Article
Chemistry, Organic
Shuto Kosuge, Yusuke Araki, Kiyoshi Tsuge, Kenji Sugimoto, Yuji Matsuya
Summary: The one-pot de novo synthesis of pentasubstituted pyridines is achieved through Au-(I)-autotandem catalysis and subsequent aromatization. This process involves aza-enyne metathesis with aryl propiolates to yield 1-azabutadienes and their addition/6 pi-electrocyclization sequence with the other propiolate units. The resulting 1,4-dihydropyridines are aromatized to produce pyridines in the presence of atmospheric oxygen. The aryl propiolates are regioselectively incorporated into the ring system, leading to the formation of 2-arylpyridines as the sole product.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Binsen Rong, Gaochen Xu, Huan Yan, Sai Zhang, Qinghuan Wu, Ning Zhu, Zheng Fang, Jindian Duan, Kai Guo
Summary: An efficient copper-catalyzed annulation of ketoxime acetates with acetoacetanilide has been developed for the synthesis of benzofuro- and benzothieno[2,3-c]pyridines, showing good functional group tolerance and operational simplicity. Mechanistic investigation revealed the involvement of an ionic pathway rather than a radical pathway in the transformation.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Binsen Rong, Gaochen Xu, Huan Yan, Sai Zhang, Qinghuan Wu, Ning Zhu, Jindian Duan, Kai Guo
Summary: A copper-catalyzed [3+2]-type condensation reaction of alpha,beta-unsaturated ketoximes with activated ketones was described for the synthesis of dihydrooxazoles, especially trifluoromethyl-decorated dihydrooxazoles. This method is characterized by its broad substrate scope, good functional group tolerance, and simple operation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Jian-Shu Wang, Yi Na, Jun Ying, Xiao-Feng Wu
Summary: The cobalt-catalyzed regioselective cycloaddition of diynes and alkynes allows for the construction of structurally diverse substituted 1,3-dihydroisobenzofurans with excellent yields and regioselectivities.
MOLECULAR CATALYSIS
(2021)
Article
Chemistry, Organic
Changyuan Zhang, Huosheng Guo, Lulu Chen, Jiantao Zhang, Mengping Guo, Xuncheng Zhu, Chan Shen, Zeng Li
Summary: An economical and efficient protocol for the direct construction of amino skipped diynes has been described, achieving up to 83% yield of various symmetrical and asymmetrical 3-amino diynes under mild conditions through a one-pot reaction.
Article
Chemistry, Organic
Debasmita Mondal, Subhendu Pramanik, Chinmay Chowdhury
Summary: Palladium-catalyzed reactions provide an easy access to desired compounds, and the choice of suitable phosphine ligands is crucial for the success of the reaction.
Article
Biochemistry & Molecular Biology
Alexandra S. Bubnova, Daria V. Vorobyeva, Ivan A. Godovikov, Alexander F. Smol'yakov, Sergey N. Osipov
Summary: An efficient method for accessing CF3-containing spiro-[indene-proline] derivatives has been developed through a Cp*Rh(III)-catalyzed tandem C-H activation/[3+2]-annulation reaction between 5-aryl-2-(trifluoromethyl)-3,4-dihydro-2H-pyrrole-2-carboxylates and alkynes. Remarkably, the dehydroproline moiety acts as a directing group, enabling selective activation of aromatic C-H bond.
Article
Chemistry, Organic
Guzhou Chen, Peng-Yu Liu, Huanhuan Zou, Jiadong Hu, Xiaowu Fang, Dongyang Xu, Yu-Peng He, Hongbo Wei, Weiqing Xie
Summary: The study presents an Au(I)-catalyzed domino cyclization of 1,6-diynes incorporated with indole, leading to the diastereoselective formation of indole-fused azabicyclo[3.3.1]nonanes. Density functional theory calculations demonstrate an unprecedented cascade dearomatization/rearomatization/dearomatization process in the reaction, with noncovalent attractive interactions playing a role in the chemoselectivity of the initial spirocyclization step.
