Article
Chemistry, Multidisciplinary
Yujie Dong, Jun Liu, Xing Gao, Ting Pan, Biming Mao, Songcheng Yu, Yongjun Wu, Cheng Zhang, Hongchao Guo
Summary: A palladium-catalyzed cascade cyclization was developed for the synthesis of biologically active tetracyclic dihydrocyclopentaindenofuranone derivatives. The reaction exhibited moderate to high yields and excellent diastereoselectivities, with the allene moiety fully fused into the cyclopentene ring.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Ken Sakata, Yuuri Uehara, Shiona Kohara, Takeshi Yoshikawa, Yoshiaki Nishibayashi
Summary: In this study, the effects of propargylic substituents on the enantioselectivity and reactivity in propargylic substitution reactions were further investigated using density functional theory calculations. The results showed that substitution of a methyl group at the propargylic position could reverse the stereoselectivity, while substitution of a trifluoromethyl group for a methyl group was suggested to enhance the enantioselectivity.
Article
Chemistry, Multidisciplinary
Binfang Yuan, Senmao Liu, Tian Liu, Qing Li, Yulu Wang, Zhihui Guo, Xiaogang Guo, Huisheng Huang, Rongxing He
Summary: The mechanisms of Cu(ii)/DBU-catalyzed carboxylation of homopropargylic amines with CO2 to construct 6-methylene-1,3-oxazin-2-ones were studied using density functional theory. Cu(ii) catalysts have a positive effect on the intramolecular cyclization process, and their catalytic activities are determined by their coordination abilities ((DBU)CuCl2 < CuCl2 < [(DBU)CuCl](+)). Additionally, this study revealed three roles of DBU in the reaction: proton-acceptor, nucleophilic agent, and ligand. The theoretical study explains the selectivity of Cu(ii)-catalyzed reactions and the formation of 6-membered products.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Huanan Wang, Hui Qian, Junliang Zhang, Shengming Ma
Summary: A new reaction method for the synthesis of axially chiral allenyl phosphonates through palladium-catalyzed carbon-phosphorus bond formation has been developed. The reaction exhibits high yields and enantioselectivity, and can accommodate a wide range of functional groups. Mechanistic studies have revealed an important kinetic resolution process.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Jun Yang, Lina Yang, Jing Gu, Li Shuai, Hui Wang, Qin Ouyang, Yu-Long Li, Haibin Liu, Liang Gong
Summary: In this study, a nickel-catalyzed reductive deaminative arylalkylation of tethered alkenes with pyridinium salts as C(sp(3)) electrophiles is described. This two-component dicarbofunctionalization reaction enables the efficient synthesis of various benzenefused cyclic compounds bearing all-carbon quaternary centers. The method proceeds under mild conditions and tolerates a wide range of functional groups and heterocycles, making it applicable for late-stage functionalization of complex molecules.
Article
Chemistry, Organic
Yetong Zhang, Lepeng Chen, Yinlin Shao, Fangjun Zhang, Zhongyan Chen, Ningning Lv, Jiuxi Chen, Renhao Li
Summary: The study presents a three-component tandem reaction allowing the synthesis of polysubstitution quinolines using 2-aminobenzonitriles, arylboronic acids, and ketones. This method is practical, efficient, and delivers functional quinolines with moderate to good yields and high functional group tolerance. Additionally, a new method for introducing halogen substituents into the target products has been developed, showing potential for further synthetic elaborations.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Wen-Ya Lu, Yong You, Ting-Ting Li, Zhen-Hua Wang, Jian-Qiang Zhao, Wei-Cheng Yuan
Summary: A new method for synthesizing allenyl thioether compounds via CuI-catalyzed decarboxylative thiolation of terminal alkyne-substituted cyclic carbonates/carbamates has been successfully developed. A variety of hydroxymethyl- and aminomethyl-containing allenyl thioethers were obtained in good to excellent yields under mild conditions. The copper-allenylidene intermediate plays a crucial role in the decarboxylative thiolation reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Yong You, Yan-Ping Zhang, Zhen-Hua Wang, Jian-Qiang Zhao, Jun-Qing Yin, Wei-Cheng Yuan
Summary: Copper-catalyzed decarboxylative reactions of propargylic cyclic carbonates/carbamates are an efficient way to construct various useful skeletons. The field has gained attention and made significant progress due to the reaction sites of propargylic cyclic carbonates/carbamates and the advantages of copper catalysis. This review addresses the achievements, mechanisms, synthetic applications, limitations, challenges, and opportunities in this field.
