Article
Chemistry, Multidisciplinary
David Egea-Arrebola, F. Wieland Goetzke, Stephen P. Fletcher
Summary: Rhodium-catalyzed enantioselective additions of aryl and vinyl boronic acids to cyclobutenone ketals are described in this work. The reaction involves enantioselective carbometalation to give cyclobutyl-rhodium intermediates, followed by beta-oxygen elimination to afford enantioenriched enol ethers. Overall, this addition serves as a surrogate for Rh-catalyzed 1,4-additions to cyclobutenone.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Feilong Sun, Chengxi Yang, Jie Ni, Gui-Juan Cheng, Xianjie Fang
Summary: A regiodivergent nickel-catalyzed hydrocyanation of 1-aryl-4-silyl-1,3-diynes is reported, where appropriate ligands result in high yields and regioselectivities of two different enynyl nitriles. DFT calculations show that different ligands lead to diverse alkyne insertion modes, impacting the regioselectivity. The synthetic value of cyano-containing 1,3-enynes is demonstrated through downstream transformations.
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, Applied
Hui Jiang, Chun-Yang Zhang, Jin-Kui Liu, Mao-Ping Song, Jun-Fang Gong
Summary: In this study, a catalytic enantioselective alkynylation reaction of trifluoropyruvates with 1,3-diynes was successfully achieved using C2-symmetric NCN pincer rhodium (III) complexes with bis(imidazolinyl)phenyl ligands. This method is effective for the enantioselective synthesis of optically active trifluoromethylated tertiary alcohols. Additionally, the catalytic reaction is applicable for the preparation of chiral CF3-containing conjugated diynols with high enantioselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Jian-Shu Wang, Qi Wang, Yiwen Zhu, Qian Gao, Jun Ying, Xiao-Feng Wu
Summary: A cobalt-catalyzed domino Pauson-Khand and [4 + 2] cycloaddition of substituted diynes has been developed for the rapid construction of complexed polycyclic ring systems. The reaction proceeded well using benzene-1,3,5-triyl triformate (TFBen) as the CO source, yielding various tetracyclic compounds with high yields, excellent regioselectivity, and diastereoselectivity. Control experiments were conducted to gain a better understanding of the reaction mechanism.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Physical
Jing-Jing Tang, Xiaoqiang Yu, Yoshinori Yamamoto, Ming Bao
Summary: A visible-light-promoted and simple iron salt-catalyzed N-arylation was efficiently achieved under external photosensitizer-free conditions. The method features high reactivity, wide substrate scope, and good functional group tolerance.
Article
Chemistry, Organic
Congcong Huang, Yubo Pang, Xiang-Ai Yuan, Yuan-Ye Jiang, Xiaoyu Wang, Peng Liu, Siwei Bi, Jin Xie
Summary: Selective hydroarylation of internal alkynes catalyzed by a dimeric manganese complex provides a powerful strategy for constructing multisubstituted alkenes. This study investigated the mechanism and origin of regiodivergent hydroarylation of internal alkynes and found that the interaction between the substrate and catalyst, as well as the deformation induced by sterically hindered groups, are responsible for the observed selectivity. The computational results provide important insights for further designing and adjusting the strategy in Mn-catalyzed alkyne hydroarylation.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Qing Wang, Hoimin Jung, Dongwook Kim, Sukbok Chang
Summary: This study presents a highly regioselective amidation reaction using metal-catalyzed olefin chain walking, with dioxazolones as the amino source. The reaction shows great selectivity for both simple alkenes and heteroatom-substituted olefins, providing a new strategy for terminal amidation of these compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Can-Ming Chen, Ye-Nan Yang, Yin-Zhu Kong, Bo-Han Zhu, Peng-Cheng Qian, Bo Zhou, Long-Wu Ye
Summary: One-carbon homologation reactions based on one-carbon insertion into the N-O bond of heterocycles have attracted significant attention. However, the use of hazardous and difficult-to-access diazo compounds as precursors and the absence of relevant asymmetric catalysis have posed challenges. In this study, a copper-catalyzed intermolecular formal (5 + 1) annulation of 1,5-diynes with 1,2,5-oxadiazoles was demonstrated to achieve one-carbon insertion into the heterocyclic N-O bond via a non-diazo approach. This method offers practical and efficient synthesis of valuable pyrrole-substituted oxadiazines under mild reaction conditions, and the possibility of asymmetric annulation also arises.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Galla Karunakar, Chittala Emmaniel Raju, Gottam Sreenivasulu, Perla Bharath Kumar, Veerabhushanam Kadiyala, Balasubramanian Sridhar
Summary: An efficient intramolecular cyclization reaction was developed to synthesize indenone derivatives. The gold-catalyzed organic transformation allowed the conversion of substituted 1,5-diyenes to the corresponding indenones, resulting in the formation of two C=O and one C-C bonds in one pot under mild reaction conditions, leading to moderate to excellent yields of the target molecules.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Xiaolei Ji, Chaoren Shen, Xinxin Tian, Kaiwu Dong
Summary: A palladium-catalyzed asymmetric hydroesterification reaction was developed for preparing chiral alpha-substituted succinates with moderate yields and high ee values. The kinetic profile of the reaction progress indicated that the alkene substrate underwent hydroesterification followed by esterification with alcohol. The enantioselectivity was elucidated by density functional theory computation.
