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)
Review
Chemistry, Multidisciplinary
Li-Jie Cheng, Neal P. Mankad
Summary: Transition metal-catalyzed carbonylation reactions are an effective method to introduce oxygen functionality into organic compounds. However, challenges such as the use of noble metals as catalysts and the reactivity of certain substrates remain.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Organic
Fengxiang Zhu, Pengpeng Yin, Pengbo Zhang
Summary: A convenient four-component reaction has been developed to directly transform aryl iodides with alkyl halides into aromatic esters and diesters via palladium-catalyzed carbonylation with water as solvent. The method exhibits moderate to good yields and broad functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jing-Ao Ren, Jin-He Na, Chao Gui, Chengping Miao, Xue-Qiang Chu, Mengtao Ma, Hao Xu, Xiaocong Zhou, Zhi-Liang Shen
Summary: A nickel-catalyzed direct cross-coupling between unactivated aryl fluorides and aryl bromides was achieved. This one-pot reaction proceeds effectively at room temperature in THF, avoiding the use of preformed and sensitive organometallic reagents. The desired biaryls are produced in modest to good yields via C-F bond cleavage in the presence of a phosphine ligand and magnesium powder (with or without TMSCl).
Article
Chemistry, Organic
Atul Kumar, Gulenur N. Khatun, Rodney A. Fernandes
Summary: An efficient, mild, and economical approach for the regioselective synthesis of 4-aryl/alkyl-1-peroxy-but-3-en-2-ols from 1-substituted-1,3-butadienes using hydroperoxides and catalyzed by TBAI has been achieved. This method is simple to operate, does not require dry conditions, and has excellent tolerance to a wide range of substrates, resulting in good yields of corresponding hydroxyperoxidates. Thus, an outstanding regioselective orthogonal dioxygenation in a diene system has been accomplished.
Article
Chemistry, Organic
Yinpeng Wang, Mingming Zhao, Jingke Peng, Hongxia Zheng, Heng-Ying Xiong, Guangwu Zhang
Summary: The first Pd(0)-catalyzed synthesis of aryl-methylene ethers from hydrobenzoxazoles (hydrothiazoles) using dichloromethane (DCM) as the C1 feedstock is reported. This protocol demonstrates a broad substrate scope (38 examples) and wide tolerance to functional groups. The aryl-methylene ether adducts have been successfully coupled with isocyanate to provide bis-iminoisoindolinones. In this reaction, DCM serves as a twofold electrophile, undergoing double C-Cl bond cleavage to react with hydrobenzoxazoles.
Article
Chemistry, Organic
Xing-Wei Gu, Xiao-Feng Wu
Summary: Transition metal-catalyzed carbonylation of alkyl halides is an efficient method for synthesizing aliphatic carbonyl-containing compounds. This paper discusses recent developments in the carbonylation reactions of alkyl bromides and chlorides catalyzed by abundant metals.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Jin-He Na, Xiang Liu, Jia-Wen Jing, Jing Wang, Xue-Qiang Chu, Mengtao Ma, Hao Xu, Xiaocong Zhou, Zhi-Liang Shen
Summary: A step-economical and efficient one-pot reaction was developed for the direct cross-coupling of aryl fluorosulfate with aryl bromide. This reaction, conducted at room temperature in THF solvent, does not require the use of preprepared/commercial organometallic reagents. By utilizing nickel catalyst, magnesium turnings, and lithium chloride, the desired biaryls were obtained in moderate to good yields with reasonable functional group compatibility.
