Article
Chemistry, Organic
Bo-Wei Huang, Jeng-Liang Han
Summary: A vinylogous addition reaction of allyl aryl ketones can be catalyzed by squaramide catalysts to give good yields and excellent regioselectivity. Chiral tertiary alcohols and bicyclic pyrrolidones can be synthesized in good to excellent yields, enantioselectivities, and diaseteroselectivities. Experimental and DFT calculations suggest that the reaction favors 1,2-addition at lower temperatures and 1,4-addition/cyclization at higher temperatures. Compound 4 may form through either the 1,4-addition/cyclization pathway or retro-aldol reaction of compound 3, followed by subsequent 1,4-addition/cyclization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhenqiang Chen, Yingying Sun, Shoufeng Wang, Qing-Wei Zhang
Summary: A base-promoted tandem Michael addition of malonates to 2,3-bis(diarylphosphinyl)-1,3-butadienes was developed for the synthesis of cyclopentyl 1,2-bisphosphine compounds. This method enables rapid construction of various 1,2-bis(diarylphosphinyl)cyclopentanes, and features readily accessible reactants, mild conditions and good functional group tolerance. The product could be easily transformed to the corresponding transition metal complexes, which may find broad applications in asymmetric catalysis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
John Kamanda Mansaray, Yekai Huang, Kuiliang Li, Xiang Sun, Zhenggen Zha, Zhiyong Wang
Summary: An efficient enantioselective Michael addition reaction of 2,3-dioxopyrrolidine with indole in aqueous media was developed by using a chiral copper complex. This reaction exhibits air tolerance, a wide substrate scope, and mild reaction conditions. Control experiments, XPS investigation, and DFT calculations support the proposed mechanism.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Engineering, Chemical
Zheng Wang, Pinye Zhao, Xianzhen Li, Qianqian Sun, Diao She
Summary: In this study, a potassium humate-based carbon material with good adsorption performance for phosphate was successfully prepared through modification and rapid pyrolysis. The material showed high adsorption capacity for phosphate under specific temperature and pH conditions, and the adsorption process followed classical adsorption kinetics and models. The main adsorption mechanisms involved various physical and chemical processes. Additionally, the material exhibited excellent regenerability.
JOURNAL OF THE TAIWAN INSTITUTE OF CHEMICAL ENGINEERS
(2022)
Article
Chemistry, Organic
Zhongxue Fang, Yu Wang, Yiming Ma, Xinyue Han, Zhaohong Liu, Yongquan Ning
Summary: This study presents the development of the Rh-catalyzed[2,3]-sigmatropic rearrangement of alkynyl carbenes with allyl sulfides. The protocol shows good tolerance towards various functional groups and enables the synthesis of valuable sulfide-substituted 1,5-enyne products. It is the first example of [2,3]-sigmatropic rearrangement of alkynyl carbenes. DFT analysis confirms the involvement of rhodium carbene generation, sulfoniumylides formation, and [2,3]-sigmatropic rearrangement pathway.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Kaizhi Li, Yixin Lu
Summary: Enantioselective gamma-addition of readily available alpha-substituted nitroacetates to allenoates has been achieved, providing a straightforward asymmetric synthesis of optically enriched alpha,alpha-disubstituted alpha-amino acid precursors. The reaction proceeds efficiently with high yields and good to excellent enantioselectivities in the presence of amino acid-derived phosphine catalysts, forming products containing a tetra-substituted stereogenic center.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Kilian Colas, A. Catarina V. D. dos Santos, Stefanie Kohlhepp, Abraham Mendoza
Summary: The addition of organometallic reagents to aliphatic carboxylic acids for the synthesis of ketones is limited to organolithium reagents, but can be extended to Grignard reagents using a bulky aniline-derived turbo-Hauser base. This method allows for the straightforward preparation of a variety of aliphatic and perfluoroalkyl ketones.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Cedric Spitz, Morgane Bertrand, Vincent Remusat, Thierry Terme, Patrice Vanelle
Summary: In this study, the intermolecular addition reaction of benzyl halides to aldehydes and imines was achieved using photoactivated TDAE as a super-photoreductant, leading to the formation of 3,4-dihydroisocoumarins, 1,2-diarylethanols, and 1,2-diarylcarbamates under simple, mild, and metal-free conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zheng-Jian Li, Ming-Yang Wang, Chu-Qiao Li, Wei-Long Zeng, Wei Li
Summary: Incorporating amino functionality into organic synthesis is highly important. In this study, we report an intermolecular dearomative aminofunctionalization by adding simple amines to chromium-bound arenes, allowing for the rapid synthesis of complex compounds containing amino and amide functionalities under CO-gas-free conditions. This work also demonstrates the first application of nitrogen-based nucleophiles in eta(6)-coordination-induced arene dearomatizations.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Construction & Building Technology
Xiujiang Pang, Li Chen, Yawen Shi, Yuan Meng, Xueyu Pang, Yanguang Yuan, Yuan Liu
Summary: This study found that the use of magnesium aluminum layered double hydroxides nanosheets can improve the water resistance and compressive strength of magnesium oxychloride cement.