CHEMICAL COMMUNICATIONS
(2023)
Article
Economics
Dao-Qing Dong, Hao Yang, Meng -Yu Zhou, Ze-Hui Wei, Pei Wu, Zu-Li Wang
Summary: As a reaction medium, water can enhance the conversion and selectivity of organic reactions by utilizing its own properties. This review focuses on palladium-catalyzed reactions in water and provides a summary of relevant articles published in the past two years. The review is divided into three parts based on the type of reaction: cyclization reactions, Suzuki coupling reactions, and miscellaneous reactions.
QUARTERLY REVIEW OF ECONOMICS AND FINANCE
(2023)
Article
Chemistry, Multidisciplinary
Dao-Qing Dong, Hao Yang, Meng-Yu Zhou, Ze-Hui Wei, Pei Wu, Zu-Li Wang
Summary: This article discusses the importance of water as a reaction medium and summarizes the recent research in the field of palladium-catalyzed reactions in water, including cyclization reactions, Suzuki coupling reactions, and miscellaneous reactions.
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Bowen Dou, Kang Wang, Jianbo Wang
Summary: In this paper, we report an efficient method for the synthesis of alkynylated furan derivatives using a Pd-catalyzed oxidative cross-coupling reaction between allenyl ketones and terminal alkynes. This novel synthesis demonstrates the generality of carbene-based cross coupling, and offers an operationally simple and wide substrate scope approach to access alkynylated furan derivatives with good functional group tolerance.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Shiyao Liu, Yoshiaki Tanabe, Shogo Kuriyama, Ken Sakata, Yoshiaki Nishibayashi
Summary: In this study, propargylic substitution reactions using ruthenium and copper catalysis with N-monosubstituted hydrazones as ambident nucleophiles were investigated. It was found that N-monosubstituted hydrazones exhibited different reactivities depending on the catalytic system, resulting in either propargylic alkylated or aminated products. DFT calculations were used to study the reaction pathways and further transformation of the products yielded multisubstituted pyrazoles in good to high yields.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Editorial Material
Chemistry, Multidisciplinary
Shiyao Liu, Yoshiaki Tanabe, Shogo Kuriyama, Ken Sakata, Yoshiaki Nishibayashi
Summary: The cover of this issue features the research on the propargylic substitution reaction of propargylic alcohol with an N-monosubstituted hydrazone, where the nucleophilicity of the hydrazone is controlled by the choice of catalytic system. The full article can be accessed at 10.1002/chem.202103287.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Hao-Peng Lv, Xiao-Peng Yang, Bai-Lin Wang, Hao-Di Yang, Xing-Wang Wang, Zheng Wang
Summary: An asymmetric [3 + 2] cycloaddition reaction has been developed for the synthesis of chiral multistereogenic vinyltetrahydrofurans using the Pd complex of a bidentate phosphoramidite (Me-BIPAM) as the catalyst. The reaction provides a wide variety of products in good yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, 99% ee).
Article
Chemistry, Multidisciplinary
Mandapati Bhargava Reddy, Eoghan M. Mcgarrigle
Summary: An unprecedented carboxylative sulfonylation reaction of (homo)propargyl amines with CO2 and sodium arylsulfinates under visible light irradiation has been developed, exhibiting high efficiency. The ruthenium-catalyzed photochemical protocol offers a wide range of substrates, resulting in good yields of 2-oxazolidinones and 2-oxazinones bearing alkyl sulfones under ambient reaction conditions. In situ double bond isomerization occurs in tandem. The mechanism of these radical-initiated carboxylative cyclizations involving sulfinyl radicals is explained based on control and quenching experiments.
CHEMICAL COMMUNICATIONS
(2023)
