Article
Multidisciplinary Sciences
Samer Gnaim, Adriano Bauer, Hai-Jun Zhang, Longrui Chen, Cara Gannett, Christian A. Malapit, David E. Hill, David Vogt, Tianhua Tang, Ryan A. Daley, Wei Hao, Rui Zeng, Mathilde Quertenmont, Wesley D. Beck, Elya Kandahari, Julien C. Vantourout, Pierre-Georges Echeverria, Hector D. Abruna, Donna G. Blackmond, Shelley D. Minteer, Sarah E. Reisman, Matthew S. Sigman, Phil S. Baran
Summary: The study and application of TMHs in energy storage and organic synthesis is of great importance. The electrochemical approach for utilizing TMHs in organic synthesis offers benefits in terms of sustainability, efficiency, chemoselectivity, and reactivity.
Article
Chemistry, Multidisciplinary
Zhunzhun Yu, Yaxian Kong, Baiqing Li, Shimin Su, Jianhang Rao, Yadong Gao, Tianyong Tu, Hongming Chen, Kuangbiao Liao
Summary: Here, we developed a DHP derivative-catalyzed decarboxylative selenation reaction that showed a broad substrate scope, with the assistance of high-throughput experimentation (HTE) and artificial intelligence (AI). The AI-based model could identify the key structural features and give accurate prediction of unseen reactions. Our work not only developed the catalytic applications of DHP derivatives, but also demonstrated the power of the combination of HTE and AI to advance chemical synthesis.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jiufeng Wu, Claire M. Young, Andrew D. Smith
Summary: A new protocol has been developed for the isothiourea-catalysed transfer hydrogenation of alpha,beta-unsaturated para-nitrophenyl esters using Hantzsch ester. Good to excellent yields were observed, especially with alpha,beta-unsaturated aryl esters bearing electron-withdrawing beta-substituents. The aryl ester products can be isolated directly in moderate to excellent yields or converted to methyl esters or benzyl amides after in situ reaction with the appropriate nucleophile. Preliminary experiments showed modest enantioinduction when a chiral isothiourea catalyst was used.
Article
Chemistry, Organic
Gang Liu, Congcong Yin, Xuanliang Yang, Anqi Li, Minyan Wang, Xumu Zhang, Xiu-Qin Dong
Summary: A highly chemo- and enantioselective hydrogenation method for beta-sulfonyl-alpha,beta-unsaturated ketones was successfully developed, producing a variety of enantioenriched gamma-ketosulfones in good to high yields with excellent selectivities. Gram-scale asymmetric hydrogenation was carried out smoothly with high yields and selectivities. Preliminary DFT computations provided a reasonable explanation for the observed high chemoselectivity and enantioselectivity.
Article
Chemistry, Organic
Chaoqiong Wang, Fang Xie, Qianling Guo, Chaochao Xie, Guofu Zi, Weiping Ye, Zhangtao Zhou, Guohua Hou, Zhanbin Zhang
Summary: The first asymmetric hydrogenation of beta,beta-diaryl unsaturated phosphonates has been achieved with excellent enantioselectivities using the Rh-(R, R)-f-spiroPhos complex as catalyst. This method also shows comparable performance for beta-aryl-beta-alkyl unsaturated phosphonates, providing chiral phosphonates with high ee values. This new methodology offers a straightforward approach to asymmetric synthesis of chiral phosphonates.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Guoqi Zhang, Haisu Zeng, Shengping Zheng, Michelle C. Neary, Pavel A. Dub
Summary: The synthesis of branched Markovnikov's alcohols is crucial in the chemical industry. A highly regioselective hydroboration reaction using alkali metal triethylborohydrides as catalysts was discovered. This method allows for the selective and quantitative reduction of asymmetrical epoxides.
