Article
Chemistry, Organic
Hongbin Zhai, Dong Liu, Taimin Wang
Summary: A nine-step asymmetric total synthesis of (+)-tubingensin A has been achieved, featuring intramolecular Heck reaction for establishing the key vicinal quaternary stereocenter motif present in the natural product and late-stage Zweifel olefination for side chain elongation.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Hongbin Zhai, Zhenhua Wang, Kewei Chen, Tian-Yu Sun, Jian Wei, Yun-Dong Wu
Summary: The first asymmetric total synthesis of indole alkaloid arbophyllidine has been achieved, featuring key reactions such as intramolecular reductive Heck reaction, Fischer indolization, and oxidative lactonization. Density functional theory calculations were employed to provide a comprehensive understanding of the oxidative lactonization.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Ling Yang, Dong-Hang Tan, Wen-Xin Fan, Xu-Ge Liu, Jia-Qiang Wu, Zhi-Shu Huang, Qingjiang Li, Honggen Wang
Summary: A new method was proposed utilizing benzyl N-methyliminodiacetyl (MIDA) boronates for photochemical radical C-H halogenation, enabling successful fluorination, chlorination, and bromination reactions. The resulting brominated product could be further transformed into a variety of organic compounds, including those difficult to form with alpha-halo sp(2)-B boronate esters, by reaction with different nucleophiles. An activation effect of the B(MIDA) moiety was discovered.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Cong-Cong Lu, Bo-Ya Hao, Ya-Ping Han, Yong-Min Liang
Summary: This article reviews the recent advances in the dearomative annulation of N-acylindoles with diverse nucleophiles since 2012, which can be classified into five categories: Dearomative Heck reactions, visible-light-induced reductive dearomatization, Lewis acid-catalyzed dearomative reductive reactions, asymmetric dearomative Heck reactions, and dearomative Heck reactions with other closely related N-acylindole reagents.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Chao-Ting Yen, Yi-Hung Liu, Shie-Ming Peng, Shiuh-Tzung Liu
Summary: A palladium-promoted Mizoroki-Heck type reaction using a directing-group strategy efficiently produces coupled vinyl cyclopentenes with excellent regio- and stereoselectivity. Interestingly, it was found that the stereochemistry of the vinylic substrates is inverted in the products.
Article
Chemistry, Multidisciplinary
Xianfeng Li, Juan Zhang, Changyang Liu, Jie Sun, Yangfeng Li, Gong Zhang, Yizhou Li
Summary: This article reports on a palladium-catalyzed cross-coupling technique using DNA-conjugated aryl diazonium intermediates for DNA-encoded chemical library synthesis. The method allows for the synthesis of diverse chemical compounds with broad substrate scope and excellent functional group tolerance under mild conditions. It also enables the construction of DNA-tethered pharmaceutical compounds without compromising their bioactivity. This approach demonstrates its potential for creating medicinally relevant combinatorial libraries and investigating protein-ligand interactions in pharmaceutical research.
Article
Chemistry, Applied
Ze-Jian Xue, Meng-Yao Li, Bin-Bin Zhu, Zhi-Tao He, Chen-Guo Feng, Guo-Qiang Lin
Summary: The palladium-catalyzed cross-coupling of ortho-vinyl aromatic bromides and olefins using a controllable 1,4-palladium migration/Heck cascade protocol is a mild, efficient, and highly stereoselective method for the synthesis of trisubstituted 1,3-dienes, especially triaryl-substituted ones.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Maxwell B. Haughey, Kirsten E. Christensen, Darren L. Poole, Timothy J. Donohoe
Summary: The successful synthesis of the complex taiwanschirin fused [8,6,5] core, representing challenging and biologically active targets, was achieved through a novel alkynylation reaction and intramolecular Heck reaction method.
