Article
Chemistry, Organic
Na-Na Ma, Jing-Ao Ren, Xiang Liu, Xue-Qiang Chu, Weidong Rao, Zhi-Liang Shen
Summary: The direct cross-couplings of aryl sulfonium salts with aryl halides using nickel as a reaction catalyst were successfully achieved. The reactions proceeded efficiently via C-S bond activation at ambient temperature, providing moderate to good yields, potentially serving as an attractive alternative to conventional cross-coupling reactions.
Article
Chemistry, Organic
Weiqiang Chen, Hui-Jing Li, Yun-Fei Cheng, Yan-Chao Wu
Summary: A C2-arylation reaction of N-acyl pyrroles using Pd(PPh3)(4) as a catalyst in combination with Ag2CO3 under air has been developed for the first time. This method provides a straightforward approach to the synthesis of valuable arylated pyrroles with good substrate tolerance and moderate to good yields under standard conditions. Interestingly, substrates with a thiophene or furan ring were found to be more reactive than pyrrole in the present catalytic system.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Wen-Xin Li, Bo-Wen Yang, Xuan Ying, Zhuo-Wen Zhang, Xue-Qiang Chu, Xiaocong Zhou, Mengtao Ma, Zhi-Liang Shen
Summary: The direct cross-coupling of diaryl sulfoxides with aryl bromides via C-S bond cleavage was achieved using nickel(II) as the catalyst, 1,2-bis(diphenylphosphino)ethane (dppe) as the ligand, and magnesium turnings as the reducing metal in THF. This reaction showed a wide range of substrates and could be used for gram-scale synthesis. The one-pot reaction is operationally simple and economically efficient.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dejiang Zhang, Zhi Xu, Ting Tang, Liyuan Le, Cairong Wang, Nobuaki Kambe, Renhua Qiu
Summary: In this study, a general method for the synthesis of unsymmetric diarylmethanes from (hetero)aryl methylhalides and Sb-aryl stibines is described. The protocol has a broad substrate scope and good functional group tolerance. Gram-scale synthesis of drug molecules and their derivatives was efficiently achieved using this method.
Article
Chemistry, Multidisciplinary
Muhammad Asif Iqbal, Le Lu, Hina Mehmood, Ruimao Hua
Summary: This study reports a Cs2CO3-promoted cross-coupling reaction of arenes with cyano-/nitro-substituted aryl halides in DMSO to afford biaryls in the absence of ligands. The cyano/nitro groups in biaryls are shown to be useful for further transformations. Additionally, the formation of dibenzofurans from reactions between arenes and 1-bromo-2-iodobenzene is reported. A radical mechanism for the formation of biaryls is proposed based on control experiments and theoretical studies.
Article
Chemistry, Multidisciplinary
Sergio Bonesi, Stefano Protti, Maurizio Fagnoni
Summary: Aryl sulfonates and phosphates exhibit different photochemical behaviours in polar and nonpolar media, with photostability observed in nonpolar solvents and homolytic or heterolytic fragmentation in polar solvents depending on the leaving group and substituents on the aromatic ring.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Subramani Kumaran, Kanniyappan Parthasarathy
Summary: An efficient Rh(III)-catalyzed cross-dehydrogenative coupling of N-pyridinylindoles with benzo[b]thiophene 1,1-dioxides has been developed via directing-group-assisted C-H activation, forming a new C-C bond from two inert C-H bonds in a one-pot reaction. The synthesized compounds exhibit compatibility with various functional groups and their emission properties have been explored.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jin-Ming Xie, Yun-Long Zhu, Yan-Ming Fu, Cheng-Feng Zhu, Lan-Jun Cheng, Yang-En You, Xiang Wu, You-Gui Li
Summary: We described a new method for the direct assembly of alpha-(3-indolyl)ketones through the cascade reaction of 2-alkynyl aryl azides with enecarbamates, in which the in situ generated alpha-imino gold carbene intermediate was trapped by enecarbamate to achieve umpolung reactivity of indole at the 3-position.
