Article
Chemistry, Multidisciplinary
Alexia N. Kim, Aurapat Ngamnithiporn, Michael D. Bartberger, Brian M. Stoltz
Summary: The first asymmetric trans-selective hydrogenation of 1,3-disubstituted isoquinolines has been developed, resulting in enantioenriched trans-tetrahydroisoquinolines in good yield with high enantioselectivity. Mechanistic studies reveal the crucial role of non-coordinating chlorinated solvents and halide additives in enabling trans-selectivity.
Article
Chemistry, Organic
Guiying Xiao, Chaochao Xie, Qianling Guo, Guofu Zi, Guohua Hou, Yuping Huang
Summary: A highly efficient asymmetric hydrogenation method has been developed for the synthesis of chiral gamma-hydroxy acid derivatives. The method shows excellent enantioselectivity and has the potential to be applied in the synthesis of chiral compounds and key intermediates for pharmaceutical synthesis.
Article
Chemistry, Multidisciplinary
Jun Zhu, Yue Zhang, Zeyu Wen, Qiyi Ma, Yongtao Wang, Jia Yao, Haoran Li
Summary: In this study, a highly efficient ruthenium-catalyzed semi-hydrogenation reaction of CO2-derived ureas was reported, resulting in the production of recyclable amines and formamides with high yields (up to 97%). This method shows good substrate applicability and could serve as a sustainable alternative for the hydrogenation of CO2 to formamides in the presence of amines. Furthermore, a new pathway for rapid hydrogenation of urea derivatives even at lower H2 pressure (<5 bar) has been discovered, providing new insights into the reduction functionalization of CO2 to form new C-N bonds.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Catherine Gazolla Santana, Michael J. Krische
Summary: Catalytic carbonyl reductive couplings facilitated by hydrogenation, transfer hydrogenation, and hydrogen autotransfer allow unsaturated hydrocarbons to substitute organometallic reagents for C-C bond formation without the need for stoichiometric metals, addressing issues of safety and challenges in large-scale implementation.
Article
Chemistry, Organic
Yu Nie, Qianjia Yuan, Feng Gao, Masahiro Terada, Wanbin Zhang
Summary: An efficient iridium-catalyzed double asymmetric hydrogenation of 2,5-dialkylienecyclopentanones is reported, delivering chiral 2,5-disubstituted cyclopentanones in excellent yields and stereoselectivities. The results suggest that the two C=C bonds were hydrogenated in a stepwise manner and the second stereocenter was controlled by the chiral catalyst and the chirality of monohydrogenated product. The hydrogenated products can be prepared on a gram-scale and are easily derivatized.
Article
Chemistry, Organic
Yu Nie, Qianjia Yuan, Feng Gao, Masahiro Terada, Wanbin Zhang
Summary: Herein, we report an efficient iridium-catalyzed double asymmetric hydrogenation of 2,5-dialkylienecyclopentanones, delivering the chiral 2,5-disubstituted cyclopentanones in excellent yields and stereoselectivities. The results of the kinetic experiments and control experiments indicated that the two C=C bonds were hydrogenated in a stepwise manner and the second stereocenter was synergistically controlled by the chiral catalyst and the chirality of monohydrogenated product. The hydrogenated products can be prepared on a gram-scale and are easily derivatized.
Article
Chemistry, Physical
Julie Heron, David Balcells
Summary: Copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a versatile reaction in click chemistry, and this study using density functional theory (DFT) revealed a single concerted step mechanism for the reaction. The research also showed that the formation of 1,4-triazole isomer of the product is selective, highlighting the flexible nature of the bonding within the coordination sphere of the bimetallic core of the catalyst.
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, Inorganic & Nuclear
Zheng Wang, Ning Ma, Xiaochi Lu, Ming Liu, Tian Liu, Qingbin Liu, Gregory A. Solan, Wen-Hua Sun
Summary: A series of manganese(i) carbonyl complexes with structurally related NN- and NNN-chelating ligands were synthesized and used as catalysts for transfer hydrogenation. The NN-systems based on N-R functionalized 5,6,7,8-tetrahydroquinoline-8-amines showed the highest catalytic activity in the conversion of acetophenone to 1-phenylethanol. The N-isopropyl derivative, Mn1, when combined with t-BuONa, achieved efficient reduction of acetophenone and various carbonyl substrates, with high TON values (up to 17,200; TOF of 3550 h(-1)). These findings support an outer-sphere mechanism for the hydrogen transfer and provide a sustainable alternative for producing alcoholic products from carbonyl substrates.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Organic
Ze Wang, Xianghua Zhao, Shiliang Wang, An Huang, Yifan Wang, Jiaying He, Fei Ling, Weihui Zhong
Summary: The asymmetric hydrogenation catalyzed by iridium/f-diaphos L1, L5 or L12 was successfully demonstrated for the first time, affording chiral alcohols with high conversions and moderate to excellent enantioselectivities. The protocol could be easily scaled up to gram-scale with a Turnover Number (TON) of 9700.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Materials Science, Biomaterials
Hao-Chi Hao, Gang Zhang, Ru Sun, Yu-Jie Xu, Jian-Feng Ge
Summary: Four 1,8-naphthyridine derivatives (1a-1d) with different organelle targeting abilities were synthesized. The optical properties of the derivatives were characterized, showing a red-shift of fluorescence emission with increasing system polarity. Colocalization imaging experiments confirmed the organelle-targeting capabilities of the derivatives and their ability to monitor organelle polarity fluctuation. This work proposes a new molecular design idea for developing polarity-sensitive fluorescent probes with organelle targeting.
