Article
Chemistry, Physical
Vidmantas Bieliunas, Sigitas Stoncius
Summary: The design and synthesis of second generation C-2-symmetric ligands with additional substituents was reported. These substituents provide a further element for fine-tuning the ligand structure by enforcing conformational rigidity. The tetrasubstituted bicyclo[3.3.1]nona-2,6-dienes were successfully employed in the rhodium-catalyzed arylation reaction with good to excellent yields and enantioselectivities up to 99% ee.
Article
Chemistry, Applied
Kenya Tamaribuchi, Jiaqi Tian, Kengo Akagawa, Kazuaki Kudo
Summary: Enantioselective Michael addition of beta-dicarbonyl compounds towards nitroalkenes was achieved using an immobilized, N-terminal-guanidinylated peptide catalyst. Various nucleophiles and electrophiles were employed, with the resin-supported catalyst being recyclable for five cycles. This method shows promise for industrial applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Saul Alberca, Marta Velazquez, Jose Trujillo-Sierra, Javier Iglesias-Siguenza, Rosario Fernandez, Jose M. Lassaletta, David Monge
Summary: Catalysts generated by combinations of Pd(TFA)(2) and pyridine-hydrazone ligands have been successfully applied to the addition of arylboronic acids to aliphatic N-carbamoyl hydrazones, providing protected alpha-aryl monoalkylhydrazines with high enantioselectivities. The resulting monosubstituted hydrazines can serve as key building blocks for the synthesis of various organic compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Inorganic & Nuclear
Jessica Margalef, Maria Biosca, Pol de la Cruz Sanchez, Jorge Faiges, Oscar Pamies, Montserrat Dieguez
Summary: The success of phosphine-oxazoline ligands has led to advancements in P-oxazoline ligand families, resulting in diverse structures and more efficient ligands for asymmetric transformations. Through proper design, these heterodonor bidentate ligand families exhibit superior catalytic performance in a variety of asymmetric reactions.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Vasco Corti, Mathias Kirk Thaegersen, Valdemar Juel Enemaerke, Nomaan M. Rezayee, Casper L. Barlose, Karl Anker Jorgensen
Summary: The first atroposelective aminocatalytic methodology for the construction of C-N atropisomers is described. By directly coupling indole-2-carboxaldehydes to ortho-quinones, a new library of functionalized and enantioenriched C-N atropisomers was obtained using a designed and synthesized aminocatalyst. The synthetic utility of these atropisomers was demonstrated through various transformations.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Applied
Irma Garcia-Monzon, Jorge Borges-Gonzalez, Tomas Martin
Summary: The heterogenization of homogeneous catalysts onto a solid support is a crucial step towards sustainable chemistry. In this study, we developed a series of polymer-supported tetrahydropyran-based hybrid dipeptides as active catalysts for the enantioselective Michael addition of aldehydes to beta-nitrostyrenes. The optimal anchor position and orientation between the catalyst and solid support, as well as the linker length, were carefully designed to enhance the catalytic efficiency. These supported catalysts exhibited high yields and enantiomeric excesses, and detailed deactivation studies provided important insights for prolonging their useful life.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Gianluca Casotti, Vincenzo Rositano, Anna Iuliano
Summary: Stabilised arylzinc iodide prepared by direct insertion of zinc into aryl iodides, were successfully applied as nucleophiles in the Hayashi Rh-catalysed enantioselective conjugate addition to enones, with high yields and 99% ee of the addition product. The general applicability of the protocol was confirmed by using different arylzinc iodides and enones, as well as organometallic reagents with both halogen and electrophilic groups.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Yiqi Ren, Maodi Wang, Qihua Yang, Junfa Zhu
Summary: The development of chiral solid catalysts using unconventional strategies is crucial for efficient heterogeneous asymmetric catalysis. The study presents a chiral solid catalyst, chiral diamine modified Ni/SiO2, for asymmetric Michael addition. The experimental results demonstrate that the peripheral Ni sites in close contact with SiO2 support are likely to be the active sites.
