Article
Chemistry, Multidisciplinary
Jinliang Song, Manli Hua, Xin Huang, Aurelia Visa, Tianbin Wu, Honglei Fan, Minqiang Hou, Zhaofu Zhang, Buxing Han
Summary: The study fabricated a novel zirconium organoborate for the selective reduction of biomass-derived carbonyl compounds via MPV reaction. The number of borate groups on the ligands significantly affected the catalytic activity, with the activation role of borate groups on hydroxyl groups being crucial for the hydrogen source. The excellent performance of Zr-BDB was attributed to the synergetic effect of Zr4+ and borate groups, marking the first successful enhancement of Zr-based catalysts in MPV reactions using borate groups.
Article
Chemistry, Multidisciplinary
Christianah Aarinola Akinnawo, Ndzondelelo Bingwa, Reinout Meijboom
Summary: Mesoporous zirconia doped with Cr exhibited outstanding reactivity and 100% selectivity in the Meerwein-Ponndorf-Verley reduction, mainly due to the intrinsic properties of its surface mesostructure rather than specific surface area. The synergistic effect between Cr and Zr species in the binary oxide facilitated the Lewis acidity-induced performance of the Cr_ZrO2 catalyst, showcasing its innovative application in the green synthesis of unsaturated alcohols.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Agricultural Engineering
Jirui Yang, Yanwei Zhang, Feng Shen, Xinhua Qi
Summary: A zirconium-containing mesoporous composite catalyst was developed using a sol-gel process and soft templating method, with glucose and F127 triblock copolymer as the ligand and pore-forming agent. The composite catalyst showed excellent performance in catalyzing the Meerwein-Ponndorf-Verley reduction of furfural, achieving a maximum furfuryl alcohol yield of 93.4% at 180 degrees C within 180 min in 2-propanol. The catalyst also displayed good reusability.
BIOMASS & BIOENERGY
(2023)
Article
Chemistry, Multidisciplinary
H-H Mautschke, F. X. Llabres i Xamena
Summary: Zr-containing MOF-808 is a promising heterogeneous catalyst for the diastereoselective reduction of ketosteroids to hydroxysteroids, achieving the synthesis of elusive 17α-hydroxy derivatives in one step. The process is found to be chemoselective and regioselective, with the entropic term controlling the diastereoselectivity by confining the reaction inside the MOF cavities where Zr4+ active sites are located.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Md Anwar Hossain, Tinnakorn Saelee, Sarttrawut Tulaphol, Mohammad Shahinur Rahaman, Thanh Khoa Phung, Thana Maihom, Piyasan Praserthdam, Supareak Praserthdam, Daniel J. Yelle, Noppadon Sathitsuksanoh
Summary: In this study, efficient hydrogenolysis of lignin was achieved using Ru/C catalyst and internal hydrogen. The aliphatic hydroxyl groups in lignin facilitated the cleavage of beta-O-4 bonds and the formation of phenolic monomers. Solvents with high donor numbers enhanced the yield of phenolic monomers. These findings offer a novel approach for the design of lignin isolation processes and solvent systems in biorefineries.
Review
Chemistry, Physical
Juan Francisco Minambres, Jiri Cejka
Summary: Meerwein-Ponndorf-Verley (MPV) reduction is a selective process that catalyzes the synthesis of alcohols from aldehydes and ketones. Despite extensive research, questions about the catalytic process remain unanswered. This review focuses on recent advances in MPV, including the catalytic materials used and their properties, as well as new applications in biomass transformation and the synthesis of valuable products.
CATALYSIS REVIEWS-SCIENCE AND ENGINEERING
(2023)
Article
Chemistry, Organic
Gaolin Li, Meichen Li, Zhen Xia, Ze Tan, Wei Deng, Chen Fang
Summary: The Meerwein-Ponndorf-Verley (MPV)-type reduction between benzonitriles and benzylic alcohols under transition metal-free conditions has been demonstrated for the first time. The reaction involves hydrogen transfer reduction and subsequent reactions, resulting in the formation of amides. Preliminary mechanistic investigations suggest the involvement of multiple MPV-type hydrogen transfer processes.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Gaolin Li, Meichen Li, Zhen Xia, Ze Tan, Wei Deng, Chen Fang
Summary: This study demonstrates for the first time the feasibility of Meerwein-Ponndorf-Verley (MPV)-type reduction between benzonitriles and benzylic alcohols under transition-metal-free conditions. The reaction can be efficiently carried out using simple KOt-Bu as the base, and the resulting product is an amide incorporating both the alcohols and the nitriles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Mohammad Shahinur Rahaman, Sarttrawut C. Tulaphol, Md. Anwar M. Hossain, Matthew Mulvehill, Joshua Spurgeon, Thana Maihom, Noppadon Sathitsuksanoh
Summary: Liquid phase catalytic hydrogenation is crucial for the production of platform chemicals from biomass-derived carbonyl compounds. In this study, the chemical pathway of transfer hydrogenation of benzaldehyde by Hf- and Zr-containing MOF-808 and UiO-66 catalysts was explored. It was found that MOF-808(Hf) exhibited the highest selectivity with a conversion rate of 99%.
