Article
Chemistry, Multidisciplinary
Toshimichi Ohmura, Yuta Takaoka, Michinori Suginome
Summary: The copper-catalyzed silafunctionalization of alkynes using silylboronic ester as a silicon source has made rapid progress. The trans-selective 1,2-addition of silylboronic esters to internal arylalkynes was efficiently promoted by the CuOt-Bu/RCy2P/NaOt-Bu catalysts, with a stereochemical switch to cis-addition observed in reactions utilizing Me-2(i-PrO)Si-B(pin) in hydrocarbon solvents including cyclohexane.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Bin-Bin Zhu, Wen-Bo Ye, Zhi-Tao He, Shu-Sheng Zhang, Chen-Guo Feng, Guo-Qiang Lin
Summary: In this study, a regioselective three-component tandem alkylation/coupling reaction was developed for a variety of ortho-iodophenylethylenes. Electron-rich 2-pyridone ligands enabled the formation of aryl-alkenyl-palladacycle intermediates, with discrimination between the two C-Pd bonds based on their steric and electronic properties. Good linear free-energy relationships between regio-/chemoselectivities and Hammett sigma values were observed.
Article
Chemistry, Multidisciplinary
Shay Laps, Fatima Atamleh, Guy Kamnesky, Shaked Uzi, Michael M. Meijler, Ashraf Brik
Summary: This study presents a new approach for synthesizing disulfide-rich bioactive molecules, addressing previous challenges in preparation. Experimental results demonstrate the essential role of the order of disulfide bond formation in proteins with knotted structures. This methodology was utilized to synthesize novel analogues of plectasin with enhanced efficacy against MRSA.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
T. Parker Maloney, Alexander F. Dohoda, Alec C. Zhu, Forrest E. Michael
Summary: In this study, we reported a convenient and transition metal-free intermolecular propargylic C-H amination of alkynes. The reaction showed high yields for terminal, silyl, and internal alkynes with a wide range of functional groups. The regioselectivity of amination was found to be influenced by substitution pattern and relatively remote heteroatomic substituents.
Article
Chemistry, Organic
Raziullah, Mohit Kumar, Afsar Ali Khan, Himangsu Sekhar Dutta, Ashfaq Ahmad, Jayanti Vaishnav, Ruchir Kant, Ravi Sankar Ampapathi, Dipankar Koley
Summary: A regioselective hydroarylative coupling of indolines with internal alkynes has been developed using a Ru(II)-catalyst, providing high yields and easy operation. The method can be applied to a variety of alkyne-containing compounds, showing great potential for broad applications.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jyoti M. Honnanayakanavar, Jagadeesh Babu Nanubolu, Surisetti Suresh
Summary: This study presents a novel copper-catalyzed tandem reaction for the efficient synthesis of a specific three-ring compound, which has been successfully applied to the total synthesis of the anticancer drug TIC10/ONC201.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiao Yu, Wenjing Zhu, Hongyan Liu, Yi Liu, Hongshuang Li, Junfen Han, Guiyun Duan, Zhushuang Bai, Pengfei Zhang, Chengcai Xia
Summary: A novel route involving metal-promoted tandem nitration and halogenation has been developed for the synthesis of N-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives. The method shows high practicality, chemoselectivity, and compatibility with various functional groups. In addition, it uses insensitive and inexpensive nitration reagents and provides a direct approach for the preparation of 4-halo-2-nitroaniline, a crucial intermediate for the synthesis of benzimidazoles and quinoxaline derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Optics
Param Jeet Singh, A. K. Das, Kiran Kumar Gorai, A. Shastri, K. Sunanda, D. Udupa, B. N. Rajasekhar
Summary: Spectroscopic investigations on N,N-dimethylacetamide (DMA) in the vacuum ultraviolet (VUV) and infrared (IR) regions are conducted. The VUV photoabsorption spectrum and IR spectrum of DMA are measured and analyzed with the support of quantum chemical computations. The study reveals the assignments of vibrational bands in the IR spectrum and the contribution of Rydberg states in the dissociation dynamics of DMA upon photoexcitation in the VUV region.
