Article
Chemistry, Organic
Zhi-Yong Zeng, Jin-Xi Liao, Zhen-Ni Hu, De-Yong Liu, Qing-Ju Zhang, Jian-Song Sun
Summary: A chemical synthesis protocol for quillaic acid was established using easily available protoescigenin as a starting material, featuring scalability and robustness in each step. The devised protocol also demonstrated outstanding flexibility, allowing for convenient access to other scarce and difficult-to-access oleanane-type aglycones by sharing common intermediates with quillaic acid.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
P. Veeraraghavan Ramachandran, Abdulkhaliq A. Alawaed, Henry J. Hamann
Summary: Deoxyhalogenation of aryl aldehydes, ketones, carboxylic acids, and esters has been achieved by using a suitable metal halide Lewis acid as a carbonyl activator and halogen carrier, in combination with borane-ammonia as the reductant. Selectivity is achieved by matching the stability of the carbocation intermediate with the effective acidity of the Lewis acid. Substituents and substitution patterns significantly influence the choice of solvent/Lewis acid combination. Logical combinations of these factors have also been applied for the regioselective conversion of alcohols to alkyl halides.
Article
Chemistry, Organic
Sven C. Richter, Martin Oestreich
Summary: The chemoselective deoxygenation of secondary benzylic alcohols can be achieved through a series of formylation and reduction reactions, forming formates. In this process, the formyl group acts as both an activator and a self-sacrificing protecting group, allowing the reaction to proceed in the presence of other reducible groups.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Hafsa Karroum, Sergey Chenakin, Sergei Alekseev, Viacheslav Iablokov, Yizhi Xiang, Vincent Dubois, Norbert Kruse
Summary: This study presents a one-step-one-pot synthesis of chain-lengthened aliphatic amines and nitriles using potassium-promoted Co/MnOx catalysts, showing that the reaction can be tuned by adjusting the H-2/CO ratio. Additionally, the addition of NH3 strongly favors the formation of chain-lengthened olefins over alkanes.
Article
Chemistry, Organic
Youngran Seo, Jared M. Lowe, Neyen Romano, Michel R. Gagne
Summary: A variety of C-glycosides can be synthesized through a one-step functionalization process by changing the addition order, Lewis acid, and TMS-X, resulting in common C-pyranosides, rare C-furanosides, and virtually unknown anhydro-C-pyranosides. These synthons are obtained through different mechanisms such as direct substitution, isomerization/substitution, or substitution/isomerization.
Article
Chemistry, Organic
John J. Monteith, Sophie A. L. Rousseaux
Summary: A Negishi cross-coupling method has been developed for the synthesis of alpha-aryl ester products using alpha-hydroxy ester derivatives and arylzinc reagents. This reaction is efficient, rapid, and mild, providing a complementary way of accessing desirable products.
Article
Chemistry, Multidisciplinary
Johnny Z. Wang, Holt A. Sakai, David W. C. MacMillan
Summary: In this paper, a convenient catalytic method for the coupling of alcohols with alkenes under mild photocatalytic conditions using N-heterocyclic carbene (NHC)-mediated deoxygenative Giese-type addition is described. This method is applicable to a wide range of alcohol compounds and allows for late-stage diversification reactions, showing significant potential for various applications.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Liang-Chao Zhu, Dong-Li Yang, Yong Shi
Summary: The novel congeners 5 alpha,6-dihydro of veragranines A and B, with unprecedented hexacyclic skeleton and potent analgesic effects, were synthesized in six steps from hecogenin acetate. This method provides a quick access to the hexacyclic skeleton and can be utilized for preparing other D-ring modified congeners.
Article
Chemistry, Organic
Jia-Xin Wang, Wei Ge, Ming-Chen Fu, Yao Fu
Summary: A novel method for efficient synthesis of beta-gem-difluoroalkene esters was disclosed in this study. The method involves photoredox-catalyzed allylic defluorinative alkoxycarbonylation of trifluoromethyl alkenes through intermolecular alkoxycarbonyl radical addition, and demonstrates wide reaction adaptability and excellent functional group tolerance. Furthermore, successful late-stage modification of bioactive molecules highlights the synthetic value of this method in medicinal research.
Article
Chemistry, Organic
Yutaka Nishiyama, Shijie Xu, Yuuki Hanatani, Susumu Tsuda, Rui Umeda
Summary: The rhenium complex catalyzes the efficient reduction of benzylic, tertiary, and allylic alcohols using hydrosilane, resulting in the formation of alkanes. Different types of alcohols exhibit different side reactions.