Article
Chemistry, Applied
Fabio Wilbert, Thomas J. J. Muller
Summary: One-pot syntheses of 3,3-diarylallylidene indolinones were achieved by pseudo-four-and pseudo-five-component reactions. The title compounds, which are a mixture of E/Z-configured isomers, were assessed for their photophysical characteristics using absorption and solid-state emission spectroscopy. The fluorescence of 3,3-diarylallylidene indolinones in the solid state was observed regardless of their configuration, but only when electron-withdrawing and weakly electron-releasing remote p-phenyl substituted dyes were present with concomitant Boc substitution of the lactam moiety. DFT and TD-DFT calculations were used to reproduce and rationalize the electronic structure of the longest wavelength absorption and emission bands.
Article
Chemistry, Multidisciplinary
Bowen Li, Bangke Luo, He Yang, Wenjun Tang
Summary: This study reports an efficient palladium-catalyzed Heck reaction for the synthesis of heterocycles with α-heteroaryl substitution. The method exhibits a broad substrate scope and excellent functional group compatibility. The use of a sterically bulky ligand containing an anthryl moiety is crucial for this transformation. Additionally, an asymmetric variant of the Heck reaction has been achieved, enabling the efficient asymmetric synthesis of (S)-nicotine and its analogues via a cationic palladium pathway.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Gokanapalli Anusha, Meeniga Indira, Shaik Farheen Banu, Peddiahgari Vasu Govardhana Reddy
Summary: A series of Pd-N-heterocyclic carbenes complexes were synthesized and used as catalysts for C2-arylation, C-C, and C-heteroatom bond formation reactions. In this study, we focused on synthesizing styryl pyridines via Heck coupling reactions and oxidative Heck coupling reactions. Two methods were utilized: method i involved terminal alkenes and aryl halides, while method ii involved aryl boronic acids, terminal alkenes, oxidant, and Pd-PEPPSI catalyst. The results showed that the boronic acids gave higher yields compared to aryl halides, and the catalyst could be reused without loss of activity. The prepared styryl pyridine derivatives exhibited E-configuration and their photophysical properties were characterized by absorption and emission spectra.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Shen Tan, Yu-Tao He, Ping Lan, Martin G. Banwell, Lorenzo V. White
Summary: A seven-step total synthesis of (-)-thebaine from simple, commercially available starting materials is reported. Key steps include successive coupling and substitution reactions, as well as a photochemical hydroamination reaction.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Xiaolei Huang, Shenghan Teng, Yonggui Robin Chi, Wenqiang Xu, Maoping Pu, Yun-Dong Wu, Jianrong Steve Zhou
Summary: The nickel-catalyzed intermolecular Heck reaction of cycloalkenes with aryl triflates, mesylates, and tosylates shows excellent enantiomeric ratios. Additionally, the asymmetric reductive Heck reaction is also applicable to a 2-cyclopentenone ketal, equivalent to conjugate arylation of the enone itself.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Taiki Mori, Koki Abe, Seiji Shirakawa
Summary: An efficient enantioselective synthesis of important pharmaceutical building blocks called gamma-chiral alpha-spiro-gamma-lactones was achieved through a catalytic bromo-lactonization reaction using BINOL-derived chiral bifunctional sulfide. This reaction is suitable for alpha-allyl carboxylic acids containing different structures. The resulting alpha-spiro-type bromolactonization product can be transformed to obtain optically active gamma-functionalized alpha-spiro-gamma-lactones. This catalytic system was also proven useful in the asymmetric synthesis of alpha,alpha-diaryl- and dialkyl-substituted gamma-lactones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Gennady I. Borodkin
Summary: This review summarizes and critically analyzes the data on the mechanochemical synthesis of halogen-containing organic compounds published mainly over the past 10 years. The established views about the methods of activation of mechanochemical halogenation reactions are discussed. The review considers the mechanochemical fluorination, chlorination, bromination, and iodination reactions of organic compounds. Special attention is given to reaction mechanisms, selectivity problems, and the consideration of mechanochemical approach as a promising trend of green chemistry.