JOURNAL OF QUANTITATIVE SPECTROSCOPY & RADIATIVE TRANSFER
(2022)
Article
Nanoscience & Nanotechnology
Shigang Chen, Pan Sun, John Humphreys, Peimiao Zou, Mengfei Zhang, Georgina Jeerh, Boyao Sun, Shanwen Tao
Summary: The use of a hybrid electrolyte of DMA and concentrated nitrate has shown potential in providing good electrochemical stability while using fewer dissolved salts. Through analysis and molecular dynamics simulation, it was found that the stability of the electrolyte can be attributed to the weakened Li+/Zn2+ solvation sheath caused by the low permittivity of DMA. This work demonstrates the feasibility of utilizing a relatively dilute electrolyte dissolved in oxygen for a highly stable aqueous rechargeable battery.
ACS APPLIED MATERIALS & INTERFACES
(2021)
Article
Chemistry, Organic
Vijay Babu Pathi, Arindam Manna, Ravuri Srinath, Supriyo Adhikary, Biswadip Banerji
Summary: A regioselective synthesis of N-fused benzimidazo-indolo-isoquinoline heterocycles was achieved via a Pd-catalyzed domino coupling reaction. This method provided a direct and facile route to access structurally complex polyheterocycles in moderate to good yields. The resulting hybrid molecules showed structural similarity with naturally isolated alkaloids and exhibited strong fluorescence in both solid and solution phases.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Sushma Naharwal, Narendra Dinkar Kharat, Chikkagundagal K. Mahesha, Kiran Bajaj, Rajeev Sakhuja
Summary: Regioselective C-arylation and C,N-diarylation of 2-aryl-2,3-dihydrophthalazine-1,4-diones have been achieved successfully using diaryliodonium salts under base-mediated slightly modified Pd catalyzed conditions. These ligand-driven transformations afforded a wide range of diversely decorated bi(hetero)aryls in good-to-excellent yields, while N-arylated product can be obtained under similar Pd-catalyzed conditions in the absence of a ligand.
SYNTHESIS-STUTTGART
(2023)
Article
Polymer Science
Shunya Inukai, Naruki Kurokawa, Fuyuaki Endo, Tomoki Maeda, Atsushi Hotta
Summary: Mechanically tough PLLA/DMAc gels were synthesized by rapid quenching using liquid nitrogen. The gels formed by liquid nitrogen quenching exhibited higher storage modulus and more uniform network structure compared to those formed by room temperature cooling.
Article
Chemistry, Multidisciplinary
Fangfang Wu, Yuchao Chen, Yulong Chen, Ruilian Yin, Yancong Feng, Dong Zheng, Xilian Xu, Wenhui Shi, Wenxian Liu, Xiehong Cao
Summary: Optimization of electrolyte composition is a practical way to improve the performance of aqueous zinc-ion batteries (ZIBs). In this study, a mixture electrolyte containing 10 vol% of N,N-Dimethylacetamide (DMA) and ZnSO4 was used to enhance the reversibility of Zn plating/stripping. It was found that DMA has the ability to reconstruct the solvation structure of Zn2+ and inhibit dendrite growth on Zn anode.
Article
Chemistry, Organic
Nalladhambi Neerathilingam, Mandapati Bhargava Reddy, Ramasamy Anandhan
Summary: This study reports a visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N, N-dibenzylanilines to 2 degrees amides. Furthermore, the protocol has been applied to the synthesis of quinazolinones from 2-(dibenzylamino)benzamide. Mechanistic studies suggest that the reaction may involve the in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yan-Dong Zhang, Xiao-Yu Li, Qian-Kun Mo, Wen-Bin Shi, Jia-Bao Zhao, Shou-Fei Zhu
Summary: In this study, we developed new Co complexes with cyclopropane-based diphosphine ligands that can catalyze highly chemo-, regio-, and stereoselective hydroboration reactions of unsymmetrical internal alkynes. These reactions exhibit unusual regioselectivity, leading to the synthesis of trisubstituted alkenylborates and alkenes with different stereochemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Sho Yamaguchi, Hiroki Kondo, Kohei Uesugi, Katsumasa Sakoda, Koichiro Jitsukawa, Takato Mitsudome, Tomoo Mizugaki
Summary: The study established a highly efficient catalytic system for converting biomass-derived alcohols into hydrocarbon fuels without the need for hydrogen gas. By using Pd/CeO2 catalyst, a wide range of alcohols were successfully converted into shorter carbon chain hydrocarbons with high yields. The catalyst was easily recoverable and reusable, making it a simple and sustainable method for producing hydrocarbon fuels from biomass-derived oxygenates.
