Article
Chemistry, Physical
Lantao Liu, Fangyuan Cheng, Chenxiang Meng, An-An Zhang, Mingliang Zhang, Kai Xu, Naoki Ishida, Masahiro Murakami
Summary: A Pd-catalyzed chemo-, regio-, and enantioselective ring-closing/ring-opening cross coupling reaction has been developed with diverse aryl halide-tethered alkenes and benzocyclobutenols as substrates. This method provides a convenient approach to chiral 2,3-dihydrobenzofurans with excellent enantioselectivities, and has been applied in the concise synthesis of analogues of cannabinoid receptor 2 agonists.
Review
Chemistry, Multidisciplinary
You Wang, Yuli He, Shaolin Zhu
Summary: Migratory cross-coupling via metal migration is a significant process in academic and industrial fields, providing an attractive alternative for the synthesis of challenging structures. This Account outlines recent progress and developments in the field, including migration-functionalization modes, diverse functionalizations, and strategies for regio- and stereocontrol.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Organic
Jihong Xu, Xuexiang Ma, Chengbu Liu, Dongju Zhang
Summary: Density functional theory calculations were used to investigate the mechanism and influencing factors of gold-catalyzed 1,2-diarylation reactions of alkenes.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhan Dong, Qiongyao Tang, Changyu Xu, Li Chen, Haiting Ji, Sitian Zhou, Liangliang Song, Liang-An Chen
Summary: Transition-metal catalyzed intermolecular 1,2-diarylation of electronically unactivated alkenes is a widely studied topic, but most examples are limited to terminal alkenes. Furthermore, the asymmetric 1,2-diarylation of unactivated alkenes remains unsolved and is challenging. In this study, a highly efficient directed nickel-catalyzed reductive 1,2-diarylation of unactivated internal alkenes with high diastereoselectivities is described. Moreover, enantioselective 1,2-diarylation of unactivated terminal and challenging internal alkenes is achieved with good to high enantioselectivities and high diastereoselectivities by generating a cationic Ni-catalyst through the addition of alkali metal fluoride.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jun Chen, Yu-Jie Liang, Peng-Zi Wang, Guo-Qing Li, Bin Zhang, Hao Qian, Xiao-Die Huan, Wei Guan, Wen-Jing Xiao, Jia-Rong Chen
Summary: This study presents a photoinduced copper-catalyzed cross-coupling reaction for the generation of allylic esters. The reaction proceeds at room temperature with high regio- and enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Yifan Wang, Yuanyuan Ping, Wangqing Kong
Summary: A cooperative Pd/Cu-catalyzed three-component cross-coupling reaction of alkynes, B 2 Pin 2 and alkenetethered aryl halides is reported. This reaction proceeds under mild conditions and shows broad substrate scope, providing a variety of heterocycles containing tetrasubstituted alkenylboronate moieties in synthetically useful yields with excellent chemoselectivity and regioselectivity. An enantioselective cascade cyclization/cross-coupling process has also been developed for the synthesis of enantiomerically enriched oxindole bearing a tetrasubstituted alkenylboronate moiety.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Applied
Lin Fan, Xinlong Yan, Changjiang Li, Yuxue Cao, Guodu Liu
Summary: In this study, a Cu-catalyzed intramolecular borylation-cross coupling reaction was developed, enabling the synthesis of both racemic and chiral borylated indolines. The reaction involved the simultaneous construction of C-C and C-B bonds using a Cu/phosphine ligand system. The method exhibited good to excellent yields and short reaction times. Asymmetric synthesis was also investigated, resulting in the successful synthesis of a chiral borylated indoline compound.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Jingwen Su, Wenbin Guo, Yi Liu, Lichun Kong, Hanliang Zheng, Gangguo Zhu