Article
Chemistry, Organic
Li-Dong Shao, Yang Chen, Mei Wang, Nan Xiao, Zhi-Jun Zhang, Dashan Li, Rong-Tao Li
Summary: A mild Pd-catalyzed method for direct gamma-C(sp(3))-arylation of unactivated beta-alkoxy cyclohexenones is reported. The method is well tolerated with ortho-hetero substituted aryl bromides and sterically hindered ortho-dimethoxy or rigid ortho-diaryl aryl bromides, showing excellent gamma-site selectivity. The method enables the facile synthesis of CBD-like compounds with selective anti-proliferative effects against glioma stem cells.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Adrian Tlahuext-Aca, Sarah Yunmi Lee, Shu Sakamoto, John F. Hartwig
Summary: A new method for the direct catalytic arylation of simple arenes using aryl bromides is described. The method does not rely on directing groups and instead utilizes a synergistic catalytic cycle involving phosphine-ligated silver complexes and palladium catalysts. Mechanistic experiments indicate that cleavage of the C-H bond by silver is the rate-determining step in the catalytic cycle.
Article
Chemistry, Applied
Haoqiang Zhao, Jianbin Xu, Xin Xu, Yixiao Pan, Zexin Yu, Lijin Xu, Qinghua Fan, Patrick J. Walsh
Summary: The method employs inexpensive, readily available, and safe aryl carboxylic acids with a pyridine directing group to achieve C6-selective C-H arylation, allowing for a wide range of substituted 2-pyridones and affording products in yields of 41-91%.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Asim Kumar Swain, Kubandiran Kolanji, T. Christoph Stapper, Prince Ravat
Summary: This paper describes the stereospecific synthesis and functional properties of C-2- and C-1-symmetric pyrene-fused [5]helicene molecules connected via hexagonal and heptagonal rings. The molecules exhibited high configurational stability and unique functional properties due to the fusing mode of [5]helicene with pyrene and molecular symmetry. The estimated Gibbs activation energy for enantiomerization of one of the molecules was among the highest reported values for any p-conjugated molecules incorporating [5]helicene moiety.
Article
Chemistry, Organic
Zhenhua Li, Lijun Chen, Dayou Rong, Longfeng Yuan, Yuanyuan Xie
Summary: We describe a metal-free photochemical C-H direct arylation using acridone as a photoredox catalyst. Diazonium salts as precursors for aryl radicals enable the functionalization of (hetero)arenes under mild conditions, as demonstrated by a fluorescence quenching experiment and free radical trapping experiment. Valuable substituted biaryl and aryl-heteroaryl compounds were prepared in moderate to good yields via the coupling, and the method is suitable for scale-up synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Dan Wang, Han-Ying Peng, Meng-Meng Yang, Er-jun Hao, Yue-Sheng Li, Zhi-Bing Dong
Summary: A metal-free Cs2CO3-promoted hydrothiolation of alkynes with aryl thioureas for the stereoselective synthesis of (Z)vinyl sulfides has been reported. Vinyl thioethers were obtained with good yields via anti-Markovnikov and cis addition, showcasing potential synthetic value for a diversity of (Z)-vinyl thioethers. This protocol features a broad substrate scope of starting materials, high atom economy, good yields, and exclusive stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Bajin Chen, Shengpeng Wang, Jinxing Song, Xiaojun Wang, Bencheng Yu, Xiaobo Yang
Summary: A novel method has been developed for the direct C-H arylation of quinoxalinones with aryl acylperoxides, which proceeds smoothly through a radical process under catalyst-free condition to give the target products in moderate good yields. This strategy provides a simple and green alternative for synthesizing 3-arylquinoxalinones.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Medicinal
Kuan-Chieh Ching, Thi Ngoc Quy Tran, Siti Naqiah Amrun, Yiu-Wing Kam, Lisa F. P. Ng, Christina L. L. Chai
JOURNAL OF MEDICINAL CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Qinghua Lyu, Hongyan Song, Nikolai L. Yakovlev, Wui Siew Tan, Christina L. L. Chai
