Article
Chemistry, Organic
Gi Hoon Ko, Kyusik Um, Hee Chan Noh, Jin Young Kim, Haneal Jeong, Chanyoung Maeng, Sang Hoon Han, Gi Uk Han, Phil Ho Lee
Summary: Here, we demonstrate a regioselective acylmethylation of the cage B(4)-H bond in o-carborane acids using iridium(III) catalyst and sulfoxonium Aides under mild conditions. This reaction affords various B(4)-acylmethylated o-carboranes. Furthermore, by selectively conducting sequential B(4)- and B(6)-acylmethylation reactions, B(3,5)-diacylmethylated o-carboranes can be obtained in a one-pot manner.
Article
Chemistry, Multidisciplinary
Bartlomiej Sadowski, Binbin Yuan, Zhipeng Lin, Lutz Ackermann
Summary: In this study, electrocatalytic peri C-H alkenylation of 1-naphthols was achieved using rhodium(III) catalysis under constant current electrolysis conditions. This strategy offers a wide scope, good functional group tolerance, and high site- and stereoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Fangxiang Sun, Shuaimin Tan, Hou-Ji Cao, Chang-sheng Lu, Deshuang Tu, Jordi Poater, Miquel Sola, Hong Yan
Summary: This study reports three types of tricyclic compounds based on the fusion of three-dimensional aromatics and hydrocarbons, which can be used to prepare various functional molecules. These new compounds can be easily synthesized using Pd-catalyzed B-H activation and the cascade heteroannulation reaction. Computational results show that the newly generated rings have weak aromaticity, but they possess high thermal stability and photoluminescence efficiency.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Physical
Charles B. Musgrave, Weihao Zhu, Nathan Coutard, Jeffrey F. Ellena, Diane A. Dickie, T. Brent Gunnoe, William A. Goddard
Summary: In this study, we investigated the mechanism of oxidative conversion of benzene and ethylene to styrene using Cu(II) and Rh-Cu-Rh active catalyst. The incorporation of Cu(II) into the active Rh-Cu-Rh catalyst reduced the activation barrier for benzene C-H activation, O-H reductive elimination, and ethylene insertion into the Rh-Ph bond.
Article
Chemistry, Organic
Chanyoung Maeng, Gi Hoon Ko, Heejin Yang, Sang Hoon Han, Gi Uk Han, Hee Chan Noh, Kyungsup Lee, Dongwook Kim, Phil Ho Lee
Summary: A transition-metal-free synthetic method for o-carborane-fused pyrazoles has been developed, allowing twofold C-N bond formation under extremely mild conditions and high functional group tolerance. This method involves sequential diazotization and cyclization reactions in one pot using B(4)-acylmethyl or B(3,5)-diacylmethyl o-carborane and 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP) in the presence of DBU in acetonitrile.