RUSSIAN CHEMICAL REVIEWS
(2023)
Article
Biochemistry & Molecular Biology
Jie Cheng, Zhenlong Gu, Caiyu He, Jie Jin, Lijun Wang, Guojun Li, Bei Sun, Hui Wang, Jun Bai
CARBOHYDRATE RESEARCH
(2015)
Article
Chemistry, Multidisciplinary
Jun Zhang, Meng Zhao, Wenjie Xie, Jie Jin, Fazhi Xie, Xiaojie Song, Shengyi Zhang, Jieying Wu, Yupeng Tian
NEW JOURNAL OF CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Shibiao Wu, Ling Xu, Haiyan Xu, Feifei Li, Jie Jin, Qiushi Yao, Yuan Wang, Dekai Hong
ASIAN JOURNAL OF CHEMISTRY
(2013)
Article
Chemistry, Organic
Jie Jin, Ling Dong, Kehua Zhang, Jin Liu
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Medicinal
Jie Jin, Peng Teng, Hai-Liang Liu, Jing Wu, Yu-Mei Liu, Qiang Xu, Jian-Xin Li
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2013)
Article
Obstetrics & Gynecology
Yu Zhao, Yue Huai, Jie Jin, Mei Geng, Jian-Xin Li
MENOPAUSE-THE JOURNAL OF THE NORTH AMERICAN MENOPAUSE SOCIETY
(2011)
Article
Chemistry, Organic
Zhang-Shuang Deng, Yu Zhao, Cui-Cui He, Jie Jin, Yun-Mian He, Jian-Xin Li
Article
Chemistry, Organic
Jie Jin, Min-Min Cai, Jian-Xin Li
Article
Chemistry, Multidisciplinary
Tong Lu, Ling Dong, Hongmei Pan, Xuedan Wu, Xia Chen, Chengwen Gu, Naili Tao, Ao Wang, Kehua Zhang, Jie Jin
JOURNAL OF CHEMICAL RESEARCH
(2020)
Article
Chemistry, Inorganic & Nuclear
Jie Jin, Shanshan Wu, Jing Wang, Yunqi Xu, Shouhu Xuan, Qunling Fang
Summary: A MXene@AgPd/PDA nanosheet with excellent photothermal conversion efficiency was synthesized. The nanosheet had a cage-like nanostructure with AgPd bimetallic nanocrystals sandwiched between a MXene nanosheet and PDA layer. The nanosheet exhibited good catalytic activity for the reduction of 4-nitrophenol and improved catalytic dynamics under NIR irradiation. It also showed good antibacterial activity, which was further enhanced under NIR light due to the photothermal effect.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Organic
Jie Jin, Ruixiang Xu, Xuedan Wu, Xiaolong Fang, Weili Kong, Kehua Zhang, Jie Cheng
Summary: The synthesis of novel sinomenine N-heterocyclic derivatives, including D-ring tetrazole-isoxazole and tetrazole-triazole derivatives, was achieved through 1, 3-dipolar cycloaddition reactions at N-CH3. A total of 34 derivatives were obtained in yields of 69-93%. The N-CH3 of sinomenine was first converted into N-CN, which then reacted with sodium azide to yield the N-tetrazole derivative. Further reactions with isoxazole bromides and prop-argyl bromide resulted in the formation of tetrazole-isoxazole and tetrazole-triazole derivatives, respectively. The synthesized derivatives were characterized using FT-IR, HRMS, 1H NMR, and 13C NMR spectroscopy.
Article
Chemistry, Applied
YJ Shang, J Jin, YG Wang
REACTIVE & FUNCTIONAL POLYMERS
(2006)
Article
Chemistry, Organic
YJ Shang, J Jin
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2005)
Article
Chemistry, Organic
Xinwei He, Jie Jin, Cuie Wang, Yongjia Shang
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2009)