Article
Chemistry, Organic
Biao Nie, Wanqing Wu, Chuanfei Jin, Qingyun Ren, Ji Zhang, Yingjun Zhang, Huanfeng Jiang
Summary: A new synthetic protocol for alicyclic[b]-fused pyridines has been developed using a Pd(II)-catalyzed C-H activation/cyclization/aromatization strategy, allowing for the efficient and regioselective synthesis of a range of five- to eight-membered alicyclic[b]-fused pyridines in a one-step manner with broad substrate scope and good functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhongfeng Luo, Jingxing Jiang, Lifang Zou, Xiaoyu Zhou, Junshan Liu, Zhuofeng Ke, Fengjuan Chen, Huanfeng Jiang, Wei Zeng
Summary: The development of a Rh-catalyzed amine-directed remote 5,6-carboamination protocol of pyridines via dual Csp(2)-H functionalizations is disclosed in this study. Various readily available 2-aminopyridines and 1,2,3-triazoles can be coupled and cyclized to access polyfunctionalized azaindoles. Mechanistic studies reveal the involvement of relay carbenoid-electrophilic addition to pyridines and sequential pyridyl Csp(2)-H amination in this transformation. The post-synthetic utility of this methodology is demonstrated through versatile and site-selective modification of azaindoles.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Organic
Subhasree Pal, Siuli Das, Subhajit Chakraborty, Subhankar Khanra, Nanda D. Paul
Summary: In this study, a Zn(II)-catalyzed solvent-free sustainable synthesis of tri- and tetra-substituted pyridines was reported. The primary feedstock used was alcohols and NH4OAc served as the nitrogen source. The well-defined air-stable Zn(II)-catalyst, featuring a redox-active tridentate azo-aromatic pincer, was used for the synthesis of a wide variety of unsymmetrical 2,4,6-substituted pyridines by three-component coupling of alcohols with NH4OAc. The reactions proceeded efficiently and produced high yields of the desired products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shujun Cao, Chongchong Ma, Xinjie Teng, Rongshun Chen, Yun Li, Weidong Yuan, Yingguang Zhu
Summary: A novel and efficient synthesis method for fully substituted 1H-imidazoles has been developed through photoredox/copper cocatalyzed domino cyclization of oxime esters, aldehydes, and amines. This method exhibits good functional group tolerance, broad substrate scope, high step economy, high bond-forming efficiency, and the ability for gram-scale synthesis.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Panjie Hu, Lingfei Hu, Xiao-Xi Li, Mengxiao Pan, Gang Lu, Xingwei Li
Summary: This study reports the rhodium(I)-catalyzed hydroarylative cyclization of 1,6-diynes with three distinct classes of arenes, enabling highly enantioselective synthesis of a broad range of axially chiral 1,3-dienes that are conformationally labile. The experimental and computational studies reveal the detailed mechanistic aspects of the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Yan Zhang, F. Wieland Goetzke, Kirsten E. Christensen, Stephen P. Fletcher
Summary: In this study, we report an asymmetric catalytic method for the synthesis of YZJ-1139(1) and related compounds. By using a Rh-catalyzed reaction, a racemic N-Boc-nortropane-derived allylic chloride was coupled with (hetero)aryl boronic esters via an asymmetric Suzuki-Miyaura-type cross-coupling reaction, and an unexpected kinetic resolution was achieved. The enantiopure allyl chloride obtained can undergo highly enantiospecific reactions. This method was applied in the formal synthesis of YZJ-1139(1) with high stereoselectivity.