Article
Chemistry, Organic
Alagumalai Ramkumar, Ramdas Sreedharan, Purushothaman Rajeshwaran, Thirumanavelan Gandhi
Summary: Here, we developed ruthenium(ii)-catalyzed oxidative dehydrogenation and hydroarylation of maleimides with phthalazinones. The product selectivity is controlled by the additives, and the hydroarylated product was obtained in water, which is an important highlight of this study. Control experiments suggest the occurrence of oxidative dehydrogenation pathway over E2-type elimination - the key step in producing Heck-type products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Applied
Ji Yang, Changjun Chen, Haoqiang Zhao, Bohan Li, Zhenni He, Lijin Xu, Qian Shi
Summary: Rh(III)-catalyzed chelation-assisted C8-selective C-H alkenylation and alkylation of 1,2,3,4-tretrahydroquinolines with styrenes and allylic alcohols have been achieved using a cationic Rh(III) catalytic system. The reaction proceeds with oxygen as the terminal oxidant and shows good substrate scope and functional group compatibility, providing the corresponding products in moderate to high yields. The choice of N-directing group is crucial for the catalysis, and the N-(2-pyrimidyl) group proves to be the optimal choice. Preliminary mechanistic studies have been conducted to gain insights into the reaction mechanism.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Biao Cheng, Yu Chen, Peng Zhou, Zuowei Xie
Summary: A new method for the trifunctionalization of o-carboranes has been developed, leading to the synthesis of a new class of B(3,4,5)-trisubstituted o-carborane derivatives. This method involves a series of reactions and represents a new strategy for the catalytic selective polyfunctionalization of carboranes with different substituents, achieving high yields of the desired products.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Chan Li, Yanchen Yang, Feifei Fang, Chaoyi Liu, Chunpu Li, Dechuan Wang, Hong Liu
Summary: In this study, a Rh(III)-catalyzed C-H activation strategy of N-nitrosoanilines and iodonium ylides was developed to construct novel tetralydrocarbzol-4-one scaffolds, providing valuable templates for sequential C-H functionalization at the C-5 position. Gram-scale synthesis and further transformations of tetralhydrocarbzol-4-one derivatives demonstrated the utility of this protocol in the concise and diverse construction of biologically active molecules.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Biao Cheng, Yu Chen, Zuowei Xie
Summary: An efficient iridium-catalyzed formal [4+2] annulation of carboranyl carboxylic acids with alkynes has been developed, allowing for the facile synthesis of a new class of carborano-isocoumarin derivatives. The carboxyl group not only acts as a directing group for regioselectivity control but also cleverly becomes a part of the final products. The reaction mechanism involves sequential carboxyl-directed B(4)-H metalation, alkyne insertion, and reductive elimination.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Devesh Manisha, Devesh Chandra, Upendra Sharma
Summary: An efficient Rh(III)-catalyzed C-H alkenylation of N-protected isoquinolone with maleimides is demonstrated, where the carbonyl group of isoquinolone acts as an inherent directing group. Various N-substituents in the maleimide, including alkyl, aryl, and even H and -OH, were well tolerated. This protocol exhibits broad substrate scope, good selectivity, and excellent yields, with the effect of substituents on the reaction progress confirmed by Hammett plot.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Liming Zhang, Ru Zhao, Chunhui Liu, Zhaoyang Li, Jun-Long Niu, Hao-Ran Yang, Lijun Gao, Shuang-Liang Liu, Liming Zhou
Summary: The Rh(III)-catalyzed ortho alkylation of N-pyridylcarbazoles with nitroalkenes has been developed for the synthesis of a wide range of 2-(2nitroalkyl)carbazoles. Aromatic and aliphatic nitroalkenes both successfully participated in this alkylation reaction. The protocol also worked well with an indoline based substrate. Derivatization of the representative nitroalkane product was described.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Jiajie Li, Xin Xu, Zhenli Luo, Zhen Yao, Ji Yang, Xin Zhang, Lijin Xu, Peng Wang, Qian Shi
Summary: Cp*Rh(III)-catalyzed regioselective C-H annulation and alkenylation of 2-pyridones with terminal alkynes has been developed, providing efficient access to diversified compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Chenyang Guo, Zaozao Qiu, Zuowei Xie
Summary: Carboranes, three-dimensional analogues of benzene, have wide applications and the recent development of transition-metal-catalyzed cage B-H functionalization allows for vertex-specific functionalization, providing valuable insights for future multifunctionalization of carboranes.
Article
Chemistry, Multidisciplinary
Yixiu Ge, Zaozao Qiu, Zuowei Xie
Summary: A palladium-catalyzed selective tetrafunctionalization method for o-carborane derivatives has been developed, providing 3,6-dialkenyl-4,11-R-2-o-carboranes and 4,7-dialkenyl-5,11-R-2-o-carboranes in moderate to excellent yields. This study represents a new strategy for the selective synthesis of polyfunctionalized o-carborane derivatives in a one-pot process.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Lingyao Wang, Yuanbin Zhang, Jia Yao, Haoran Li
Summary: Metal-free aerobic oxidation of aryl sulfides to sulfoxides and sulfones has been developed with excellent selectivity and yields in the presence of aliphatic aldehydes. The reaction proceeds under mild conditions with the catalysis of N-hydroxyphthalimide (NHPI), and control experiments indicated a free radical pathway involving acylperoxyl radicals as key intermediates.