Article
Chemistry, Organic
Xiaolan Jiang, Xiaofeng Cui, Jinxun Chen, Qixing Liu, Yongsheng Chen, Haifeng Zhou
Summary: A chemoselective iridium-catalyzed transfer hydrogenation of α,β-unsaturated ketones was achieved in water, resulting in a series of 2-benzyl indanones and analogues with high yields and good functional group tolerance. The practicality of this approach was demonstrated through gram-scale synthesis.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Peter McNeice, Marc-Andre Mueller, Jonathan Medlock, Werner Bonrath, Nils Rockstroh, Stephan Bartling, Henrik Lund, Kathrin Junge, Matthias Beller
Summary: Researchers have achieved the synthesis of vitamin precursors using a lead- and palladium-free catalyst. The catalyst, made of cobalt nanoparticles supported on silica modified by nitrogen doped carbon, allows the production of various fine chemicals and vitamin precursors. It can be conveniently recycled and used multiple times with consistent activity, selectively hydrogenating alkynes in the presence of easily reducible functional groups, making it a versatile catalyst for synthetic organic chemistry.
Article
Chemistry, Multidisciplinary
Tomasz Bereta, Ewa Mieczynska, Sylwia Ronka, Wlodzimierz Tylus, Anna M. Trzeciak
Summary: In the hydrogenation of acetophenone catalyzed by a new Pd/S-DVB catalyst, a solvent effect was found to impact the reaction efficiency. The solvent's hydrogen-bond-acceptance capacity correlates with the conversion of acetophenone, and binary mixtures of alcohol and water significantly decrease the reaction efficiency due to the microheterogeneity and blocking of the catalyst surface.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
On Ying Yuen, Chau Ming So
Summary: This article discusses the recent development of gamma-arylation of alpha,beta-unsaturated carbonyl compounds and presents the ligand-controlled, site-selective alpha- and gamma-arylation of alpha,beta-unsaturated carbonyl ketones with (hetero)aryl halides. The site selectivity of the reaction can be switched by simply changing the phosphine ligand.
Article
Chemistry, Organic
Bram B. C. Peters, Jira Jongcharoenkamol, Suppachai Krajangsri, Pher G. Andersson
Summary: Asymmetric hydrogenation of conjugated enones using chiral bidentate IrN,P complexes allowed for the preparation of ketones with stereogenic centers at both the alpha- and beta-positions, achieving high enantiomeric excesses of up to 99% and good to high isolated yields even with challenging dialkyl substituted substrates.
Article
Chemistry, Organic
Yogesh Sharma, Ganesh P. Pawar, Vinod D. Chaudhari
Summary: This study presents a facile method for the synthesis of BTDO via a water-gas shift reaction. The method is cost-effective and exhibits remarkable chemical tolerance to a wide range of substituents.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yogesh Sharma, Ganesh P. Pawar, Vinod D. Chaudhari
Summary: Benzothiazine 1,1-dioxide (BTDO), a privileged chemical motif, can be synthesized through a cost-effective and environmentally beneficial domino approach using a water-gas shift reaction (WGSR) with sodium 2-nitrobenzenesulfinates and alpha-bromo ketones. The optimized reaction conditions show remarkable chemical tolerance to various electronically and sterically diverse substituents on both coupling partners.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jiaming Liu, Shang Gao, Evangelos Miliordos, Ming Chen
Summary: Cu-catalyzed highly stereoselective and enantiodivergent syntheses of (Z)- or (E)-beta,?-unsaturated ketones from 1,3-butadienyl silanes are developed. The nature of the silyl group of the dienes has a significant impact on the stereo- and enantioselectivity of the reactions. The reactions result in the formation of (Z)-beta,?-unsaturated ketones with excellent enantioselectivities and high Z-selectivities or (E)-beta,?-unsaturated ketones with high optical purities and excellent E-selectivities, depending on the silyl group used.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Zhuang Ni, Ran Sun, Jihong Wu, Chao Xu, Jinwen Huang, Fanhong Wu
Summary: The novel indium-mediated difluoroalkylation of iododifluoromethyl ketones with alpha, beta-unsaturated ketones provides a significant route to access 1,2-addition product with excellent regioselectivity. This method has a wide substrate scope, high efficiency, and mild reaction conditions. Furthermore, it can be applied to the synthesis of difluoro derivatives of biologically active molecules containing unsaturated ketone structures, serving as potentially valuable fluorinated intermediates in drug discovery.