Article
Chemistry, Organic
Bin Mao, Zhi-Wei Chen, Jian-Fei Wang, Chao-Huan Zhang, Zhi-Qian Du, Chuan-Ming Yu
Summary: In this study, the enantioselective organocatalytic conjugate alkenylation of fi-substituted alkenyl benzimidazoles was achieved, leading to the formation of beta-stereogenic 2-alkyl benzimidazole derivatives with excellent enantio-selectivities. Chiral binaphthols were found to be effective catalysts for promoting the nucleophilic addition of bench-stable alkenyl trifluoroborate salts under mild conditions. By utilizing C=N-containing azaarenes as activating groups, the applications of these catalysts were expanded. The synthetic utility of this strategy was demonstrated by converting the products into several useful enantiomerically enriched benzimidazole building blocks.
Article
Chemistry, Physical
Fangfang Guo, Jiean Chen, Yong Huang
Summary: Recently, chiral N-heterocyclic carbenes (NHCs) have been established as powerful catalysts for enantioselective bond-forming processes via noncovalent interactions. A bifunctional NHC with an embedded hydrogen-bonding motif has been reported in this study, showing remarkable tolerance of various Michael acceptors in an asymmetric aza-conjugate addition reaction, with catalytic efficiency far exceeding that of the benchmark tertiary amine-thiourea scaffold.
Article
Chemistry, Organic
Ruslan A. Kovalevsky, Maxim Smirnov, Alexander S. Kucherenko, Kseniya A. Bykova, Elizaveta Shikina, Sergei G. Zlotin
Summary: In this study, 2-nitroallylic carbonates were used for the first time as promising biselectrophilic C3 synthons. They reacted with kojic acid derivatives in a bifunctional squaramide catalyzed asymmetric domino reaction, yielding nitro compounds that contain two hydroxypyranone units. The reaction products undergo noncatalytic epimerization at the carbon atom next to the nitro group. A plausible mechanism of the epimerization based on reversible formation of intermediate aci-nitro compound is proposed. The double addition products were transformed into configurationally stable acetates and chiral nitro glutarates, which are promising precursors for chiral amino glutaric acid derivatives.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shibo Yu, Qihang Cai, Tianxu Yu, Jiahui Li, Chao Yao, Yue-Ming Li
Summary: This paper describes the design and application of new chiral ligands based on binaphthyl and proline skeletons, which incorporate regulatable electronic and steric properties for the imidazoline functional groups. These ligands form chiral complexes with different metal salts and can be used as catalysts for enantioselective conjugate addition reactions, resulting in high yields and excellent enantiomeric excess.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Qihua Yang, Junfa Zhu, Yiqi Ren, Maodi Wang
Summary: In this study, a chiral solid catalyst, chiral diamine modified Ni/SiO2, was prepared for asymmetric Michael addition. The experimental results showed that the chiral diamine modified Ni/SiO2 achieved a higher ee value and turnover frequency compared to chiral Ni complexes. The peripheral Ni sites in close contact with SiO2 support were identified as the active sites, distinct from homogeneous complexes. Continuous flow production of chiral compounds for more than 65 hours was achieved using the solid catalysts in a fixed bed reactor.
Article
Chemistry, Organic
Shuting Tan, Jian-Guo Liu, Ming-Hua Xu
Summary: A rhodium-catalyzed asymmetric 1,4-addition reaction provides a practical approach for synthesizing highly enantioenriched chiral N-alkylindoles.
Article
Chemistry, Physical
Ying Wang, JianJun Yin, Yanfei Li, Xiuping Yuan, Tao Xiong, Qian Zhang
Summary: We report the successful copper-catalyzed asymmetric conjugate addition of beta-substituted alkenyl heteroarenes, one of the most challenging Michael acceptors, with alkenes. This method enables the synthesis of diverse chiral heteroarenes with good to excellent yields and excellent enantioselectivity. Moreover, the Michael addition products can be further transformed into valuable acyclic enantioenriched structures through chiral amine catalysis. Mechanistic studies suggest that the hydrocupration step may be the turnover-limiting step, and control experiments provide insights into the preferential alkene hydrocupration in the presence of beta-substituted alkenyl heteroarenes and the Ph-BPE-ligated CuH catalyst.