Article
Chemistry, Multidisciplinary
Rajesh Varkhedkar, Fan Yang, Rakesh Dontha, Jianglin Zhang, Jiyong Liu, Bernhard Spingler, Stijn van der Veen, Simon Duttwyler
Summary: The identification of an alternative chemical space is crucial for discovering novel antimicrobial lead compounds to address the global challenge of antimicrobial resistance. Boron clusters are being explored due to their unique properties, but their synthesis and derivatization techniques have limitations. A new method was developed to rapidly construct a library of molecules and evaluate their antibacterial activity.
ACS CENTRAL SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Yunjia Jiang, Jianbo Hu, Lingyao Wang, Wanqi Sun, Nuo Xu, Rajamani Krishna, Simon Duttwyler, Xili Cui, Huabin Xing, Yuanbin Zhang
Summary: In this study, a new metal-organic framework (ZNU-2) was developed for efficient separation of propyne and propylene. The performance of the framework was tested under different conditions through simulations and experiments, demonstrating excellent recyclability and high productivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Mustapha Hamdaoui, Fan Liu, Yann Cornaton, Xingyu Lu, Xiaohuo Shi, Huan Zhang, Jiyong Liu, Bernhard Spingler, Jean-Pierre Djukic, Simon Duttwyler
Summary: This study reports on the activation of hydroborane by a new iridium boron cluster complex, leading to the formation of a stable boron cation. The reaction involves an unconventional intramolecular B center dot center dot center dot H interaction, and a mechanism is proposed based on theoretical methods and noncovalent interactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Yongqi Hu, Yunjia Jiang, Jiahao Li, Lingyao Wang, Mathias Steiner, Rodrigo F. Neumann, Binquan Luan, Yuanbin Zhang
Summary: The study introduces a new generation of anion-pillared metal-organic frameworks (MOFs) that can be used for capturing CO2 from flue gas. The optimized design of TIFSIX-Cu-TPA shows high CO2 capacity, excellent CO2/N-2 selectivity, high thermal and chemical stability, and moderate adsorption heat for easy regeneration. Breakthrough experiments under various process conditions demonstrate the practical separation performance of the synthesized MOFs, achieving highly selective separation and sustained outstanding performance even under high humidity and multiple process cycles. In situ CO2 dosed single crystal structure and theoretical calculations reveal the molecular mechanism of CO2 adsorption in MOFs, highlighting the presence of two separate binding sites for CO2 in small and large cages, contributing to the high performance of the newly designed MOFs.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Article
Engineering, Environmental
Wushuang Lou, Jiahao Li, Wanqi Sun, Yongqi Hu, Lingyao Wang, Rodrigo F. Neumann, Mathias Steiner, Zonglin Gu, Binquan Luan, Yuanbin Zhang
Summary: This study experimentally screens a new metal organic framework (MOF) material, Ni-Pz, which shows excellent performance in the separation of C2H2 from CO2, with high capacity, selectivity, stability, and recyclability. The Ni-Pz MOF is a promising candidate for industrial applications.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Engineering, Environmental
Nuo Xu, Jianbo Hu, Lingyao Wang, Dong Luo, Wanqi Sun, Yongqi Hu, Dongmei Wang, Xili Cui, Huabin Xing, Yuanbin Zhang
Summary: In this study, a novel metal organic framework material called ZNU-4 with unique topology was reported for selective acetylene (C2H2) capture. The material exhibited high adsorption capacity and selectivity for C2H2, making it suitable for C2H2 separation and recovery.
