Article
Chemistry, Multidisciplinary
Chen-Yan Cai, Yun-Tao Zheng, Jing-Fu Li, Hai-Chao Xu
Summary: A scalable Cu-electrocatalytic alkene diazidation reaction with 0.02 mol % of copper(II) acetylacetonate as a precatalyst without exogenous ligands has been reported. This electrocatalytic method is characterized by low catalyst loading, scalability, compatibility with a wide range of functional groups, and applicability to various types of alkene diazidation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Rongxiang Chen, Yaoxue Tang, Xiaohui He, Kai-Kai Wang, Lina Ding, Lantao Liu
Summary: A copper/cobalt-catalyzed difunctionalization of alkenes with sulfonylazides and tert-butyl hydroperoxide has been developed for the efficient synthesis of β-ketosulfones and β-sulfonyl peroxides. This protocol offers moderate to good yields under mild conditions and features a wide substrate scope and good functional group tolerance. Sulfonylazides are used as a new sulfonyl radical source in this methodology.
Article
Chemistry, Organic
Xuan Zhan, Guiqi Gao, Yating Liang, Fengyi Li, Ke Liu, Weigang Fan, Sheng Zhang, Man-Bo Li
Summary: Herein, we report a 'green' aminochlorination method of alkenes using acetonitrile and MgCl2 as nitrogen and chlorine sources, respectively. Benzimidazole was used as a reactivity modulator for chlorine radicals, achieving tunable reactivity, chemoselectivity and stereoselectivity in the four-component reaction.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Jixin Wang, Donghao Luo, Ying Hu, Zhili Duan, Jianlin Yao, Konstantin Karaghiosoff, Jie Li
Summary: Simultaneous formation of carbon-carbon and carbon-heteroatom bonds through transition metal-catalyzed alkene difunctionalization is a powerful tool for synthetic organic chemistry. A new type of S- and P-stabilized bromoallenes for palladium-catalyzed modular allenation and borylation of alkenes has been developed, enabling the synthesis of multiply functionalized allenes in a highly selective manner. This method offers broad substrate scope and functional group compatibility, allowing for the facile installation of allenyl and boryl groups across alkenes.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zhong Zhang, Yang Tian, Xiaowei Li, Zemin Wang, Ruihua Liu, Ping Chen, Xiangqian Li, Jiajia Dai, Dayong Shi
Summary: The difunctionalization of unsaturated compounds is advantageous for the construction of multiple functional groups simultaneously. In this study, we successfully introduced acyl and trifluoromethylthio groups into compounds using S-trifluoromethyl thioesters as bifunctional reagents. This method allows for the synthesis of various β- and δ-trifluoromethylthiolated ketones with broad functional group compatibility.
Article
Chemistry, Multidisciplinary
Shiwei Lu, Zipeng Wang, Xiang Gao, Kai Chen, Shifa Zhu
Summary: This study presents a method for directly inserting acetylene into readily available bifunctional reagents, resulting in high regio- and stereoselective synthesis of diverse C2-linked 1,2-bis-heteroatom products and opening up new synthetic directions. The synthetic potential of the method was demonstrated by converting the obtained products into various functionalized molecules and chiral sulfoxide-containing bidentate ligands. The mechanism for this insertion reaction was investigated using a combination of experimental and theoretical methods.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Stanislav A. Paveliev, Oleg O. Segida, Andrey Dvoretskiy, Mark M. Dzyunov, Uliana Fedorova, Alexander O. Terent'ev
Summary: A novel electrochemical process was developed for the difunctionalization of vinyl arenes with N-hydroxyphthalimide, resulting in vicinal dioxyphthalimides. The reaction involves the anodic generation of stabilized phthalimide-N-oxyl radical, which adds to the carbon-carbon double bond of vinyl arenes and recombines with the subsequently formed benzylic radical to afford a wide range of dioxyphthalimides with yields up to 81%.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Huili Li, Jianmin Fu, Jundong Fu, Xueji Li, Donglei Wei, Hou Chen, Liangjiu Bai, Lixia Yang, Huawei Yang, Wenxiang Wang
Summary: A visible-light metal-free photocatalytic regioselective and enantioselective alkene halofunctionalization reaction under mild conditions is described. Various terminal and internal alkenes could be transformed to α-halogenated and α,β-dibrominated derivatives with good to excellent yields in as short as 5 min reaction time. Water serves as the green nucleophile and solvent in halohydroxylation and halo oxidation reactions. Different types of products can be obtained by adjusting the reaction conditions. Moreover, sunlight demonstrates the ability to produce similar yields, showcasing a practical example of solar synthesis and offering an opportunity for solar energy utilization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Satoshi Minakata, Hayato Miwa, Kenya Yamamoto, Arata Hirayama, Sota Okumura