Article
Chemistry, Organic
Jixing Lai, Chen Yang, Rene Csuk, Baoan Song, Shengkun Li
Summary: The first palladium-catalyzed asymmetric addition of arylboronic acids to coumarins has been successfully developed, providing a straightforward and asymmetric approach for the synthesis of pharmaceutically important 4-aryl-3,4-dihydrocoumarins. This methodology employs easily accessible and stable ligands, has a broad substrate scope, can be conducted under mild reaction conditions, and allows for the accommodation of electron-withdrawing arylboronic acids.
Article
Chemistry, Organic
Wei Wu, Beibei Luo, Yi You, Zhiqiang Weng
Summary: A novel synthesis approach for the construction of 2-trifluoroethyl-substituted benzofurans under copper-catalyzed conditions has been developed, with moderate to excellent yields (up to 93%). This method is also applicable to the formation of 2-trifluoroethylated indoles.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Xiaoting Gan, Fen Huang, Zhijun Ren, Bo Li, Shaojie Chen, Wenkun Luo, Jun Zhou
Summary: The synthesis of multi-substituted 1-aminoisoquinolines from aminopyridine pivalamides with alkynes by Rh(III)-catalyzed C-H activation coupling has been successfully achieved. This method is tolerant of various functional groups and provides moderate yields of highly substituted isoquinoline derivatives.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Zhanglin Shi, Xiaolei Ji, Chaoren Shen, Kaiwu Dong
Summary: With the aid of an innate amide group, a Pd-catalyzed enantioselective hydroamidocarbonylation reaction of alpha-substituted acrylamides was developed, and a series of chiral 2-substituted succinimides were obtained in moderate to high yields and enantioselectivities. The generality of this approach was demonstrated by the carbonylation of both aryl- and alkyl-substituted acrylamides containing numerous functional groups.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Materials Science, Multidisciplinary
Xiaohui Chen, Letao Huang, Yongguang Jia, Rong Hu, Meng Gao, Li Ren, Ben Zhong Tang
ADVANCED OPTICAL MATERIALS
(2020)
Article
Chemistry, Multidisciplinary
Minjie Zhang, Xin Jin, Meng Gao, Yunjiao Zhang, Ben Zhong Tang
Summary: A sensitive self-reporting immunogenic cell death (ICD) inducer targeting endoplasmic reticulum (ER) stress is developed. The inducer can rapidly generate reactive oxygen species (ROS) and unfolded protein response process, leading to the release of damage-associated molecular patterns and efficient dendritic cell maturation. The fluorescence signal of the inducer allows real-time monitoring of ER accumulation and stress induction.
ADVANCED MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Shuhui Dai, Maliang Tao, Yuan Zhong, Zixiong Li, Jianshu Liang, Dongcheng Chen, Kai Liu, Binbin Wei, Bo Situ, Meng Gao, Ben Zhong Tang
Summary: A series of easily prepared pyrroles that can quickly be transformed into red-to-NIR emissive radical cations in acidic buffer solution and in vivo stomachs have been developed. These in-situ-generated red-to-NIR emissive pyrrole radical cations in the stomach have excellent biocompatibility and stability, and can be used for intravital gastrointestinal imaging with high spatiotemporal resolution, dynamic monitoring of the gastric emptying process, and assessment of anti-gastric-acid therapy.
ADVANCED MATERIALS
(2023)
Article
Nanoscience & Nanotechnology
Chao Lu, Youzhen Li, Wenchao Zhu, Yan Yang, Kai Liu, Qingtao Li, Meng Gao
Summary: A self-monitoring theranostic probe TPATCF-S has been developed, which can release H2S quickly under water stimuli and monitor the release by a color change. The TPATCF-S absorbed on alginate dressings can be used for wound exudate-responsive release of H2S to efficiently promote skin wound healing.