CONSTRUCTION AND BUILDING MATERIALS
(2022)
Article
Chemistry, Physical
Qingqing Tu, Wenwen Liu, Meng Jiang, Wenjuan Wang, Qing Kang, Pengcheng Wang, Weijia Zhou, Feimeng Zhou
Summary: A NiFe-LDH catalyst with partially crystalline characteristics was synthesized, showing high catalytic activity and stability during seawater electrolysis. The presence of more boundaries in the partially crystalline NiFe-LDH contributes to its higher catalytic efficiency and stability in alkalized seawater.
ACS APPLIED ENERGY MATERIALS
(2021)
Article
Chemistry, Organic
Ramanjaneyulu Unnava, Kapil Chahal, Kallu Rajender Reddy
Summary: A concise method has been developed for the synthesis of substituted 1,2-dihydroisoquinolines via double nucleophilic addition of primary arylamines to ortho-alkynyl donor-acceptor cyclopropanes in the presence of a catalytic system. This method also allows for the conversion of some derived malonates into monoesters under specific reaction conditions, as well as the formation of multifunctionalized 4-(2,2,2-trifluoroacetyl) 1,2-dihydroisoquinolines with excess TFAA.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Yogesh Yadav, Rajdeep Tyagi, Kanchan Yadav, Ghanshyam Tiwari, Ram Sagar
Summary: The Ferrier rearrangement using SnCl4 as catalyst allows for the synthesis of 2,3-unsaturated glycopyranosides with high stereoselectivity starting from the hydroxyl group at the C-3 position. This method has several advantages, including strong anomeric selectivity, high yields, and short reaction time.
CARBOHYDRATE RESEARCH
(2023)
Article
Chemistry, Applied
Li-Fei Xiong, Li-Jiao Zhou, Ran Bu, Shuai-Liang Yang, En-Qing Gao
Summary: In this article, a facile approach to ionic MOFs with high halide content and improved catalytic activity is reported. The efficient azide-alkyne click reaction within the mesoporous MOF allows quantitative cationization of the linkers, resulting in bifunctional ionic MOFs that contain one halide ion per metal center.
MICROPOROUS AND MESOPOROUS MATERIALS
(2022)
Article
Engineering, Environmental
Xiaoqiang Cui, Jianwei Zhang, Minghui Pan, Qiang Lin, Muhammad Bilal Khan, Xiaoe Yang, Zhenli He, Beibei Yan, Guanyi Chen
Summary: Pyrolysis is a promising technique for the sustainable utilization of heavy metal hyperaccumulators from phytoremediation. This study found that high pyrolysis temperature and low PVC addition promoted the volatilization of Cd and Zn, while high PVC addition suppressed heavy metal volatilization. The addition of PVC increased biochar yield but also elevated Cd and Zn leaching, indicating a dual effect on heavy metal separation and biochar production.
JOURNAL OF HAZARDOUS MATERIALS
(2021)
Article
Chemistry, Multidisciplinary
Jieping Chen, Xuzhong Shen, Zhan Lu
Summary: A cobalt-catalyzed Markovnikov-type hydroboration method has been developed for the synthesis of alpha-alkenyl boronates with good regioselectivity and atom economy. The new ligand used with the cobalt hydride catalyst facilitates the selective insertion of terminal alkynes into metal hydride bonds. This protocol shows excellent tolerance to functional groups and delivers valuable alkene derivatives efficiently.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jiajing Li, Bing Yu, Zhan Lu
Summary: Imidazoline, as a structural analog of oxazoline, has gained significant attention in the rational design of chiral ligands due to its additional N-substituent allowing for fine-tuning of electronic and steric effects. Various chiral imidazoline ligands have been designed and employed in asymmetric organic reactions, expanding the applications of chiral synthesis.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Jun Guo, Zhaoyang Cheng, Jianhui Chen, Xu Chen, Zhan Lu
Summary: Transition metal-catalyzed asymmetric hydro-functionalization has been a straightforward and atom-economic way to access valuable optically active products. While noble transition metals have dominated this field, the attention has recently shifted to first-row, earth-abundant transition metals for their economic and sustainable advantages. However, the limited availability of chiral ligand libraries remains a significant challenge in developing highly enantioselective versions for these earth-abundant metal catalyzed reactions.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Zhaoyang Cheng, Jun Guo, Yufeng Sun, Yushan Zheng, Zhehong Zhou, Zhan Lu
Summary: This study presents a controllable cobalt-catalyzed sequential hydrosilylation/hydroboration reaction of arylacetylenes, achieving high regioselectivities for all possible regio-outcomes. Adjusting the ligands of cobalt catalysts combined with dual catalysis relay strategy is crucial for achieving regio-chemistry control, which may inspire further exploration in diversity-oriented synthesis involving multiple additions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Dongpo Lu, Peng Lu, Zhan Lu