Summary: This study demonstrates the stereospecific, substrate-controlled intermolecular anti- and syn-1,2-diaminations of unactivated alkenes using an iodine catalyst. The combined use of the two methods allows access to all diastereomeric forms of 1,2-diamines, even in the presence of E- and Z-alkenes, with the resulting products easily convertible into free vicinal diamines.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Yang Xi, Wenyi Huang, Chenchen Wang, Haojie Ding, Tingting Xia, Licheng Wu, Ke Fang, Jingping Qu, Yifeng Chen
Summary: This study reports a new catalyst system for the enantioselective transformation of internal acyclic alkenes. By applying different reaction types to two common acyclic alkenes, products with asymmetric centers were obtained. Moreover, the formation of incontiguous stereocenters was achieved through an interrupted chain-walking process.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Multidisciplinary Sciences
Shengzhang Liu, Shengchun Wang, Pengjie Wang, Zhiliang Huang, Tao Wang, Aiwen Lei
Summary: This article reports an electro-oxidative method for the 1,2-amino oxygenation of alkenes without the need for additional oxidants. This method offers a cheap, scalable, and efficient route for the synthesis of valuable beta-amino alcohol derivatives. The method also shows broad substrate scope and potential for application in continuous-flow reactors, as well as the possibility for further amino-functionalization reactions of alkenes.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Hong-Li Ruan, Yun-Xia Deng, Zi-Jing Li, Sheng-Yin Zhao
Summary: By employing a catalyst and oxidant, a three-component radical selenosulfonation reaction of substituted maleimides, sulfonyl hydrazides, and diphenyl diselenides was realized, providing a series of 3,4-selenosulfonylated succinimides in moderate to good yields. This reaction demonstrates broad substrate scopes, high functional group tolerability, and the feasibility of gram-scale synthesis, allowing for one-step construction of C-SO2 and C-Se bonds under mild reaction conditions. Preliminary mechanistic studies support a free-radical-induced pathway.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Dylan E. Holst, Celine Dorval, Casey K. Winter, Ilia A. Guzei, Zachary K. Wickens
Summary: Modular strategies are valuable in synthesis for rapidly increasing molecular complexity. Transformation of an alkene into a dielectrophile allows the introduction of two unique nucleophiles. Unfortunately, the selectivity profiles of known dielectrophiles have hindered this approach.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Chemistry, Multidisciplinary
Helin Wang, Alex Adonis Nkingwa, Fawad Islam, Chao Xu, Qingle Zeng
Summary: Organochalcogen molecules have extensive applications in various fields. The difunctionalization of olefins is a successful technique for introducing two functional moieties in a single-step reaction. The combination of olefins with diorganyl dichalcogenides effectively increases molecular complexity.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Xiaoshuo Wang, Shubing Shu, Xiaojing Wang, Renshi Luo, Xiayi Ming, Tao Wang, Zhenming Zhang
Summary: A facile electrochemical method for the synthesis of cyclic ethers from linear unsaturated alcohols and sulfonyl hydrazides has been developed. This catalyst-free protocol involves electro-oxidation, radical addition, and intramolecular oxygen nucleophilic processes. The methodology is compatible with a wide range of substrates and functional groups, offering a convenient synthetic tool for the preparation of saturated oxygen heterocycles. Additionally, the electrochemical system can also convert linear unsaturated acids into lactones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Shi-Hui Shi, Yujie Liang, Ning Jiao
Summary: Selective C-C bond cleavage using electrochemical methods has been identified as a sustainable and scalable strategy that shows potential in replacing chemical reagents with electricity. Progress in this area has been made, with more examples of C-C bond cleavage via different maneuvers being developed recently, showcasing the exciting potential of electrochemical synthesis.