MOLECULAR CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Jinliang Song, Chao Xie, Zhimin Xue, Tiejun Wang
Summary: A Zr-containing montmorillonite catalyst (Zr-MMT) was constructed and found to exhibit high catalytic activity in the reduction of biomass-derived carbonyl compounds. The excellent performance of Zr-MMT can be attributed to the presence of positively charged Zr species and suitable basic sites that facilitate the hydrogen transfer process.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Physical
Qingrui Peng, Haijun Wang, Yongmei Xia
Summary: The utilization of renewable raw materials to synthesize functional solid catalytic materials is an attractive topic. In this study, an amorphous Quercetin-Zr catalyst was synthesized using quercetin and ZrCl4, which exhibited excellent catalytic activity and high yield of furfuryl alcohol.
Article
Chemistry, Physical
Zhuizhui Su, Bingxing Zhang, Xiuyan Cheng, Fanyu Zhang, Qiang Wan, Lifei Liu, Xiuniang Tan, Dongxing Tan, Lirong Zheng, Jianling Zhang
Summary: In this study, ultra-small UiO-66-NH2 nanoparticles with a size of 8-15 nm were successfully synthesized and found to have more unsaturated coordination positions and increased Lewis acidity. Compared to larger particles synthesized using traditional methods, these ultra-small nanoparticles exhibit improved catalytic activity in the Meerwein-Ponndorf-Verley reaction.
GREEN ENERGY & ENVIRONMENT
(2022)
Article
Biochemistry & Molecular Biology
Hans Hilmar Mautschke, Francesc X. Llabres Xamena
Summary: Zr-containing MOF-808 is an excellent heterogeneous catalyst for the diastereoselective Meerwein-Ponndorf-Verley reduction of substituted cyclohexanones. The presence of substituents at specific positions drives the reaction towards the formation of specific isomers, and the porous structure of the MOF allows for selectivity.
Article
Chemistry, Physical
Owain T. Beynon, Alun Owens, Christian Carbogno, Andrew J. Logsdail
Summary: The characterization of zeolitic materials through spectroscopic analysis of vibrations informs about bonding characteristics and adsorbent behavior. Computational simulations often ignore anharmonic effects which significantly impact spectral characteristics. This study demonstrates the impact of anharmonicity on the synthesis of Sn-BEA structures and highlights the importance of incorporating anharmonic effects in vibrational spectrum simulations for accurate characterization and application of zeolitic materials.
JOURNAL OF PHYSICAL CHEMISTRY C
(2023)
Article
Chemistry, Multidisciplinary
Sina Sharifi, Hannah Sharifi, Darrell Koza, Ali Aminkhani
Summary: A catalytic system consisting of AlCl3/Et3N in CH2Cl2 has been developed to selectively convert a wide range of aliphatic and aromatic aldehydes to the corresponding alcohols, acids, and dimerized esters at room temperature with high yields. Higher AlCl3 content favors the Cannizzaro reaction, while lower content favors the Tishchenko reaction. The presence of hydride donor alcohols in the reaction mixture directs the reaction towards the Meerwein-Ponndorf-Verley reaction.