Article
Cell & Tissue Engineering
Qixing Zhong, Filip Laco, Mei-Chih Liao, Tsung L. Woo, Steve K. W. Oh, Christina L. L. Chai
STEM CELLS TRANSLATIONAL MEDICINE
(2018)
Article
Chemistry, Analytical
Cheng Li, Mun Hong Ngai, Karnati Konda Reddy, Sandric Chee Yew Leong, Yen Wah Tong, Christina Li Lin Chai
ANALYTICA CHIMICA ACTA
(2019)
Article
Chemistry, Multidisciplinary
Qinghua Lyu, Nathanael Hsueh, Christina L. L. Chai
Review
Materials Science, Biomaterials
Qnghua Lyu, Nathanael Hsueh, Christina L. L. Chai
ACS BIOMATERIALS SCIENCE & ENGINEERING
(2019)
Article
Chemistry, Medicinal
Quy T. N. Tran, W. S. Fred Wong, Christina L. L. Chai
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2019)
Article
Chemistry, Organic
Aymeric Cervi, Yen Vo, Christina L. L. Chai, Martin G. Banwell, Ping Lan, Anthony C. Willis
Summary: Efficient methods for the synthesis of phenol-derived propiolates and their Au(I)-catalyzed cyclization to give coumarins have been reported. These methods have been successfully applied to the synthesis of natural products such as ayapin and scoparone.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Nathanael Hsueh, Christina L. L. Chai
Summary: This study focused on the design and synthesis of catechol-derived ATRP initiators containing the 2-bromoisobutyryl moiety, and investigated the impact of structural changes on initiator immobilization and subsequent ATRP performance. The results showed that changes in the length of the linker unit bearing the 2-bromoisobutyryl moiety, the introduction of a free amine group, or the replacement of the amide with an ester had profound effects on the ability of the molecule to deposit ATRP-initiator-modified PDA coatings, as well as the subsequent SI-ATRP performance.
Review
Chemistry, Medicinal
Malcolm Z. Y. Choo, Christina L. L. Chai
Summary: Many concepts and guidelines in medicinal chemistry can aid in successful drug discovery and development, but rigid and blind use of them may hinder productivity. Therefore, attention should be given to limitations in assays to increase the chances of successful drug discovery.
Article
Chemistry, Medicinal
Quy Thi Ngoc Tran, Regina Ching Hua Lee, Hon Jin Liu, Danli Ran, Vincent Zhan Lin Low, Dong Quang To, Justin Jang Hann Chu, Christina Li Lin Chai
Summary: This study reports a new class of small-molecule CHIKV inhibitors, oxindole-labdanes, which can effectively block the replication of CHIKV with good selectivity. Compound (E)-42 shows high antiviral activity and minimal cytotoxicity to host cells, demonstrating both prophylactic and therapeutic effects. This finding opens up a new avenue for the development of antiviral drugs against CHIKV infection.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Pharmacology & Pharmacy
Wupeng Liao, Hazel Yu Ci Foo, Thi Ngoc Quy Tran, Christina Li Lin Chai, Wai Shiu Fred Wong
Summary: This study evaluated the protective effects of CalD in a house dust mite (HDM)-induced asthma mouse model. CalD reduced various inflammatory markers and improved lung function in the mice. It modulated the function of alveolar macrophages and had potential as a novel anti-inflammatory compound for allergic asthma.
BRITISH JOURNAL OF PHARMACOLOGY
(2023)
Review
Biochemistry & Molecular Biology
Quy T. N. Tran, W. S. Daniel Tan, W. S. Fred Wong, Christina L. L. Chai
Summary: Andrographolide, a widely studied plant secondary metabolite, has diverse pharmacological targets associated with prevalent diseases. Despite documented efficacy in disease models, challenges such as multi-targeting properties and discrepancies in bioavailability have hindered its development as a therapeutic agent.
NATURAL PRODUCT REPORTS
(2021)
Article
Polymer Science
Qinghua Lyu, Nathanael Hsueh, Christina L. L. Chai
Article
Chemistry, Multidisciplinary
Jean-Baptiste Vendeville, Rebecca F. Matters, Anqi Chen, Mark E. Light, Graham J. Tizzard, Christina L. L. Chai, David C. Harrowven
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