Summary: A copper-catalyzed, redox-neutral cascade difluoroalkylation/5-endo annulation/beta-fluorine cleavage of ynones is reported, providing a direct and stereoselective method to access synthetically important alpha-monofluoroalkenyl cyclopentanones. Mechanistic studies reveal an unprecedented Cu-II-assisted beta-fluorine fragmentation, which may have valuable implications for challenging but important C-F bond activation. Additionally, the in situ generated difluorocarbene is found to act as an effective reductant for the regeneration of copper(I) catalyst, eliminating the need for external reductants.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Bo Li, Cheng-Wei Ju, Wenlong Wang, Yanwei Gu, Shuai Chen, Yongrui Luo, Haozhe Zhang, Juan Yang, Hai-wei Liang, Mischa Bonn, Klaus Mu''llen, William A. Goddard, Yazhou Zhou
Summary: The study reports a heterogeneous single-atom Pt-catalyzed Heck reaction, the first of its kind on SACs, using a supercritical carbon-dioxide-assisted protocol. The research showcases how SACs can introduce underexplored coordination structures, offering potential for transferring migratory-insertion-based reactions to heterogeneous SACs.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Mathieu Morency, Radu Iftimie, Shawn K. Collins
Summary: This study discusses the mechanism of copper-catalyzed C-Sp-S cross-coupling to form rare macrocyclic alkynyl sulfides. Computational studies suggest that the reaction pathway involves the formation of Cu-S species followed by alpha-addition/elimination at the ethynylic carbon to afford the desired macrocycle.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kirsten A. Hewitt, Claire A. Herbert, Elizabeth R. Jarvo
Summary: A nickel-catalyzed intramolecular conjunctive cross-electrophile coupling reaction has been developed for the synthesis of 3,5-vicinal carbocyclic rings found in various biologically active compounds and natural products. Mechanistic experiments suggest that the reaction proceeds through alkyl iodides formed in situ, initiates at the secondary electrophilic center, and proceeds via radical intermediates.
Article
Chemistry, Organic
Muhammad Siddique Ahmad, Zahid Shafiq, Kamel Meguellati
Summary: In this study, a mild and selective cross dehydrogenative coupling (CDC) method mediated by Cu(I) was developed. Commercial low-cost unactivated alkenes and tetrahydrofuran derivatives were used as the source of ether and solvent, resulting in the synthesis of alpha-functionalized cyclic ethers. The method exhibited excellent selectivity and yield and can be applied to a wide range of aromatic alkenes, heteroaromatic alkenes, and cyclic ethers, providing valuable insights for the design of versatile alkenyl cyclic ethers.
Article
Chemistry, Multidisciplinary
Gyumin Kang, Sunkyu Han
Summary: In this study, we successfully synthesized dimeric high-oxidation-state securinega alkaloid Flueggeacosine B via two synthetic routes. The second-generation synthesis was more streamlined and a new reaction was developed to provide a direct pathway for the synthesis of compounds with a conjugated dicarbonyl moiety.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Nan-Quan Jiang, Tian-Shu Wu, Min Pan, Zhong-Jian Cai, Shun-Jun Ji
Summary: A novel palladium-catalyzed regioselective diarylation/deamination of homoallylamines is described, where a free amine is used as the directing group and removed in situ to form a unique tetraarylbutadiene motif. This chelate-controlled Heck-type approach eliminates the need for preinstalled and hard removable directing groups, proceeds under simple conditions, and exhibits good tolerance to a wide range of functional groups commonly found in organic synthesis.
Article
Chemistry, Multidisciplinary
Shentong Xie, Yuqing Yin, Ya Wang, Jiannan Wang, Xiaoqian He, Ruopeng Bai, Renyi Shi
Summary: The electroreductive cross-electrophile coupling is a powerful, green, and efficient method for constructing challenging C-C bonds, which has attracted increasing attention from organic chemists. Most of the previous works focus on direct two-electrophile cross-coupling. In this work, a nickel-catalyzed three-electrophile electroreductive cross-electrophile coupling has been developed, offering a direct and convergent synthesis to target molecules from easily available and cheap substrates under mild conditions.