Article
Chemistry, Physical
Xue Yang Wang, Qing Bao Zhang, Xiao Ling Jin, Li Zhu Wu, Qiang Liu
Summary: An unprecedented catalytic system has been developed for the one-pot synthesis of oxazole acetals from N-propargylamides and alcohols using diselenides, Selectfluor, and visible light. This system demonstrates excellent compatibility of visible-light promotion with organocatalytic oxidative carbon-oxygen bond formations, using air as the terminal oxidant.
Article
Chemistry, Physical
Jian He, Zhi-Qin Bai, Pan-Feng Yuan, Li-Zhu Wu, Qiang Liu
Summary: Substrates in excited state differ significantly from the corresponding ground state, making photocatalytic systems increasingly popular for activation of substrates. By optimizing the properties of photosensitizers, a series of iridium complexes with high performance were successfully designed for various challenging photocycloaddition reactions.
Article
Chemistry, Organic
Yong-Liang Ban, Long You, Kai-Wen Feng, Fei-Cen Ma, Xiao-Ling Jin, Qiang Liu
Summary: The mild and broadly applicable protocol described enables the preparation of a diverse array of multisubstituted alpha-selenoenals and -enones from easily accessible propargylic alcohols and diselenides. The transformation proceeds via the Selectfluor-promoted selenirenium pathway, showing potential for practical application in gram-scale experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kui Dong, Chuang-Yuan Zhao, Xiao-Ju Wang, Li-Zhu Wu, Qiang Liu
Summary: A new method has been reported for the bioinspired synthesis of heterodimer neolignan analogs using single-electron oxidation and oxidative radical cross-coupling strategy, resulting in selective formation of heterodimer 8-5' or 8-O-4' neolignan analogs.
Article
Chemistry, Organic
Jian He, Qiang Liu
Summary: A highly efficient [2+2] cycloaddition between maleimides and unsaturated moieties has been developed utilizing a visible-light triplet sensitization mode for the direct synthesis of multifunctional 3-azabicyclo[3.2.0]heptane derivatives. This strategy overcomes previous obstacles such as limited substrate scope and undesired reaction pathways under harsh UV irradiation by selectively activating the maleimide functionality through energy transfer from a new photosensitizer.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Physical
Yong-Liang Ban, Long You, Tao Wang, Li-Zhu Wu, Qiang Liu
Summary: A metallaphotoredox catalysis protocol has been developed for the efficient dearomatization of indoles using readily available N-quinolyl benzamides under environmentally benign conditions. The reaction allows regioselective functionalization of indoles and provides a mild and economical approach to produce a diverse array of products. Preliminary mechanistic studies suggest a single-electron transfer process is involved, with a catalytically competent organometallic Co(bzac)(3) identified.
Article
Chemistry, Organic
Biao Yang, Kui Dong, Xiang-Sheng Li, Li-Zhu Wu, Qiang Liu
Summary: An environmentally friendly and highly diastereo-selective method for the synthesis of indanes has been developed using a metastable-state photoacid system containing catalytic protonated merocyanine (MEH). Under visible-light irradiation, MEH forms a metastable Spiro structure and releases protons, facilitating the formation of carbocations from benzyl alcohols. This method allows for the easy synthesis of diverse molecules, mainly indanes, in the presence of various nucleophiles, with water being the only byproduct.
