Article
Chemistry, Organic
Ryudai Michikita, Yoshinosuke Usuki, Tetsuya Satoh
Summary: A Rh(III)-catalyzed double C-H annulation of 3-(acetylamino)coumarins with internal arylacetylenes is reported, which selectively produces 8-aryl-6H- chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-ones accompanied by the formation of two C-C and two C-N bonds. This method also provides a straightforward route to natural product inspired pentacyclic pyrrolocoumarin derivatives from readily available building blocks.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Vladimir B. Kharitonov, Dmitry V. Muratov, Yulia V. Nelyubina, Dmitry A. Loginov
Summary: This study demonstrated the influence of catalyst and alkyne nature on the regioselectivity of rhodium-catalyzed annulation of alkoxy-substituted benzoic acids. X-ray diffraction and DFT calculation data showed that the regioselectivity was determined by both steric and coordination effects of methoxy groups. The findings are believed to be applicable to other C-H activation reactions of methoxy-substituted arene compounds.
Article
Chemistry, Multidisciplinary
Marc Strohmann, Andreas J. Vorholt, Walter Leitner
Summary: This study presents a method for transforming olefins into branched amines by combining hydroformylation/aldol condensation tandem reaction with reductive amination. The method utilizes a combined multiphase system that can be recycled 9 times. The study demonstrates the feasibility of the method and its potential applications in the production of surfactants.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Shusuke Ochi, Zining Zhang, Ying Xia, Guangbin Dong
Summary: In this study, a unique one-carbon ring-expansion strategy was developed to synthesize multi-substituted 2-indanones from benzocyclobutenones and styrene-type olefins. The use of a cationic ligandless rhodium catalyst enabled high reactivity and selectivity towards the (4+1) product. The method exhibited broad functional group tolerance and scalability.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Fatemeh Ghahramani, Malte Meyer, Shreya Unone, Daniel Janssen-Mueller
Summary: A palladium-catalyzed method for the efficient C-C bond activation of HMF derivatives, enabling their arylation with iodobenzenes, has been developed. Mechanistic studies suggest a decarboxylative mechanism. This strategy offers an efficient and sustainable approach for the synthesis of arylfuran derivatives.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Yoshimi Kato, Luqing Lin, Masahiro Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga
Summary: By introducing pseudo-C2 symmetric tunable chiral carboxylic acids, the study achieved enantioselective C(sp(3))-H amidation reactions of substrates such as 2-alkylpyridines, improving the chiral selectivity towards the substrates.
Article
Chemistry, Multidisciplinary
Vladimir B. Kharitonov, Sofiya A. Runikhina, Yulia Nelyubina, Dmitry Muratov, Denis Chusov, Dmitry A. Loginov
Summary: A simple approach was developed to new effective rhodium catalysts for the construction of C-C and C-N bonds based on the 1,2,3,4-tetrahydrofluorenyl ligand. These catalysts showed efficient catalytic activity in various reactions, such as oxidative coupling of benzoic acids with alkynes and reductive amination of aldehydes and ketones, yielding high yields of the desired products.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Roushan Prakash Singh, Soumen Sinhababu, Neal P. Mankad
Summary: This Perspective reviews recent advances and applications of Al/M heterobimetallic catalysis in various areas, including polymerization, epoxide activation and carbonylation. The mechanistic role of the aluminum site is highlighted, and a comprehensive perspective is constructed by including a broad range of Al-containing metalloligands and Al/M combinations.
Article
Chemistry, Multidisciplinary
Linxi Yao, Alemayehu Gashaw Woldegiorgis, Shaoying Huang, Yongtao Wang, Xufeng Lin
Summary: We report a highly enantioselective desymmetrization reaction for the synthesis of axially chiral biaryl N-oxides by atroposelective C-H iodination using a chiral catalyst coordinated by N-benzoyl-l-phenylalanine. A broad range of products were obtained in high yields (up to 99%) with excellent enantioselectivities (up to 98% ee). The products could be synthesized in gram scale, and one of them was shown to be a powerful organocatalyst in asymmetric allylation reaction. Mechanistic evidence and DFT calculations provide insights into the factors leading to high reactivity and excellent enantiocontrol in this reaction.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Wen-Wen Zhang, Qiang Wang, Su-Zhen Zhang, Chao Zheng, Shu-Li You
Summary: Satoh-Miura reaction is an important method for extending pi-systems via C-H activation and alkynyl annulation. However, achieving high enantioselectivity remains challenging. In this study, an asymmetric Satoh-Miura reaction using a SCpRh-catalyst is reported, and it is found that choosing the counteranion of the catalyst is crucial for the desired reactivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Mikhail A. Arsenov, Yury V. Fedorov, Dmitry V. Muratov, Yulia V. Nelyubina, Dmitry A. Loginov
Summary: Efficient conditions for the catalytic oxidative coupling of electron-poor carboxylic acids with diphenylacetylene using rhodium have been optimized, leading to the formation of isocoumarins and polycyclic aromatic hydrocarbons. The photophysical properties of the products in solutions have been studied, showing interesting fluorescence emission and solvatochromic effects.