Article
Chemistry, Organic
Xi-Jie Dai, Paul Krolikowski, James I. Murray, Carolyn S. Wei, Peter K. Dornan, Andreas R. Rotheli, Seb Caille, Oliver R. Thiel, Austin G. Smith, Andrew T. Parsons
Summary: An efficient method for the synthesis of substituted pyridines through an organocatalyzed, formal (3+3) cycloaddition reaction is described. The reaction is accomplished using readily available enamines and enal/ynal/enone substrates, and yields tri- or tetrasubstituted pyridine scaffolds with a variety of functional groups. The method has been demonstrated on a 50 g scale, leading to the synthesis of 2-isopropyl-4-methylpyridin-3-amine, an important intermediate for the manufacture of sotorasib. Mechanistic analysis using two-dimensional NMR spectrometry revealed the formation of a stable reaction off-cycle species that precedes pyridine formation. In situ reaction progress kinetic analysis and control NMR studies were used to investigate the role of FeCl3 and pyrrolidine hydrochloride in promoting the reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Tengfei Li, Fen Xu, Xincheng Li, Chunxiang Wang, Boshun Wan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Organic
Tengfei Li, Hao Yan, Xincheng Li, Chunxiang Wang, Boshun Wan
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Yingying Zhao, Yancheng Hu, Haolong Wang, Xincheng Li, Boshun Wan
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Yingying Zhao, Haolong Wang, Xincheng Li, Dongping Wang, Xiaoyi Xin, Boshun Wan
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Organic
Yingying Zhao, Yancheng Hu, Chunxiang Wang, Xincheng Li, Boshun Wan
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Yingying Zhao, Yancheng Hu, Xincheng Li, Boshun Wan
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Chemistry, Organic
Hao Yan, Xincheng Li, Chunxiang Wang, Boshun Wan
ORGANIC CHEMISTRY FRONTIERS
(2017)
Article
Multidisciplinary Sciences
Chunxiang Wang, Gen Luo, Masayoshi Nishiura, Guoyong Song, Atsushi Yamamoto, Yi Luo, Zhaomin Hou
Article
Chemistry, Multidisciplinary
Yingying Zhao, Chunxiang Wang, Yancheng Hu, Boshun Wan
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Organic
Xiaodong Lu, Xiaoyi Xin, Boshun Wan
TETRAHEDRON LETTERS
(2018)
Article
Chemistry, Applied
Ruxia Yi, Xincheng Li, Boshun Wan
ADVANCED SYNTHESIS & CATALYSIS
(2018)
Article
Chemistry, Multidisciplinary
Xuemei Liu, Chaonan Cui, Shuoshuo Wei, Jinyu Han, Xinli Zhu, Qingfeng Ge, Hua Wang
Summary: This study presents a new strategy for designing efficient photocatalysts that can convert CO2 into hydrocarbons by utilizing synergistic catalytic sites. The findings provide a solution for the selective photocatalytic reduction of CO2 to CH4.
Article
Chemistry, Multidisciplinary
Chengxian Hu, Dan Wang, Lu Wang, Ying Fu, Zhengyin Du
Summary: A novel one-pot, three-component reaction conducted under electrochemical conditions was studied. The reaction involved 2-aminothiophenols, aldehydes, and malononitrile, using TBABF4 as an electrolyte and CuI as a catalyst. The proposed reaction mechanism suggested that CuI served as an electron relay. This method offers simplified operation, high atom economy, and mild reaction conditions.
Article
Chemistry, Multidisciplinary
Zhi Yang, Yu Chen, Linxi Wan, Yuxiao Li, Dan Chen, Jianlin Tao, Pei Tang, Fen-Er Chen
Summary: A highly enantioselective method for the complete hydrogenation of pyrimidinium salts using Ir/(S,S)-f-Binaphane complex as the catalyst was developed. This method provides easy access to fully saturated chiral hexahydropyrimidines, which are prevalent in many bioactive molecules. The reactions exhibit high yields and enantioselectivities under mild reaction conditions without additives. Successful application of this methodology in a continuous flow fashion further extends its practical utility.