Article
Chemistry, Physical
Yujie Liang, Shi-Hui Shi, Rui Jin, Xu Qiu, Jialiang Wei, Hui Tan, Xue Jiang, Xiaomeng Shi, Song Song, Ning Jiao
Summary: This study introduces an electrocatalytic method for oxidation reactions using simple Ni(II)-bipyridine complexes, with water as the oxygen source. The electrochemical process generates active Ni(II)-peroxo species and O-2 for subsequent oxygenation reactions. This strategy may inspire the development of efficient nickel-catalyzed aerobic oxygenations and the exploration of transition-metal-based oxidation chemistry combined with electrochemistry.
Article
Chemistry, Physical
Zhichao Huang, Yuxuan Lin, Cheng Han, Yi-Yang Sun, Kai Wu, Wei Chen
Summary: In this study, the electronic properties of submonolayer Br on Cu(111) were investigated using scanning tunneling microscopy and DFT calculations. It was found that the local work function of Br islands ranged from 5.1 to 5.8 eV, with edge atoms exhibiting a lower work function than internal atoms, contrary to common intuition. This counterintuitive observation was attributed to the stabilization of charged internal Br by neighboring atoms.
JOURNAL OF PHYSICAL CHEMISTRY C
(2021)
Article
Chemistry, Physical
Bin Di, Zhantao Peng, Zhongyi Wu, Xiong Zhou, Kai Wu
Summary: The study explores the charge transfer between single atoms and their supports in several model systems. It found that Cs transfers more electrons than K, while gold and bromine atoms draw electrons from supports.
JOURNAL OF MATERIALS CHEMISTRY A
(2022)
Article
Chemistry, Multidisciplinary
Junyi Zhou, Jinliang Pan, Yu Jin, Zhantao Peng, Zhen Xu, Qiwei Chen, Pengju Ren, Xiong Zhou, Kai Wu
Summary: This study differentiates the catalytic properties between cationic and metallic single atoms. The results show that on monolayered CuO support, the reaction mechanism for CO conversion to CO2 is Eley-Rideal for cationic Ni atoms, while it is Mars-van Krevelen for metallic Ni atoms and previously reported Au and Pt model catalysts.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Multidisciplinary Sciences
Weijun Guo, Junqing Yin, Zhen Xu, Wentao Li, Zhantao Peng, C. J. Weststrate, Xin Yu, Yurong He, Zhi Cao, Xiaodong Wen, Yong Yang, Kai Wu, Yongwang Li, J. W. Niemantsverdriet, Xiong Zhou
Summary: This study provides direct experimental evidence of the ethylene polymerization pathway at the molecular level. Through in situ visualization using scanning tunneling microscopy, it was observed that ethylene polymerization occurs on a specific triangular iron site at the boundary between two carbide domains. In the absence of an activator, a surface-anchored ethylidene serves as the chain initiator and grows through ethylene insertion.
Article
Chemistry, Physical
Yangjun Luo, Yanwei Wang, Xuetao Qin, Youyuan Wang, Kai Wu, Huijuan Zhang, Li Zhang, Heming Huang, Wu Tian, Yu Wang
Summary: A Pt/Ti4O7 single atom catalyst was synthesized by dispersing Pt atoms on the surface of nanoporous Ti4O7 using a one-step calcination method. The Pt/Ti4O7 SAC exhibited excellent activity and stability in oxygen reduction reaction.
JOURNAL OF CATALYSIS
(2022)
Article
Physics, Multidisciplinary
Yang He, Na Li, Ivano E. Castelli, Ruoning Li, Yajie Zhang, Xue Zhang, Chao Li, Bingwu Wang, Song Gao, Lianmao Peng, Shimin Hou, Ziyong Shen, Jing-Tao Lu, Kai Wu, Per Hedegard, Yongfeng Wang
Summary: Investigation of intermolecular electron spin interaction is fundamental in science and technology. In this study, radical pairs of all-trans retinoic acid molecules were created on Au(111) and antiferromagnetic coupling between two radicals was identified. The coupling is mediated through O-H hydrogen bonds.
PHYSICAL REVIEW LETTERS
(2022)
Article
Chemistry, Physical
Zhantao Peng, Bin Di, Xinwei Zhao, Yuxuan Lin, Mengxiao Diao, Zhen Xu, Weijun Guo, Xiong Zhou, Qiwei Chen, Yongfeng Wang, Kai Wu
Summary: The deposited picene molecules on a monolayered CuO film self-assemble into side-on molecular strips on Cu(110), forming two stacking modes and anchored to the Cu-O chains via their armchair edges.