Review
Chemistry, Organic
Valentin J. Geiger, Regina M. Oechsner, Paul H. Gehrtz, Ivana Fleischer
Summary: This review provides a summary of the recent methods for the synthesis of thioethers using homogeneous metals as catalysts. Due to the widespread presence of the thioether moiety in pharmaceutical, agricultural, and material applications, it is essential to develop new, efficient synthesis methods. Recent efforts have focused on the use of non-precious metal catalysts and the development of new bond-forming processes.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Applied
Jan-Hendrik Schobel, Philipp Elbers, Khai-Nghi Truong, Kari Rissanen, Carsten Bolm
Summary: Two different protocols were presented for the preparation of three-dimensional aza-analogues of 1,2-benzothiazine 1,1-dioxides from sulfonimidamides. The first method involves a rhodium-catalyzed annulation reaction to produce 4-unsubstituted benzothiazine derivatives, while the second method utilizes an iridium catalyst under solvent-free mechanochemical conditions to obtain products with 3,4-disubstituted thiazine rings.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Samuel Hruby, Jan Ulc, Ivana Cisarova, Martin Kotora
Summary: The scope of Rh-catalyzed C-C bond cleavage/annulation of biphenylene with various aromatic nitriles was investigated. Further Rh- and Ir-catalyzed C-H bond activation/annulation sequence of the resulting 9-arylphenanthridines with alkynes led to the formation of cationic [4], [5], [6] helical quinolizinium salts. The helical arrangement of these compounds was confirmed by single-crystal X-ray analysis. Most of the prepared quinolizinium salts exhibited fluorescence emission with a maximum wavelength in the range of 525-623 nm and absolute quantum yields up to 25%.
Article
Chemistry, Multidisciplinary
Tomoki Yoshida, Masaya Ohta, Tomoya Emmei, Takuya Kodama, Mamoru Tobisu
Summary: The C-F bond of acyl fluorides can be cleaved and added across tethered alkenes using a cationic rhodium(I) tetrafluoroborate catalyst. This 1,2-carbofluorination reaction provides a highly efficient method for the synthesis of tertiary alkyl fluoride derivatives with a 100% atom economy. Mechanistic studies demonstrate that the concerted action of a rhodium cation and a tetrafluoroborate anion is crucial for the controlled cleavage and formation of C-F bonds in this catalytic process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Ke-Han He, Wei-Dong Zhang, Ming-Yu Yang, Kai-Li Tang, Mengnan Qu, You-Song Ding, Yang Li
Article
Chemistry, Organic
Wan-Fa Tian, Dang-Po Wang, Shao-Feng Wang, Ke-Han He, Xiao-Ping Cao, Yang Li
Article
Chemistry, Physical
Fang-Fang Tan, Kai-Li Tang, Ping Zhang, Yan-Jun Guo, Mengnan Qu, Yang Li
Article
Chemistry, Organic
Wan-Fa Tian, Chun-Hong Hu, Ke-Han He, Xiao-Ya He, Yang Li
Article
Chemistry, Multidisciplinary
Yang Li
Article
Multidisciplinary Sciences
Fang-Fang Tan, Xiao-Ya He, Wan-Fa Tian, Yang Li
NATURE COMMUNICATIONS
(2020)
Article
Chemistry, Physical
Chao-Zheng Zhou, Yu-Rou Zhao, Fang-Fang Tan, Yan-Jun Guo, Yang Li
Summary: Utilizing renewable formic acid from lignocellulosic biomass as a hydrogen and carbon source, selective hydrogenation and N-methylation of various quinolines, indoles, and anilines were achieved under mild conditions with high efficiencies. Mechanistic studies revealed that the hydrogenation proceeds through a transfer hydrogenation pathway.
Article
Chemistry, Multidisciplinary
Yuan-Li Sun, Fang-Fang Tan, Rong-Gui Hu, Chun-Hong Hu, Yang Li
Summary: We have developed an efficient photocatalytic reaction for the production of alkanes and deuterated alkanes, which is facilitated by the synergistic effect between the appropriate photocatalyst and hydrogen atom transfer catalyst.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Chun-Hong Hu, Yang Li
Summary: A metal-free synthesis of C1-deuterated aldehydes was developed, which utilizes D2O and alpha-oxo carboxylic acids at ambient temperature. This method avoids the use of stoichiometric reductants and oxidants, and can tolerate various functional groups, resulting in high yields and high deuteration levels.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Wen-Min Zhang, Kai-Wen Feng, Rong-Gui Hu, Yan-Jun Guo, Yang Li
Summary: This article presents the development of a visible-light-induced iron catalyst that can selectively transform biomass into formic acid with a high yield of up to 91% at ambient temperature. The mechanism involves multiple iron-catalyzed reactions, and the selectivity is influenced by various factors.
Article
Chemistry, Multidisciplinary
Yan-Jun Guo, Shi-Jun Li, Yuan-Li Sun, Lei Wang, Wen-Min Zhang, Ping Zhang, Yu Lan, Yang Li
Summary: Formic acid is commonly used in chemical processes and as a candidate for hydrogen storage. However, its industrial production relies on fossil resources, making practical production from renewable resources rare. A study demonstrated a method using DMSO to selectively hydrolyze lignocellulosic biomass, achieving high efficiencies in producing formic acid.
Article
Chemistry, Multidisciplinary
Chao-Zheng Zhou, Yu-Rou Zhao, Yan-Jun Guo, Ping Zhang, Yang Li
Summary: This study presents a sustainable method for the production of formaldehyde through the disproportionation of formic acid, catalyzed by iridium-triggered vanadium complexes under mild conditions. The successful demonstration of gram-scale application of in situ generated formaldehyde highlights the potential of this method in industrial production processes.
Article
Chemistry, Physical
Ping Zhang, Yan-Jun Guo, Jianbin Chen, Yu-Rou Zhao, Jun Chang, Henrik Junge, Matthias Beller, Yang Li
Article
Chemistry, Multidisciplinary
Shao-Feng Wang, Xiao-Ping Cao, Yang Li
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
Ke-Han He, Fang-Fang Tan, Chao-Zheng Zhou, Gui-Jiang Zhou, Xiao-Long Yang, Yang Li
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