Article
Chemistry, Organic
Tao Wang, Yuan-Yuan Zong, Wan-Zhong Feng, Li-Zhu Wu, Qiang Liu
Summary: We report an unprecedented visible-light-mediated approach to generating aryl acyl radicals from readily available triazine esters. This mild and redox-neutral protocol allows for the synthesis of a diverse array of oxindoles attached to alcohol groups in a single operation. The recycling of leaving groups and a range of visible-light-mediated reactions using triazine ester as an acyl radical precursor demonstrate the synthetic potential of this methodology.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Tao Huang, Pan-Feng Yuan, Kui Dong, Yuan-Yuan Zong, Can Liu, Rui-Heng Wang, Xiao-Ling Jin, Qiang Liu
Summary: An efficient Barton nitrite ester-type cyclization reaction was developed to synthesize benzo[d][1,2]oxazin-1-ones from N-ethyl-N-nitrosobenzamides. The reaction proceeded through the homogeneous cleavage of N-N bonds, generating a nitrogen-centered radical for intramolecular H-atom transfer (HAT) in a highly efficient manner. Interestingly, the N-nitrosobenzamides were first converted to γ-hydroxy oximes, followed by a nucleophilic attack to efficiently produce the desired benzo[d][1,2]oxazin-1-ones.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Biao Yang, Xue-Yang Wang, Xie-Tian Huang, Zhi-Yuan Liu, Xian Li, Tao Huang, Xiang-Sheng Li, Li-Zhu Wu, Ran Fang, Qiang Liu
Summary: Cross-coupling of C-(sp(3)) radicals is an important method for constructing C-(sp(3))-C-(sp(3)) bonds. Capturing open-shell radicals with metal catalysts can enhance the selectivity. In this study, a selective cross-coupling method using iridium and nickel catalysts is disclosed, which is applied to the synthesis of alkyl-alkyl cross-coupled products. The method is also demonstrated for late-stage functionalization of drugs, natural products, and biomolecules.
Article
Chemistry, Organic
Kui Dong, Yi-Lin Zhao, Xiao-Ling Jin, Qiang Liu
Summary: A photocatalyzed oxidative dehydrogenative annulation method is presented, which allows for the synthesis of various indole-fused benzoxepines using atom-efficient strategies at room temperature. This method not only avoids the use of stoichiometric amounts of oxidants, but also exhibits excellent atom economy by generating H2O as the sole theoretical byproduct.
Article
Chemistry, Multidisciplinary
Tao Huang, Yuan-Yuan Zong, Tao Huang, Xiao-Ling Jin, Li-Zhu Wu, Qiang Liu
Summary: Visible-light-promoted site-selective and direct C-F bond functionalization of polyfluorinated iminosulfides allows the synthesis of gamma-lactams with a fluoro- and perfluoroalkyl-substituted carbon centre. The reaction shows high chemoselectivity control and excellent functional group tolerance.
Article
Chemistry, Physical
Genping Meng, Liping Zhen, Shihao Sun, Jun Hai, Zefan Zhang, Dina Sun, Qiang Liu, Baodui Wang
Summary: This study demonstrates a simple and versatile method to grow CsPbX3 perovskite quantum dots into ordered mesopores, forming emission-tunable antennas with enhanced photoluminescence quantum yield and thermal stability. By tailoring the halogen component, the emission spectra of embedded perovskite quantum dots were precisely tuned, showing excellent catalytic activity in photochemical reactions.
JOURNAL OF MATERIALS CHEMISTRY A
(2021)
Article
Chemistry, Organic
Pan-Feng Yuan, Tao Huang, Jian He, Xie-Tian Huang, Xiao-Ling Jin, Chunlin Sun, Li-Zhu Wu, Qiang Liu
Summary: The study presents a photosensitization strategy to introduce the unique triplet state reactivity of N-nitrososulfoximides into aryl alkene feedstocks, leading to functionalization of the compounds with both N-centered sulfonamidyl radical and nitric oxide functionalities. The method is mild, atom economical, and exhibits broad functional group tolerance. Additionally, the methodology is compatible with both terminal and internal 1,3-dienes, providing regio- and Z/E-selective 1,2-amidoximation products.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Kui Dong, Xiao-Ling Jin, Shihao Chen, Li-Zhu Wu, Qiang Liu
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
