addition, a rare C(sp(2))-O bond formation occurs in this reaction.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Xian-Chao Cui, Hu Zhang, Yi-Ping Wang, Jian-Ping Qu, Yan-Biao Kang
Summary: In this study, we report a new photocatalytic method for the 2- or 4-pyridylation of compounds containing O, N, or S groups, using the organic photoreductant CBZ6 and sulfoxides or sulfides as HAT reagents. This is the first base-free version of the alpha-C-H 2-/4-pyridylation of compounds containing ethers, amines, or thioethers.
Article
Chemistry, Organic
Patrick Cyr, Eve-Marline Joseph-Valcin, Patrick Boissarie, Bruno Simoneau, Anne Marinier
Summary: This study presents a copper-catalyzed method for the N-1-selective arylation of 3-aminoindazoles using readily accessible aryl bromides as coupling partners, facilitating the synthesis of a variety of substituted 3-aminoindazoles. The methodology was also applied to other aminoazoles of interest to the pharmaceutical industry.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Can-Ming Zhu, Rong-Bin Liang, Yonghong Xiao, Wei Zhou, Qing-Xiao Tong, Jian-Ji Zhong
Summary: This study reports a novel approach using commercially available and cheap (Bu4NBr)-Bu-n as a cocatalyst, photoactivated by 4-CzIPN, to selectively activate the alpha-C-H bond of tetrahydrofuran for C-S and C-C cross-couplings. This transition-metal free strategy offers simplicity in operation, mild and environmentally friendly conditions, and a wide range of substrates.
Article
Chemistry, Multidisciplinary
Zhuang Wang, Kaikai Niu, Yuxiu Liu, Hongjian Song, Qingmin Wang
Summary: A mild and convenient protocol for the synthesis of alpha-alkoxy isochroman derivatives has been reported in this study. The electrochemical alpha-C(sp(3))-H/O-H cross-coupling reactions of isochromans and alcohols in the presence of benzoic acid were used, which facilitated the electro-oxidation process and increased the product yield. The desired coupling products were obtained in moderate to high yields.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Yue Jia, Zhihan Zhang, Guo-Ming Yu, Xuan Jiang, Liang-Qiu Lu, Wen-Jing Xiao
Summary: A visible light induced enantioselective deaminative arylation of amino acid derivatives by bifunctional copper catalysis is disclosed. A variety of alpha-aryl-N-phenylamides are prepared with good efficiency and high enantioselectivity. Experimental investigations and theoretical calculations reveal the crucial role of additional phenols in improving catalytic efficiency and enantiocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Jiuxi Chen, Yong Peng, Miaochang Liu, Jinchang Ding, Weike Su, Huayue Wu
ADVANCED SYNTHESIS & CATALYSIS
(2012)
Article
Chemistry, Applied
Jianbin Chen, Bin Liu, Dongfang Liu, Shan Liu, Jiang Cheng
ADVANCED SYNTHESIS & CATALYSIS
(2012)
Article
Chemistry, Applied
Hong-Juan Deng, Yu-Jing Fang, Gao-Wei Chen, Miao-Chang Liu, Hua-Yue Wu, Jiu-Xi Chen
APPLIED ORGANOMETALLIC CHEMISTRY
(2012)
Article
Chemistry, Multidisciplinary
Liang Gaigai, Liu Miaochang, Chen Jiuxi, Ding Jinchang, Gao Wenxia, Wu Huayue
CHINESE JOURNAL OF CHEMISTRY
(2012)
Article
Physics, Multidisciplinary
Chen Jun-Hua, Fan Hong-Yi, Jiang Nian-Quan
Article
Chemistry, Inorganic & Nuclear
Shaojin Gu, Bo Liu, Jiuxi Chen, Huayue Wu, Wanzhi Chen
DALTON TRANSACTIONS
(2012)
Article
Chemistry, Multidisciplinary
Jilei Zhang, Jiuxi Chen, Miaochang Liu, Xingwang Zheng, Jinchang Ding, Huayue Wu
Article
Pharmacology & Pharmacy
Xiepeng Lin, Wenxia Gao, Chenen Li, Jiuxi Chen, Chen Yang, Huayue Wu
INTERNATIONAL JOURNAL OF PHARMACEUTICS
(2012)
Article
Chemistry, Organic
Quan-Sheng Ding, Ji-Lei Zhang, Jiu-Xi Chen, Miao-Chang Liu, Jin-Chang Ding, Hua-Yue Wu
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2012)
Editorial Material
Chemistry, Organic
Jiu-Xi Chen
Article
Chemistry, Organic
Hui Xu, Wanzhi Chen, Jiuxi Chen, Huayue Wu
SYNTHESIS-STUTTGART
(2012)
Article
Chemistry, Organic
Gaigai Liang, Jing Chen, Jiali Chen, Wanmei Li, Jiuxi Chen, Huayue Wu
TETRAHEDRON LETTERS
(2012)
Article
Chemistry, Multidisciplinary
Chuanli Shi, Jinchang Ding, Jun Jiang, Jiuxi Chen, Huayue Wu, Miaochang Liu
JOURNAL OF CHEMICAL RESEARCH
(2012)
Article
Chemistry, Multidisciplinary
Guang-Shu Lv, Fu-Jun Duan, Jin-Chang Ding, Tian-Xing Cheng, Wen-Xia Gao, Jiu-Xi Chen, Hua-Yue Wu
JOURNAL OF CHEMICAL SCIENCES
(2012)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.