CHEMICAL ENGINEERING JOURNAL
(2022)
Article
Chemistry, Inorganic & Nuclear
Nuo Xu, Tongan Yan, Jiahao Li, Lingyao Wang, Dahuan Liu, Yuanbin Zhang
Summary: Researchers have successfully prepared a novel microporous compound ZNU-7, which shows excellent adsorption separation ability for acetylene and carbon dioxide. It has high adsorption capacity, easy desorption and regeneration properties.
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Engineering, Environmental
Yongqi Hu, Lingyao Wang, Ruihan Nan, Nuo Xu, Yunjia Jiang, Dongmei Wang, Tongan Yan, Dahuan Liu, Yuanbin Zhang, Banglin Chen
Summary: In this study, a pair of isoreticular cost-effective and stable MOFs (CAU-10-H and CAU-10-Py) were prepared for SF6/N2 separation, and CAU-10-Py showed remarkable improvement in SF6 uptake capacity and selectivity, making it a highly promising candidate for SF6 capture.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Applied
Jiahao Li, Lingyao Wang, Yuxin Chen, Zonglin Gu, Tao Jiang, Binquan Luan, Rajamani Krishna, Yuanbin Zhang
Summary: A series of water stable fluorinated anion pillared metal-organic frameworks (MOFs) were reported, which can efficiently capture and separate xenon from krypton with high selectivity and adsorption capacity, making them suitable for the separation of these gases in industry.
MICROPOROUS AND MESOPOROUS MATERIALS
(2023)
Article
Chemistry, Inorganic & Nuclear
Chuhao Lin, Yujie Jin, Jizeng Sun, Zehua Ye, Tao Chen, Jiyong Liu, Simon Duttwyler
Summary: Penta-iodination of the B2-6 positions of the CB11 monocarborane cluster was achieved for the first time. The product structures were fully characterized and confirmed by X-ray crystal structures. The synthetic method relied on palladium catalysis/B-H activation, assisted by the C1-COOH directing group. This one-pot procedure enables penta-iodination and subsequent decarboxylation under convenient conditions, showing complementary regioselectivity compared to commonly observed reactivity of CB11 clusters.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Yunjia Jiang, Lingyao Wang, Jianbo Hu, Rajamani Krishna, Banglin Chen, Yuanbin Zhang
Summary: This article reports a novel metal-organic framework CuZrF6-TPA for efficient separation of propyne and propadiene. The framework exhibits high propyne capacity and separation selectivity, allowing for high-purity propadiene production.
ADVANCED MATERIALS
(2023)
Article
Engineering, Chemical
Yuxin Chen, Yunjia Jiang, Jiahao Li, Xianghao Hong, Haofei Ni, Lingyao Wang, Nan Ma, Mingman Tong, Rajamani Krishna, Yuanbin Zhang
Summary: Efficient separation of CH4 from natural gas containing C2H6 and C3H8 impurities is crucial. Previous studies focused on C3H8/CH4 selectivity while neglecting the importance of C2H6/CH4 selectivity, leading to decreased CH4 productivity and compromised separation efficiency. In this study, a synergistic thermodynamic-kinetic selectivity for C3H8/CH4 and C2H6/CH4 was achieved using TIFSIX-Cu-TPA, surpassing most popular materials. Computational insights revealed a counteractive thermodynamic-kinetic relationship and determined precise adsorption sites of C2H6 and C3H8.
Article
Chemistry, Inorganic & Nuclear
Wanqi Sun, Yujie Jin, Yilian Wu, Wushuang Lou, Yanbin Yuan, Simon Duttwyler, Lingyao Wang, Yuanbin Zhang
Summary: A novel microporous boron cluster pillared metal-organic framework BSF-10 was synthesized and showed high selectivity and capacity for the separation of acetylene from carbon dioxide and ethylene.
INORGANIC CHEMISTRY FRONTIERS
(2022)