Article
Chemistry, Multidisciplinary
Shu Fujita, Sho Yamaguchi, Jun Yamasaki, Kiyotaka Nakajima, Seiji Yamazoe, Tomoo Mizugaki, Takato Mitsudome
Summary: Alloying non-noble metal nanoparticles with phosphorus is a promising strategy for developing smart catalysts with high activity and air stability. For example, the novel nano-Ni2P catalyst exhibits excellent hydrogenation performance in water and can be easily reused without pretreatment.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Hiroya Ishikawa, Min Sheng, Ayako Nakata, Kiyotaka Nakajima, Seiji Yamazoe, Jun Yamasaki, Sho Yamaguchi, Tomoo Mizugaki, Takato Mitsudome
Summary: In this study, a supported cobalt phosphide nanoalloy catalyst was developed for the selective hydrogenation of furfural derivatives, showing high efficiency and air stability without the need for H-2 pretreatment. Backdonation from Co d-electrons to the pi* orbital of furfural derivatives was found to play a key role in the highly efficient hydrogenation process.
Article
Chemistry, Multidisciplinary
Sho Yamaguchi, Shu Fujita, Kiyotaka Nakajima, Seiji Yamazoe, Jun Yamasaki, Tomoo Mizugaki, Takato Mitsudome
Summary: A nickel phosphide nanoalloy supported by hydrotalcite demonstrated high catalytic activity for the hydrogenation of maltose, leading to efficient production of maltitol. Cooperative catalysis by the nanoalloy and the support played a key role in this process, enabling high-yield production even at ambient temperature. The catalyst showed promising performance in concentrated maltose solutions, highlighting its potential for sustainable production of maltitol.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Inorganic & Nuclear
Sho Yamaguchi, Tomoo Mizugaki, Takato Mitsudome
Summary: The highly efficient and selective hydrogenation of D-xylose to D-xylitol was achieved using a hydrotalcite-supported nickel phosphide nanoparticle catalyst. Notably, the reaction proceeded even under 1 bar of H-2 or at room temperature for the first time. The catalyst exhibited the highest activity among previously reported non-noble metal catalysts, with potential for industrial production of D-xylitol.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Min Sheng, Sho Yamaguchi, Ayako Nakata, Seiji Yamazoe, Kiyotaka Nakajima, Jun Yamasaki, Tomoo Mizugaki, Takato Mitsudome
Summary: An air-stable, active, and reusable non-noble-metal-based heterogeneous catalyst, hydrotalcite-supported cobalt phosphide nanorods (Co2P NR/HT), has been developed for the selective hydrogenation of nitriles to primary amines. The catalyst shows broad substrate generality and high activity under mild conditions, enabling nitrile hydrogenation with high yields without the need for ammonia.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Organic
Hang Xu, Sho Yamaguchi, Takato Mitsudome, Tomoo Mizugaki
Summary: In this study, the catalytic oxidative trimerization and oxygenative cleavage reactions of indoles were achieved using a copper nitride nanocube catalyst, producing valuable nitrogen-containing compounds such as indolin-3-ones and 2-ketoanilides under additive-free conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hang Xu, Sho Yamaguchi, Takato Mitsudome, Tomoo Mizugaki
Summary: A simple and efficient hydroboration of alkynes using Cu3N NC catalyst has been reported for the first time. The catalyst allows the synthesis of vinyl boronate esters under mild reaction conditions without the need for additives or elevated temperatures. The Cu3N NCs can also be easily separated and reused, offering an environmentally friendly route for the production of vinyl boronates.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Physical
Hiroya Ishikawa, Naoki Nakatani, Sho Yamaguchi, Tomoo Mizugaki, Takato Mitsudome
Summary: We report the use of ruthenium phosphide nanoparticles (Ru2P/SiO2) as a highly active and robust catalyst for the hydrogenation of sulfur-containing nitroarenes, with activity 34 times higher than that obtained with Ru nanoparticles. Various sulfur-containing nitroarenes were hydrogenated under 1 bar of H2, resulting in high yields of anilines, including important pharmaceutical intermediates. The electronic and geometrical effects of P surrounding Ru species in Ru2P/SiO2 were found to be crucial for enhancing the catalyst's activity and durability against sulfur poisoning.