JOURNAL OF PHYSICAL CHEMISTRY C
(2022)
Article
Chemistry, Physical
Xiaojie Wen, Jie Li, Yuxuan Lin, Mengxiao Diao, Wenhui Zhao, Bin Di, Zhantao Peng, Dan Liu, Xiong Zhou, Qiwei Chen, Yongfeng Wang, Jing Liu, Kai Wu
Summary: Through scanning tunneling microscopy and density functional theory studies, we reported a surface-confined bicomponent supramolecular structure with structural anisotropy. These findings provide insights into the mediation effect of the fine balance between the molecule-substrate and intermolecular interactions on the supramolecular structures, offering an efficient methodology for supramolecular anisotropical engineering.
JOURNAL OF PHYSICAL CHEMISTRY C
(2022)
Article
Chemistry, Physical
Yuxuan Lin, Mengxiao Diao, Jingxin Dai, Zhen Xu, Xinwei Zhao, Xiaojie Wen, Lingbo Xing, Xiong Zhou, Qiwei Chen, Jing Liu, Kai Wu
Summary: A molecular investigation reveals that Cu adatoms embedded in DCTP-Cu chains on Cu(111) surface are located at the hollow and bridge sites, leading to stepwise elimination of Cu adatoms in the chains. The interchain interaction plays an important role in the Cu-elimination process and promotes the cooperative Cu-elimination and C-C coupling of the OM segments in neighboring chains. These findings demonstrate the key role of molecule-substrate and intermolecular interactions in mediating the reaction processes of extended molecular systems on surfaces.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Multidisciplinary
Yujie Liang, Fritz Paulus, Constantin G. Daniliuc, Frank Glorius
Summary: We report a BF3-catalyzed [2 + 2] cycloaddition reaction between aldehydes and bicyclo[1.1.0]butanes (BCBs) to access polysubstituted 2-oxabicyclo[2.1.1]hexanes. A new BCB containing an acyl pyrazole group was discovered, which not only facilitates the reactions but also allows for diverse downstream transformations. Additionally, aryl and vinyl epoxides can be used as substrates that undergo cycloaddition with BCBs after in situ rearrangement to aldehydes. These results will promote the exploration of complex sp(3)-rich bicyclic frameworks and BCB-based cycloaddition chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Xiaoyan Bao, Dawei Lu, Zining Wang, Hao Yin, Biao Zhu, Bin Chen, Meixiang Shi, Yang Zhang, Qianxin Xu, Yumei Qin, Xing -Can Shen, Kai Wu
Summary: Using solar energy to convert CO2 into value-added chemicals has great potential to address global energy shortage and climate change. This study reports a novel strategy of preparing a boron-doped g-C3N4/TiO2-x composite catalyst (BCT) that shows extended full-spectrum absorption, rapid charge separation, and outstanding CO2 photoreduction performance. The CO2 conversion rate of BCT is 7.5 and 9.2 times higher than that of pure TiO2 and g-C3N4, respectively. Mechanistic studies reveal that the synergistic effects of BCT lower the energy barrier for CO2 conversion by altering charge density distribution. This work provides a new integrated strategy for fabricating efficient catalysts.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2023)
Article
Chemistry, Physical
Zining Wang, Yumei Qin, Yu Chen, Yuchen Zhang, Qiwei Chen, Xiong Zhou, Kai Wu
Summary: By designing and fabricating one-dimensional titanium dioxide photocatalysts and incorporating a Pt co-catalyst and oxygen vacancies, efficient transformation of ethanol into value-added 1,1-diethoxyethane has been achieved. This strategy shows high conversion rate, selectivity, and potential for widespread applications.
Article
Chemistry, Physical
Yujie Liang, Felix Strieth-Kalthoff, Peter Bellotti, Frank Glorius
Summary: This study presents a dual nickel/photoredox catalytic strategy for the transformation of α-amino acids into β-amino aldehydes, providing a new catalytic blueprint for one-carbon homologation without pre-functionalization steps. The mechanistic studies demonstrate the rapid access of aldehydes through capturing radicals in situ, potentially expanding the applications of other molecules for valuable aldehyde synthesis.