TETRAHEDRON LETTERS
(2022)
Review
Chemistry, Physical
Yingdong Zhou, Javier Remon, Zhicheng Jiang, Avtar S. Matharu, Changwei Hu
Summary: The chemical transformation of natural oils provides alternatives to limited fossil fuels and produces compounds with added value for the chemical industries. This review summarizes recent progress in catalytic deoxygenation of natural oils to renewable liquid fuels and valuable fatty alcohols. It also discusses strategies to control product selectivity and proposes future research goals. Rating: 8/10
GREEN ENERGY & ENVIRONMENT
(2023)
Article
Chemistry, Inorganic & Nuclear
Vadim Adamovich, Llorenc Benavent, Pierre-Luc T. Boudreault, Miguel A. . Esteruelas, Ana M. Lopez, Enrique Onate, Jui-Yi Tsai
Summary: The organic molecule H3L was used to synthesize the Ir(III) derivative Ir(kappa 6-fac-C,C ',C ''-fac-N,N ',N ''-L). This compound was formed through coordination and CH bond activation. Reactions were carried out using different starting materials, and different solvents affected the coordination of H3L. The resulting Ir(kappa 6-fac-C,C ',C ''-fac-N,N ',N ''-L) complex showed phosphorescent emission and was utilized in the fabrication of yellow emitting devices with specific properties.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Neha Antil, Ajay Kumar, Naved Akhtar, Rajashree Newar, Wahida Begum, Kuntal Manna
Summary: A heterogeneous catalyst based on aluminum metal-organic framework and cobalt(II) hydride was reported for selective and efficient deoxygenation of a wide range of carbonyls and alcohols. The catalyst can be recycled and operates under ambient hydrogen pressure.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Toolika Agrawal, Robert T. Martin, Stephen Collins, Zachary Wilhelm, Mytia D. Edwards, Osvaldo Gutierrez, Joshua D. Sieber
Summary: A cost-effective and readily available Cu-catalyzed system for reductive coupling of chiral allenamide with N-alkyl substituted aldimines to access chiral 1,2-diamino synthons has been disclosed in this study, providing high yields of single stereoisomers. The method shows broad reaction scope, high diastereoselectivity, and easy scalability. Mechanistic investigations have identified the reversible addition to the imine, impacting the development of catalyst-controlled stereoselective variants of the reductive coupling.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jiayi Liu, Xiao Li, Xinhao Chen, Tao Wang, Liantao Xin, Weisi Guo
Summary: A direct electrochemical reductive approach for deoxygenation of alcohols has been developed using a substoichiometric amount of AlCl3. The released Al ions from the sacrificial Al anode can combine with chloride anions to regenerate the Lewis acid.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Yijie Hu, Xiaoli Wang, Nan Ren, Na Li, Jianyang Li, Jie Chen, Hui Zhang, Hongmei Deng, Weiguo Cao, Jin-Hong Lin
Summary: This study presents the first synthesis of fluoroalkylated benzimidazole- or indole-fused benzoxazines using fluoroalkylated propiolates as building blocks. The reactions proceeded smoothly under mild conditions, giving the desired products in moderate to high yields.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Fang Xiao, Jin-Hong Lin, Fei Hao, Xing Zheng, Yu Guo, Ji-Chang Xiao
Summary: A protocol for visible light mediated C-H trifluoromethylation of unactivated (hetero)arenes under blue LED irradiation has been developed. It enables the rapid construction of a range of CF3-containing (hetero)arenes in moderate to high yields from the readily accessible trifluoromethylsulfonyl-pyridinium salt (TFSP). This protocol is also suitable for nitrogen-containing aromatic heterocycles, which are potentially useful in medicinal chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Bai-Yu Qian, Wei Zhang, Jin-Hong Lin, Weiguo Cao, Ji-Chang Xiao
Summary: In this paper, a convenient anti-Markovnikov iodofluorination of alkenes was described using Selectfluor/(Bu4NI)-Bu-n as the reagent. The reaction showed a broad substrate scope, good functional group tolerance, and the ability to construct various C-F bonds.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Wei Zhang, Xiaoyun Deng, Feng-Xu Zhang, Jin-Hong Lin, Ji-Chang Xiao, Steven H. Liang
Summary: This study discovered the unusual reactivity of the SO2OCF2H group and successfully developed a synthetic tool for well-functionalized alkenyl sulfonyl fluorides, as well as achieving the first 18F labeling of alkenyl sulfonyl fluorides.
Article
Chemistry, Organic
Feng-Xu Zhang, Jin-Hong Lin, Ji-Chang Xiao
Summary: Here, we report the design and synthesis of a difluoromethylsulfonyl imidazolium salt, which serves as a radical difluoromethylation reagent for achieving amino- and oxy-difluoromethylation of alkenes. Importantly, the synthesis of the imidazolium salt can be accomplished without the need for distillation or column chromatography purification, and the amino- and oxy-difluoromethylation pathways are determined by the choice of reaction solvents.
Article
Chemistry, Organic
Yi-Jun Xiang, Shun Liu, Jing Zhou, Jin-Hong Lin, Xu Yao, Ji-Chang Xiao
Summary: Described here is a dehydroxylative sulfonylation method using R3P/ICH2CH2I as a promoter to convert alcohols into sulfonyl compounds. Unlike previous methods that are limited to active alcohols, our protocol can be applied to both active and inactive alcohols (alkyl alcohols). Various sulfonyl groups, including CF3SO2 and HCF2SO2, can be incorporated, which are of interest in pharmaceutical chemistry. The reaction is completed within 15 minutes, and the reagents used are cheap and readily available.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ling-Ying Chen, Peng-Fei Pan, Jin-Hong Lin, Chuan-Ming Jin, Ji-Chang Xiao
Summary: This paper describes a convenient synthesis of an efficient trifluoromethoxylation reagent, C4F9SO3CF3, using cheap and widely available reagents, and without the need for any tedious column chromatography purification procedure.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Wen-Jie Pan, Jiao Yu, Wei-Guo Cao, Ji-Chang Xiao, Jin-Hong Lin
Summary: Difluorocarbene has been used as a versatile intermediate for incorporating fluorinated groups into organic molecules. In this study, it was revealed that difluorocarbene can function as a C-F source for the synthesis of fluorinated benzothiazoles, which may have potential applications in drug development.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Wei-Ying Tang, Xing Zheng, Xu Yao, Jin-Hong Lin, Qu-Tong Zheng, Ji-Chang Xiao
Summary: Due to the widespread occurrence of hydroxyl groups, the reductive deoxygenation of alcohols is an active research area. This study presents a new efficient method using Ph3P/ICH2CH2I and NaBH4, which has a wide substrate scope, good functional group tolerance, and convenient operation with low reagent cost.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