Article
Multidisciplinary Sciences
Tomohiro Tsuda, Min Sheng, Hiroya Ishikawa, Seiji Yamazoe, Jun Yamasaki, Motoaki Hirayama, Sho Yamaguchi, Tomoo Mizugaki, Takato Mitsudome
Summary: Iron-based catalysts are advantageous metal catalysts due to their abundance and low toxicity. However, conventional iron nanoparticle catalysts have low activity in liquid-phase reactions and lack air stability. In this study, air-stable iron phosphide nanocrystal catalysts were developed to overcome the trade-off between activity and stability. These catalysts exhibited high activity for liquid-phase nitrile hydrogenation and can be immobilized on suitable supports for improved performance.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Physical
Hiroya Ishikawa, Naoki Nakatani, Sho Yamaguchi, Tomoo Mizugaki, Takato Mitsudome
Summary: We report the use of ruthenium phosphide nanoparticles (Ru2P/SiO2) as a highly active and robust catalyst for the hydrogenation of sulfur-containing nitroarenes, showing 34 times higher activity than Ru nanoparticles. Various sulfur-containing nitroarenes were successfully hydrogenated under 1 bar of H2, leading to high yields of aniline products, including valuable pharmaceutical intermediates. The study highlights the importance of the electronic and geometrical effects of P surrounding Ru species in Ru2P/SiO2 for enhanced activity and durability against sulfur poisoning.
Article
Chemistry, Physical
Saburo Hosokawa, Noriyuki Fukuzumi, Tetsu Nakatani, Tetsuo Honma, Tomoo Mizugaki, Tsunehiro Tanaka, Kenji Wada
Summary: The study demonstrates the selective synthesis of acetaldehyde by hydrogenation of acetic acid catalyzed by Pd-Fe alloy nanoparticles derived from Pd/Fe2O3. The optimal Pd loading amount (28-44 wt%) prevents the formation of iron carbides and leads to excellent acetaldehyde yield. In situ XAFS measurements show the reductive pretreatment of Pd/Fe2O3 forms core-shell type Pd-Fe alloy nanoparticles.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Katsumasa Sakoda, Sho Yamaguchi, Takato Mitsudome, Tomoo Mizugaki
Summary: A heterogeneous catalytic system Pt-Mo/ZrO2 was developed for the selective hydrodeoxygenation (HDO) of esters to synthesize unsymmetrical ethers. Under mild reaction conditions, a wide range of esters could be transformed into the corresponding unsymmetrical ethers. The Pt-Mo/ZrO2 catalyst also demonstrated successful conversion of a biomass-derived triglyceride into the corresponding triether. The cooperative catalysis between Pt nanoparticles and neighboring molybdenum oxide species on the ZrO2 surface played a key role in the highly selective HDO of esters. This catalyst system offers an efficient strategy for synthesizing unsymmetrical ethers and expands the scope of sustainable reaction processes.
Article
Chemistry, Multidisciplinary
Hiroya Ishikawa, Sho Yamaguchi, Ayako Nakata, Kiyotaka Nakajima, Seiji Yamazoe, Jun Yamasaki, Tomoo Mizugaki, Takato Mitsudome
Summary: This study demonstrates that phosphorus alloying significantly increases the deoxygenation activity of precious metal nanoparticles for sulfoxide conversion, and provides an efficient method to improve metal nanoparticle catalysis for diverse organic synthesis.
Article
Chemistry, Multidisciplinary
Sho Yamaguchi, Shu Fujita, Kiyotaka Nakajima, Seiji Yamazoe, Jun Yamasaki, Tomoo Mizugaki, Takato Mitsudome
Summary: The study presents a non-noble metal catalyst, nickel phosphide nanoparticle supported on hydrotalcite, which effectively catalyzes the selective hydrogenation of d-glucose to d-sorbitol in water, with high yield and over 99% selectivity under mild conditions. This nano-Ni2P/HT catalyst shows superior activity compared to other non-noble metal catalysts, can operate at ambient temperature under just 1 bar of H-2, and is stable and reusable, providing a cheap, green, and sustainable route for the production of d-sorbitol.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)