ACS APPLIED BIO MATERIALS
(2023)
Article
Nanoscience & Nanotechnology
Wenping Pan, Hongwei Shao, Limin Ma, Xubo Tong, Zicong Zhang, Qian Li, Xin Yang, Kai Liu, Meng Gao, Yingjun Wang
Summary: Organelle-targeted therapy guided by fluorescence imaging holds great potential for precise cancer treatment. However, current therapies can only destroy single organelles, resulting in limited efficacy. To overcome this challenge, researchers have developed a photoactivatable probe that can sequentially destroy multiple organelles in cancer cells, including lysosomes, lipid droplets, and mitochondria. This probe not only eradicates cancer cells efficiently in vitro but also suppresses tumor growth in vivo. Moreover, the probe enables real-time observation of the sequential destruction of multiple organelles through green-to-red fluorescence conversion. This photoactivatable probe provides a new strategy for cancer treatment with greatly improved efficacy.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Organic
Shuang-Gui Lei, You Zhou, Li-Sheng Wang, Zhi-Cheng Yu, Ting Chen, Yan-Dong Wu, Meng Gao, An-Xin Wu
Summary: A novel multicomponent cascade cyclization reaction has been developed for the synthesis of pyrido[3,2-a]phenoxazin-5-ones using simple o-aminophenols, paraformaldehyde, and enaminones. The o-aminophenol serves as a bis-nucleophile and an iminoquinone precursor, facilitating the formation of aminophenoxazinones for the first time through the Povarov reaction, resulting in high-efficiency synthesis of pyrido[3,2-a]phenoxazin-5-ones. These compounds exhibit polarity sensitivity and aggregation-induced emission (AIE) characteristics, making them promising for bioimaging and theranostic applications.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Materials Science, Biomaterials
Yue Han, Jing Li, Lihua Zheng, Yunhua Chen, Yan Yang, Kai Liu, Yiyue Zhang, Meng Gao
Summary: Bacterial infections with emerging resistance to antibiotics require the development of new antibacterial agents. Researchers have reported a series of antibacterial agents based on positively charged organic groups that can selectively bind and destroy bacterial membranes. To achieve imaging-guided antibacterial therapy, these organic groups often need to be combined with imaging modalities. Researchers have successfully prepared positively charged and deep-red fluorescent supramolecular pyrrole radical cations, which can be used for selective imaging and killing of bacteria.
BIOMATERIALS SCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Zicong Zhang, Wenping Pan, Yayu Xie, Kai Liu, Meng Gao, Yingjun Wang
Summary: We have developed a photoactivatable fluorescent probe that enables tandem imaging of organelles and in situ monitoring of their interplay. This strategy offers the advantages of simple operation and significant fluorescence spectral difference, making it promising for studying organelle interplay in various biological processes.
MATERIALS CHEMISTRY FRONTIERS
(2022)
Article
Nanoscience & Nanotechnology
Xubo Tong, Dong Bian, Lijing Hao, Lin Wang, Limin Ma, Meng Gao, Yingjun Wang
Summary: A fluorescent probe has been developed for real-time monitoring of the corrosion processes of magnesium alloys in biophysiological media. This method shows excellent spatiotemporal resolution, which could greatly contribute to the clinical applications of magnesium alloy implants.
ACS APPLIED BIO MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Lihua Zheng, Wenchao Zhu, Zikai Zhou, Kai Liu, Meng Gao, Ben Zhong Tang
Summary: A new strategy for preparing red-to-NIR fluorophores from electron-rich 2,5-dimethylpyrroles through air oxidation and stabilization has been proposed, showing promising potential for biomedical applications in bio-imaging.
MATERIALS HORIZONS
(2021)
Article
Chemistry, Multidisciplinary
Minjie Zhang, Yongguang Jia, Meng Gao, Li Ren, Ben Zhong Tang
Summary: The study introduced a photo-triggered zinc ion release system, which can efficiently regulate zinc enzyme activities inside and outside cells, showing potential for regulating zinc enzymes and bioactivities.
MATERIALS CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Tao Zhou, Jianfang Zhu, Dan Shang, Chuxing Chai, Youzhen Li, Haiying Sun, Yongqin Li, Meng Gao, Min Li
MATERIALS CHEMISTRY FRONTIERS
(2020)
Article
Chemistry, Multidisciplinary
Xia Ling, Letao Huang, Youzhen Li, Qing Wan, Zhiming Wang, Anjun Qin, Meng Gao, Ben Zhong Tang
MATERIALS HORIZONS
(2020)
Article
Chemistry, Multidisciplinary
Jin Wang, Meng Gao, Zhong-Kai Cui, Yong-Guang Jia, Sa Liu, Kai-Feng Chen, Xiaohui Chen, Yiqing Zhang, Zhou Fang, Yunhua Chen, Kaojin Wang, Huatang Zhang, Lin Wang, Li Ren
MATERIALS CHEMISTRY FRONTIERS
(2020)
Article
Chemistry, Multidisciplinary
Xiaoxue Ge, Meng Gao, Bo Situ, Weiwei Feng, Bairong He, Xiaojing He, Shiwu Li, Zihao Ou, Yiqi Zhong, Yahui Lin, Xinyi Ye, Xiumei Hu, Ben Zhong Tang, Lei Zheng
MATERIALS CHEMISTRY FRONTIERS
(2020)
Article
Polymer Science
Paige A. Shaw, Maxime Klausen, Mark Bradley
Summary: A light-responsive polymer capable of controlled release of camptothecin and generation of reactive oxygen species (ROS) was developed, which exhibited high cancer cell killing activity through both camptothecin release and ROS generation.
Article
Polymer Science
Donghui Zhang, Shiqi Liu, Zhihao Cai, Weizhe Luo, Guojian Liu, Runhui Liu
Summary: A straightforward and efficient method for synthesizing NPC monomers has been developed in this study, which enhances the availability of NPC monomers and facilitates the synthesis of polypeptides.