Article
Chemistry, Multidisciplinary
K. C. Nicolaou, Quan Cai, Bo Qin, Mette T. Petersen, Remi J. T. Mikkelsen, Philipp Heretsch
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Physical
Weilu Wang, Ying Wang, Bin Wu, Rihong Cong, Wenliang Gao, Bo Qin, Tao Yang
CATALYSIS COMMUNICATIONS
(2015)
Article
Chemistry, Multidisciplinary
K. C. Nicolaou, Quan Cai, Hongbao Sun, Bo Qin, Shugao Zhu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Article
Chemistry, Multidisciplinary
Bo Qin, Wei Qiang Ong, Ruijuan Ye, Zhiyun Du, Xiuying Chen, Yan Yan, Kun Zhang, Haibin Su, Huaqiang Zeng
CHEMICAL COMMUNICATIONS
(2011)
Article
Chemistry, Multidisciplinary
Chang Sun, Changliang Ren, Yuchen Wei, Bo Qin, Huaqiang Zeng
CHEMICAL COMMUNICATIONS
(2013)
Article
Chemistry, Multidisciplinary
Haoliang Fu, Hu Chang, Jie Shen, Lin Yu, Bo Qin, Kun Zhang, Huaqiang Zeng
CHEMICAL COMMUNICATIONS
(2014)
Article
Materials Science, Ceramics
Daixiong Zhang, Xueming Li, Bo Qin, Xiaolin Li, Xiaogang Guo, Chuan Lai
JOURNAL OF THE AMERICAN CERAMIC SOCIETY
(2014)
Article
Materials Science, Multidisciplinary
Daixiong Zhang, Xueming Li, Bo Qin, Chuan Lai, Xiaogang Guo
Article
Chemistry, Organic
Zhiyun Du, Bo Qin, Chang Sun, Ying Liu, Xi Zheng, Kun Zhang, Allan H. Conney, Huaqiang Zeng
ORGANIC & BIOMOLECULAR CHEMISTRY
(2012)
Article
Chemistry, Organic
Bo Qin, Chang Sun, Ying Liu, Jie Shen, Ruijuan Ye, Jia Zhu, Xin-Fang Duan, Huaqiang Zeng
Article
Chemistry, Organic
Bo Qin, Liuyin Jiang, Sheng Shen, Chang Sun, Weixing Yuan, Sam F. Y. Li, Huaqiang Zeng
Article
Chemistry, Multidisciplinary
Liu Ying, Qin Bo, Zeng HuaQiang
SCIENCE CHINA-CHEMISTRY
(2012)
Article
Chemistry, Physical
Qiong Wu, Fang Tu, Long Long, Bo Qin
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2019)
Article
Chemistry, Multidisciplinary
Lu Huang, Hongyuan Cheng, Luxi Wang, Xiaojing Wu, Bo Qin
Summary: Driven by pi-pi and CH-pi interactions, Cu(II)-CPCs crystals formed from 1D aggregated copper(II) complexes exhibit distinct fluorescence properties in response to anions, with surface structure being the main factor controlling their fluorescence response as shown by extensive data analysis.
CRYSTAL GROWTH & DESIGN
(2021)
Article
Chemistry, Physical
Yongjie He, Qi Zhang, Hanlin Cheng, Yang Liu, Yue Shu, Yang Geng, Yujie Zheng, Bo Qin, Yongli Zhou, Shanshan Chen, Jing Li, Meng Li, Omololu George Odunmbaku, Chen Li, Tatyana Shumilova, Jianyong Ouyang, Kuan Sun
Summary: This study focuses on the use of mobile ions as charge carriers in i-TE hydrogels and reveals that the influence of ions on hydrogen bonding is a crucial factor in determining thermoelectric performance. Among various i-TE hydrogels, the PVA/CsI hydrogel demonstrates the highest ionic Seebeck coefficient of 52.9 mV K-1, which is the largest among all reported i-TE materials to date.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