JOURNAL OF MATERIALS CHEMISTRY B
(2023)
Article
Chemistry, Multidisciplinary
Xinting Liang, Minjin Yoo, Tabitha Schempp, Saki Maejima, Michael J. Krische
Summary: By utilizing a series of complex synthetic methods, the key substructures of neaumycin B were successfully synthesized, which possess potent inhibitory activity against glioblastoma.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Taiga Yasuda, Yusuke Yoshigoe, Shinichi Saito
Summary: This paper reports a concise synthesis of 1,8-diaminonaphthalene-protected diboronic acid (B2(dan)2), which is a promising borylating agent. B2(dan)2 is a stable compound that can be used for Cu-catalyzed borylation of styrene derivatives. The reaction shows high selectivity, and the products have yields up to 97%. Mechanistic studies suggest that a borate species is a key intermediate for the borylation reaction.
Review
Chemistry, Medicinal
Madhwi Ojha, Divya Yadav, Avinash Kumar, Suman Dasgupta, Rakesh Yadav
Summary: The 1,8-naphthyridine nucleus is a significant nitrogen-containing heterocyclic compound with versatile biological activities. Different research groups worldwide have developed synthesized 1,8-naphthyridine derivatives with a wide range of biological properties.
MINI-REVIEWS IN MEDICINAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Jose B. de Araujo-Neto, Maria M. C. da Silva, Cicera D. de M. Oliveira-Tintino, Ieda M. Begnini, Ricardo A. Rebelo, Luiz E. da Silva, Sandro L. Mireski, Michele C. Nasato, Maria I. L. Krautler, Jaime Ribeiro-Filho, Abolghasem Siyadatpanah, Polrat Wilairatana, Henrique D. M. Coutinho, Saulo R. Tintino
Summary: This study evaluated the antibacterial and antibiotic-modulating activities of 1,8-naphthyridine derivatives against multi-resistant bacterial strains. While the compounds themselves had no direct antibacterial activity, they were able to potentiate the activity of fluoroquinolone antibiotics, indicating a potential for synergism in combating multidrug resistant bacterial infections.
Article
Chemistry, Multidisciplinary
Wenpeng Ma, Jianwei Zhang, Cong Xu, Fei Chen, Yan-Mei He, Qing-Hua Fan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Multidisciplinary
Zhusheng Yang, Fei Chen, Yanmei He, Nianfa Yang, Qing-Hua Fan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Organic
Huan-Li Sun, Fei Chen, Ming-Sheng Xie, Hai-Ming Guo, Gui-Rong Qu, Yan-Mei He, Qing-Hua Fan
Article
Chemistry, Organic
Zhusheng Yang, Ziyuan Ding, Fei Chen, Yan-Mei He, Nianfa Yang, Qing-Hua Fan
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Yi-Yong Huang, Zong-Chao Lv, Xing Yang, Zhao-Lei Wang, Xiao-Xue Zou, Zhen-Ni Zhao, Fei Chen
Article
Chemistry, Organic
Zhusheng Yang, Fei Chen, Shuxin Zhang, Yanmei He, Nianfa Yang, Qing-Hua Fan
Article
Chemistry, Multidisciplinary
Zi-Yuan Ding, Fei Chen, Jie Qin, Yan-Mei He, Qing-Hua Fan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2012)
Article
Chemistry, Multidisciplinary
Tianli Wang, Fei Chen, Jie Qin, Yan-Mei He, Qing-Hua Fan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2013)
Article
Chemistry, Multidisciplinary
Fei Chen, Tianli Wang, Yanmei He, Ziyuan Ding, Zhiwei Li, Lijin Xu, Qing-Hua Fan
CHEMISTRY-A EUROPEAN JOURNAL
(2011)
Article
Chemistry, Multidisciplinary
Tianli Wang, Lian-Gang Zhuo, Zhiwei Li, Fei Chen, Ziyuan Ding, Yanmei He, Qing-Hua Fan, Junfeng Xiang, Zhi-Xiang Yu, Albert S. C. Chan
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2011)
Article
Chemistry, Organic
Jie Qin, Fei Chen, Ziyuan Ding, Yan-Mei He, Lijin Xu, Qing-Hua Fan
Article
Chemistry, Organic
Fei Chen, Ziyuan Ding, Jie Qin, Tianli Wang, Yanmei He, Qing-Hua Fan
Article
Chemistry, Organic
Fei Chen, Ziyuan Ding, Yanmei He, Jie Qin, Tianli Wang, Qing-Hua Fan
Article
Chemistry, Multidisciplinary
Tingting Miao, Zi-You Tian, Yan-Mei He, Fei Chen, Ya Chen, Zhi-Xiang Yu, Qing-Hua Fan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)