Article
Chemistry, Organic
Jadab Majhi, Bohang Zhou, Yuxin Zhuang, Mai-Jan Tom, Huifang Dai, P. Andrew Evans
Summary: The palladium-catalyzed cross-coupling reaction provides a convenient and versatile approach for the synthesis of biaryl ketones. This method represents the first application of arylation of cyanohydrins, where cyanohydrins serve as acyl anion equivalents. In contrast to classical cross-coupling reactions, this method allows further functionalization and has significant synthetic utility.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Xi Sun, Xu Dong, Yi Yang, Jiangchen Fu, Yan Wang, Zirui Li, Yuying Liu, Hui Liu
Summary: A novel and convenient palladium-catalyzed cascade reaction has been developed for the synthesis of potentially bioactive hexahydroindole derivatives, demonstrating high functional group tolerance and stereoselectivity. Mechanistic studies suggest the involvement of an alkyl radical pathway in this reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Guifang Chen, Bo Xu
Summary: We have developed a C-O cross-coupling reaction between (hetero)aryliodides and silver carboxylates using a Au-I/Au-III catalytic cycle. This transformation shows exclusive chemoselectivity and is insensitive to moisture and air. It is applicable to both aromatic and aliphatic (including primary, secondary, and tertiary) silver carboxylates, and works well in both intermolecular and intramolecular settings. Importantly, high yields are obtained regardless of the electronic effect and steric hindrance of the substrates.
Article
Chemistry, Organic
Tingzhi Lin, Pengcheng Qian, Yan-En Wang, Mingjie Ou, Ning Cui, Yu Ye, Rui Hua, Dan Xiong, Fei Xue, Patrick J. Walsh, Jianyou Mao
Summary: A direct and convenient method for the synthesis of aryl/alkenyl alkyl ketones has been developed. This method overcomes the limitations of previous methods and avoids the use of organometallic reagents.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Regina M. Oechsner, J. Philipp Wagner, Ivana Fleischer
Summary: We present a catalytic system that allows for mild and fast coupling of aryl chlorides with primary, secondary, and previously challenging tertiary alkyl thiols using an air-stable nickel(II) precatayst in combination with cost-effective potassium acetate as a base at room temperature. This system exhibits excellent tolerance towards various functional groups and yields thioethers in high yields, including pharmaceutical compounds. The chemoselective functionalization of disubstituted substrates is successfully demonstrated.
Article
Chemistry, Organic
Ning Cui, Tingzhi Lin, Yan-En Wang, Jian Wu, Yuheng Han, Xinyang Xu, Fei Xue, Dan Xiong, Patrick J. Walsh, Jianyou Mao
Summary: A nickel-catalyzed reductive cross-coupling reaction has been developed for the synthesis of aryl alkyl ketones from aryl cyclopropyl ketones and unactivated alkyl bromides. The reaction proceeds via radical cleavage of the alkyl bromide, and provides access to a variety of gamma-alkyl-substituted ketones through ring opening of cyclopropyl ketones (26 examples, 50-90% yield).
Article
Chemistry, Organic
Hao Xu, Cai-Yu He, Bo-Jie Huo, Jia-Wen Jing, Chengping Miao, Weidong Rao, Xue-Qiang Chu, Xiaocong Zhou, Zhi-Liang Shen
Summary: In this study, a cross-electrophile coupling of aryl thiols with aryl bromides was reported, where C-S bond activation occurred instead of S-H bond cleavage, leading to the formation of thioethers as the major products. The reaction proceeded effectively with a nickel catalyst, magnesium turnings, and lithium chloride in THF at room temperature, and a variety of structurally diverse biaryls were obtained in moderate to good yields.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Jia-Hao Chen, Wasim Ahmed, Ming-Hua Li, Zhao-Dong Li, Zi-Ning Cui, Ri-Yuan Tang
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Organic
Zhu Zhu, Jinggong Liu, Shoucheng Dong, Bolai Chen, Zhenghui Wang, Ri-yuan Tang, Zhaodong Li
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Yong-Chao Gao, Zi-Hao Huang, Zhao-Sheng Zhang, Jin-Xin Xie, Zi-Ning Cui, Ri-Yuan Tang
SYNTHESIS-STUTTGART
(2020)
Article
Chemistry, Organic
Zhuoxian Shao, Shaoyi Zhang, Yihan Chen, Yun-Lin Liu, Ri-Yuan Tang, Zhaodong Li
Article
Chemistry, Organic
Zhuo-Bin Huang, Xue-Ying Guo, Zi-Hao Huang, Ming-Hua Li, Shou-Cheng Dong, Ri-Yuan Tang
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Jian-Xiong He, Huan-Yu Pan, Li Xu, Ri-Yuan Tang
Summary: Aflatoxins are highly toxic carcinogens, and molecular imprinting polymers have been widely applied for their detection and separation. Different polymerization methods and applications of molecular imprinting polymers in aflatoxin detection were reviewed in this study.