Article
Chemistry, Multidisciplinary
Tina Jeoh, Jennifer Danger Nill, Wujun Zhao, Sankar Raju Narayanasamy, Liang Chen, Hoi-Ying N. Holman
Summary: In this study, the enzymatic hydrolysis of cellulose was investigated using real-time infrared spectromicroscopy. The spatial heterogeneity of cellulose was found to impact the hydrolysis kinetics. Hydration affected cellulose ordering, and Cel7A preferentially removed less extensively hydrogen bonded cellulose.
Article
Chemistry, Multidisciplinary
Tiphaine Richard, Walid Abdallah, Xavier Trivelli, Mathieu Sauthier, Clement Dumont
Summary: An effective method of grafting functionalities onto lignin based on glycerol carbonate has been developed using an efficient nickel-catalysed telomerisation reaction. This method allows lignin to have new reactive functions and reduces the glass transition temperatures of modified lignins, thereby expanding the application range of lignin-based resins.
Article
Chemistry, Multidisciplinary
Jing Qi, Xiyan Wang, Gan Wang, Srinivas Reddy Dubbaka, Patrick ONeill, Hwee Ting Ang, Jie Wu
Summary: This study presents a green and environmentally friendly approach for the synthesis of imides using electrocatalytic oxidation with H2O as the oxygen source. The method eliminates the need for toxic or expensive oxidants and achieves high yields under mild reaction conditions. It shows broad substrate compatibility and potential for industrial applications.
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang
Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.
Article
Chemistry, Multidisciplinary
Juho Antti Sirvio, Idamaria Romakkaniemi, Juha Ahola, Svitlana Filonenko, Juha P. Heiskanen, Ari Ammala
Summary: This article discusses the method of using supramolecular interaction between an aromatic hydrogen bond donor and lignin to achieve rapid delignification of softwood at low temperatures.
Article
Chemistry, Multidisciplinary
Yunyan Meng, Chunxiang Pan, Na Liu, Hongjiang Li, Zixiu Liu, Yao Deng, Zixiang Wei, Jianbin Xu, Baomin Fan
Summary: A novel visible light-driven synthesis method for 2,3-diamines has been developed, which has mild conditions, avoids the use of metal reagents, and can synthesize diamines and diols in one pot.
Article
Chemistry, Multidisciplinary
Mingqing Huang, Haiyang Huang, Mengyao You, Xinxin Zhang, Longgen Sun, Chao Chen, Zhichao Mei, Ruchun Yang, Qiang Xiao
Summary: A direct air-oxidized strategy for the synthesis of benzo[b]phosphole oxides was developed in this study. Arylphosphine oxides were transformed into phosphinoyl radicals, which were further combined with various alkynes to achieve the desired products. DFT calculations revealed the mechanism of phosphinoyl radical formation.
Article
Chemistry, Multidisciplinary
Anwei Wang, Jiayin Huang, Chunsheng Zhao, Yu Fan, Junfeng Qian, Qun Chen, Mingyang He, Weiyou Zhou
Summary: This study demonstrates an innovative strategy for the aerobic oxidation of C(sp(3))-H bonds using gamma-valerolactone. By optimizing the reaction conditions and utilizing specific catalysts, efficient oxidation of C(sp(3))-H bonds is achieved with good chemoselectivity in certain cases.
Article
Chemistry, Multidisciplinary
Shun Li, Likai Tong, Zhijian Peng, Bo Zhang, Xiuli Fu
Summary: Sulfide compounds show promise as electrocatalysts for water splitting, but their performance is limited by factors such as limited active sites and hindered substance transport. This study successfully prepared a high-entropy sulfide (ZnCoMnFeAlMg)(9)S-8, which reduced grain size and increased specific surface area, enabling the realization of a dual-functional catalyst with multiple catalytic sites. High entropy also modulated the electronic properties of sulfides, reducing the potential energy barrier for hydrolysis. This research introduces a new approach for functionalizing high entropy nanomaterials and improves the performance of water splitting catalysts.