MONATSHEFTE FUR CHEMIE
(2021)
Article
Chemistry, Inorganic & Nuclear
Tomohiro Agou, Daisuke Aso, Shoji Kataoka, Ryota Tuchimochi, Hiroki Fukumoto, Takashi Yamazaki, Tomoko Kawasaki-Takasuka, Yoshiyuki Mizuhata, Norihiro Tokitoh, Toshio Kubota
JOURNAL OF FLUORINE CHEMISTRY
(2018)
Article
Chemistry, Organic
Riku Shinohara, Narihito Ogawa, Hidehisa Kawashima, Kyohei Wada, Shun Saito, Takashi Yamazaki, Yuichi Kobayashi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Inorganic & Nuclear
Shoji Kataoka, Hiroki Fukumoto, Tomoko Kawasaki-Takasuka, Takashi Yamazaki, Katsuyuki Nishimura, Tomohiro Agou, Toshio Kubota
JOURNAL OF FLUORINE CHEMISTRY
(2019)
Article
Chemistry, Inorganic & Nuclear
Kana Mitobe, Tomoko Kawasaki-Takasuka, Tomohiro Agou, Toshio Kubota, Takashi Yamazaki
JOURNAL OF FLUORINE CHEMISTRY
(2019)
Article
Chemistry, Organic
Toshihito Goto, Tomoko Kawasaki-Takasuka, Takashi Yamazaki
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Yuji Tamura, Rina Yada, Tomoko Kawasaki-Takasuka, Tomohiro Agou, Toshio Kubota, Takashi Yamazaki
Article
Polymer Science
Tomohiro Agou, Kazuto Yoshinari, Tomohiro Shirai, Shigeyuki Yamada, Tsutomu Konno, Yoshiyuki Mizuhata, Norihiro Tokitoh, Sana Yasuda, Takashi Yamazaki, Hiroki Fukumoto, Toshio Kubota
Article
Chemistry, Organic
Takashi Yamazaki, Yoh Nakajima, Minato Iida, Tomoko Kawasaki-Takasuka
Summary: The study presents a concise method for preparing 4,4,4-trifluorobut-2-yn-1-ones by oxidizing readily accessible propargylic alcohols, and demonstrates their use as Michael acceptors for constructing aromatic and heteroaromatic compounds.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Takashi Yamazaki, Masahito Taketsugi, Tomoko Kawasaki-Takasuka, Tomohiro Agou, Toshio Kubota
Summary: Using CuBr·SMe2 and TMSCl as catalysts, Michael addition reactions of various Grignard reagents to 4,4,4-trifluorinated alpha, beta-unsaturated carboxylic acid derivatives with 4-substituted oxazolidin-2-ones as a chiral auxiliary proceed smoothly to construct the desired products with quaternary stereocenters possessing a CF3 group in good to excellent yields.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2021)
Article
Biochemistry & Molecular Biology
Yoko Hamada, Rio Matsunaga, Tomoko Kawasaki-Takasuka, Takashi Yamazaki
Summary: The CF3 group was found to significantly influence the base-mediated proton shift in propargylic or allylic alcohols with high CF3 content, allowing for the synthesis of alpha, beta-unsaturated or saturated ketones. This method was applied to the synthesis of allyl vinyl ethers in this study, achieving the desired rearrangement through proton shift.
Article
Chemistry, Organic
Kyu Terashima, Tomoko Kawasaki-Takasuka, Ichiro Minami, Takashi Yamazaki
Summary: A convenient method for synthesizing (hydroxyphenyl)perfluoro-alkylmethanols was developed by utilizing the Meerwein-Ponndorf-Verley (MPV) type reduction. The key step involved the in situ generation of perfluoroalkylated ketones. The resulting alcohols underwent successful transformation of the benzylic OH group to H or Rf(CH2)(n)O via the corresponding chlorides, a conversion not easily achieved by other methods.
Article
Chemistry, Inorganic & Nuclear
Takashi Yamazaki, Minato Iida, Tomoko Kawasaki-Takasuka, Tomohiro Agou
Summary: The utilization of 3,3,3-trifluoroprop-1-yne in the presence of BF3·OEt2 was demonstrated to achieve regio- and stereoselective ring opening of various epoxides, leading to the synthesis of CF3-containing homopropargylic alcohols in high yields.
JOURNAL OF FLUORINE CHEMISTRY
(2022)
Article
Chemistry, Organic
Kyu Terashima, Tomoko Kawasaki-Takasuka, Takashi Yamazaki
Summary: The 1,6-conjugate additions of in situ generated delta-CF3-delta-substituted p-quinone methides with various heteronucleophiles under mild conditions successfully led to the construction of fully substituted carbon centers, including a heteroatom and a CF3 group. It was also discovered that some amines can efficiently cleave the TBS protective group, and the addition of a catalytic amount of an appropriate Bronsted acid can enhance the progress of the desired process.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Kyu Terashima, Tomoko Kawasaki-Takasuka, Tomohiro Agou, Toshio Kubota, Takashi Yamazaki
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Kyu Terashima, Tomoko Kawasaki-Takasuka, Tomohiro Agou, Toshio Kubota, Takashi Yamazaki
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