JOURNAL OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Wasim Ahmed, Zi-Hao Huang, Zi-Ning Cui, Ri-Yuan Tang
Summary: This study reports the synthesis of unique mesoionic thiazoloisoquinolinium thiolates via cycloaddition reaction, which shows good bioactivity against the chlorophyll of duckweed.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Yiming Du, Shuxin Chen, Ao Huang, Yihan Chen, Yun-Lin Liu, Gaopeng Song, Ri-Yuan Tang, Hanhong Xu, Guangkai Yao, Zhaodong Li
Summary: This article reports a versatile and expeditious method for site-selective C-H fluoromethylation of aryl iodides via Pd/norbornene cooperative catalysis. It can serve as a robust toolbox for the diversity-oriented synthesis (DOS) of fluoromethylated arenes. The method features the use of low-cost industrial raw material CH2IF as the fluoromethyl source, excellent functional group tolerance, and broad ipso termination scope. It can also be applied to the late-stage modification of biorelevant molecules.
Article
Chemistry, Multidisciplinary
Shuxin Chen, Xue Liu, Kaidian Li, Wenchao Yang, Jian Lin, Ri-Yuan Tang, Hanhong Xu, Zhaodong Li
Summary: A novel approach based on Pd/norbornene cooperative catalysis is presented for the efficient assembly of beta-fluoroalkylated arenes. The method shows excellent functional group tolerance and a wide range of ipso termination reactions. Additionally, it enables the synthesis of diverse fluorinated macrolactones under mild reaction conditions, which is otherwise extremely challenging.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Medicinal
Jinxin Xie, Lijuan Wang, Xiaoyong Zhang, Yiyang Li, Xin Liao, Caixin Yang, Ri-Yuan Tang
Summary: Aryloxyethyl propiolates and their homologues are promising anti-MRSA agents with multiple targets, as they can destroy the cell wall and cell membrane, inhibit the formation of a biofilm, and bind to the DNA of MRSA.
ACS INFECTIOUS DISEASES
(2022)
Article
Chemistry, Applied
Guangkai Yao, Chuanle Zhu, Tianyi Qin, Mengfan Wang, Zhixiu Sun, Ri-Yuan Tang, Chen Zhao, Huanfeng Jiang, Hanhong Xu
Summary: The oxidative [3+2+1] annulation reaction of aldehydes, 5-aminopyrazoles, and nitriles under the oxidation of I-2/O-2 produces valuable pyrazolo[3,4-d]pyrimidines in yields of 27%-91%. This reaction is notable for being transition-metal free, operationally simple, having a broad substrate scope, good functional group tolerance, and being scalable.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Agriculture, Multidisciplinary
Zi-Hao Huang, Xue-Ying Guo, Lan-Tu Xiong, Li Dong, Jin-Tong Jian, Lin-Hao Wei, Ri-Yuan Tang, Han-Hong Xu
Summary: In this study, novel N-difluoromethyl triazole selenoureas have been developed as a versatile artificial organoselenides defense (AOSeD) for controlling pests, phytopathogenic fungi, and weeds. Furthermore, the AOSeD is safe for tomato plants and Brassica campestris.
ACS AGRICULTURAL SCIENCE & TECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Jinxin Xie, Benjian Liao, Hui Zhu, Yongfei Yu, Ri-Yuan Tang
Summary: The study synthesized novel 2-methyl-3-furyl sulfide flavor derivatives and evaluated their antimicrobial activity against foodborne bacteria and fungi. Fifteen compounds were found to have potential as preservatives for food production, with some showing better antimicrobial activity than traditional control groups.
Review
Agriculture, Multidisciplinary
Jinxin Xie, Benjian Liao, Ri-Yuan Tang
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2020)
Article
Chemistry, Organic
Zhuo-Bin Huang, Xiong-Jian Xia, Zi-Hao Huang, Li Xu, Xiao-Yong Zhang, Ri-Yuan Tang
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