Article
Chemistry, Multidisciplinary
Yuan Huang, M. Kevin Brown
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Multidisciplinary
Allison M. Bergmann, Stephen R. Sardini, Kevin B. Smith, M. Kevin Brown
ISRAEL JOURNAL OF CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Erin N. Hancock, Erin L. Kuker, Dean J. Tantillo, M. Kevin Brown
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Review
Polymer Science
Wei You, Kevin J. T. Noonan, Geoffrey W. Coates
PROGRESS IN POLYMER SCIENCE
(2020)
Article
Chemistry, Organic
Wei You, Kristina M. Hugar, Ryan C. Selhorst, Megan Treichel, Cheyenne R. Peltier, Kevin J. T. Noonan, Geoffrey W. Coates
Summary: Understanding the degradation mechanisms of organic cations under basic conditions is crucial for the development of durable alkaline energy conversion devices. An evaluation of 26 model compounds is being conducted to identify cations with improved alkaline stabilities and advance the field.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Polymer Science
Yin Zhang, Ting Wang, Jing Bai, Wei You
Summary: The article proposes a generic strategy using widely available starting materials (i.e., poly(ethylene-co-vinyl acetate), EVA) and mild Mitsunobu functionalization conditions to prepare over 30 polyethylene derivatives, without using noble transition metal catalysts or corrosive/explosive reagents. Functional groups such as azide, aldehyde, norbornene, and thiol can be easily installed with tunable content as high as 18 mol %. This practical method successfully prepared polyethylene-derivatized membranes with excellent antimicrobial and fluorescent properties.
Article
Energy & Fuels
Hongying Tang, Kang Geng, Lei Wu, Junjie Liu, Zhiquan Chen, Wei You, Feng Yan, Michael D. Guiver, Nanwen Li
Summary: Researchers have developed a new type of fuel cell membrane that can operate over a wider temperature range, from -20 to 200 degrees C. This ultramicroporous membrane retains phosphoric acid even under highly humidified conditions and exhibits higher proton conductivity retention compared to conventional membranes. This innovation could simplify heat and water management in fuel cell systems, potentially reducing costs.
Article
Chemistry, Physical
Guixiang Wang, Haitao Zou, Zhizhao Xu, Ao Tang, Fangfang Zhong, Xiaobo Zhu, Chengpeng Qin, Mei Ding, Wei You, Chuankun Jia
Summary: A redox flow battery system with improved energy density and low capital cost is demonstrated by unlocking the solubility limit of ferrocyanide. The proposed alkaline zinc-iron RFB features excellent electrochemical performance and reduced electrolyte cost, showing potential for commercial energy storage.
MATERIALS TODAY ENERGY
(2022)
Article
Polymer Science
Ting Wang, Yin Zhang, Yu Wang, Wei You
Summary: In this study, we propose a novel method to conveniently produce a series of PE-based AEMs with functional groups using commercial EVA. The synthesized membranes exhibit outstanding chemical stability, good alkaline stability, and high ion conductivity.
Article
Chemistry, Multidisciplinary
Jing Bai, Yu Wang, Wei You
Summary: This study proposes a novel method for synthesizing POE analogues with well-defined alkyl branches via ring-opening metathesis polymerization. By overcoming the challenges in defining the distribution and length of branches in traditional POE synthesis, this approach provides a new platform for studying the influence of branches on the properties of POEs.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Polymer Science
Yin Zhang, Yu Wang, Wei You
Summary: Novel macromolecular UV-absorbers with PE backbones and ferrocene side groups are synthesized based on derivatization of commercial EVA. The polymers show potential as UV absorbers and exhibit almost zero migration behavior within the PE matrix.
JOURNAL OF APPLIED POLYMER SCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Wei You, Jacob M. Ganley, Brian G. Ernst, Cheyenne R. Peltier, Hsin-Yu Ko, Robert A. DiStasio, Robert R. Knowles, Geoffrey W. Coates
Summary: A novel method for preparing high-performance AAEMs through photocatalytic hydroamination reaction is reported in this study, addressing the challenges of complex synthesis of functionalized cyclooctene monomers, while also considering the importance of local backbone morphology in the rational design of stable high-performance AAEMs.
Article
Polymer Science
Qi-ran Lu, Wei You
ACTA POLYMERICA SINICA
(2020)
Review
Biochemistry & Molecular Biology
Erin N. Hancock, Johannes M. Wiest, M. Kevin Brown
NATURAL PRODUCT REPORTS
(2019)
Article
Chemistry, Organic
Yuan Huang, Allison M. Bergmann, M. Kevin Brown
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)