Summary: A cobalt-catalyzed asymmetric reduction of β,β-dialkyl α,β-unsaturated esters using PMHS as a reductive reagent was reported, delivering esters with a chiral trialkyl carbon center at the β-position with high yield and high enantioselectivity. The chiral tridentate ligand OIP showed excellent performance in the asymmetric reduction, replacing the need for chiral bidentate ligands. This simple protocol utilizes readily available PMHS as a cost-effective and easy-to-handle reductive reagent for a wide range of substrates.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Peng Lu, Xiang Ren, Haofeng Xu, Dongpo Lu, Yufeng Sun, Zhan Lu
Summary: This study presents an iron-catalyzed highly enantioselective hydrogenation method for the synthesis of chiral alkanes from minimally functionalized 1,1-disubstituted alkenes. A novel chiral 8-oxazoline iminoquinoline ligand and its iron complex have been designed and synthesized to facilitate this transformation. The reaction is operationally simple, utilizing 1 atm of hydrogen gas, and demonstrates good functional group tolerance.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Tongtong Li, Xiaokai Cheng, Jiamin Lu, Huifeng Wang, Qun Fang, Zhan Lu
Summary: The asymmetric reductive arylation and alkenylation of benzylic chloride under photoredox/nickel dual catalysis using chiral BiIm ligand allows for the synthesis of 1,1-diaryl alkanes and aryl allylic compounds with good yield and stereo- and enantioselectivities. The method is compatible with various functional groups and shows promise in applications such as late-stage functionalization.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Wenbo Liu, Yushan Zheng, Yihui Mao, Jieping Chen, Xiang Ren, Zhaoyang Cheng, Zhan Lu
Summary: A cobalt-catalyzed desymmetrizing isomerization of exocyclic alkenes to generate chiral 1-methylcyclohexene derivatives with good yields and enantioselectivities was reported. A novel chiral thiazolinyl iminoquinoline ligand and its cobalt complex were designed and synthesized to control the establishment of tertiary or quaternary carbon centers at a remote position. This protocol is operationally simple, and a model for the stereochemical outcome has been proposed.
Article
Multidisciplinary Sciences
Yufeng Sun, Jun Guo, Xuzhong Shen, Zhan Lu
Summary: In this study, a method for sequentially catalyzing alkynes with nitrogen and silicon atoms using a cobalt catalyst is presented. The method involves two catalytic cycles with different ligands, and demonstrates high efficiency, simple operation, and excellent functional group tolerance. The study also reveals a phenomenon of ligand relay, where certain ligands can capture metal ions from other ligands.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Chenhui Chen, Hongliang Wang, Tongtong Li, Dongpo Lu, Jiajing Li, Xie Zhang, Xin Hong, Zhan Lu
Summary: A cobalt-catalyzed asymmetric sequential hydroboration/isomerization/hydroboration reaction of 2-aryl vinylcyclopropanes was reported for the first time, yielding valuable chiral 1,5-bis(boronates) with good yields and excellent enantioselectivity. The reaction protocol was successfully applied for the synthesis of (-)-preclamol and chiral 1,2,5-triaryl alkanes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jiajin Zhao, Guoxiong Xu, Xue Wang, Jiren Liu, Xiang Ren, Xin Hong, Zhan Lu
Summary: A cobalt-catalyzed multipositional isomerization of conjugated dienes using an 8-oxazoline iminoquinoline ligand has been reported. This reaction is simple and efficient, yielding disubstituted 1,3-dienes with good yields and stereoselectivity.
Article
Multidisciplinary Sciences
Jieping Chen, Jiale Ying, Zhan Lu
Summary: In this study, a cobalt-catalyzed selective hydroallylation reaction was developed to synthesize branched 1,4-dienes. The reaction exhibited excellent functional group tolerance and substrate scope, allowing for gram-scale reactions. The proposed mechanism was based on deuterium labeling experiment and kinetic studies.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Guan-Nan Li, Hao-Cong Li, Meng-Ru Wang, Zhan Lu, Bing Yu
Summary: A visible-light-induced acylation aromatization reaction of para-quinone methides to access alpha,alpha'-diarylated ketones using cheap and readily available carboxylic acids as acylating reagents via deoxygenation was developed. The method offers a simple and efficient approach to synthesis and shows a broad substrate scope, allowing for late-stage functionalization of drug molecules.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Peng Lu, Hongliang Wang, Yihui Mao, Xin Hong, Zhan Lu
Summary: Investigation on asymmetric hydrogenation of olefins is vital for the synthesis of pharmaceutical molecules and chemical industry. A cobalt-catalyzed enantioconvergent hydrogenation method has been developed for common minimally functionalized E/Z-olefin mixtures.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Guan-Nan Li, Hao-Cong Li, Zhan Lu, Bing Yu
Summary: The direct coupling of benzoxazoles and amines was achieved through visible light irradiation and CuCl catalysis. Various aminated benzoxazoles were synthesized successfully under mild conditions using air as an oxidant.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
