Article
Chemistry, Applied
Sara Payamifar, Foad Kazemi, Babak Kaboudin
Summary: This study introduced a convenient nickel-catalyzed protocol for the Suzuki-Miyaura coupling reaction using a simple mixture of Ni(II) and unfunctionalized beta-cyclodextrin in water. The environmentally friendly and cost-efficient method allows the synthesis of biaryls from arylboronic acids and various aryl halides. The catalyst can be recycled for multiple runs with only a small decrease in catalytic activity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Sheng-Qi Qiu, Yu Chen, Xiang-Jun Peng, Shi-Jiang He, Jun Kee Cheng, Yong-Bin Wang, Shao-Hua Xiang, Jun Song, Peiyuan Yu, Junmin Zhang, Bin Tan
Summary: In this study, we achieved the arene-alkene Suzuki-Miyaura coupling reaction between hindered aryl halides and vinyl boronates by designing appropriate ligands and reaction parameters. The axially chiral acyclic aryl-alkenes obtained exhibited remarkable efficiency, enantioselectivity, and E/Z selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Wen-Xin Li, Bo-Wen Yang, Xuan Ying, Zhuo-Wen Zhang, Xue-Qiang Chu, Xiaocong Zhou, Mengtao Ma, Zhi-Liang Shen
Summary: The direct cross-coupling of diaryl sulfoxides with aryl bromides via C-S bond cleavage was achieved using nickel(II) as the catalyst, 1,2-bis(diphenylphosphino)ethane (dppe) as the ligand, and magnesium turnings as the reducing metal in THF. This reaction showed a wide range of substrates and could be used for gram-scale synthesis. The one-pot reaction is operationally simple and economically efficient.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yan-Long Zheng, Pei-Pei Xie, Omid Daneshfar, Kendall N. Houk, Xin Hong, Stephen G. Newman
Summary: A new method has been developed to convert alkyl esters into alkyl ketones, resulting in the synthesis of 65 different alkyl ketones with various functional groups and heterocyclic structures. The study found that catalyst-controlled chemoselectivity could activate the C(acyl)-O bond in the substrate, while density functional theory calculations supported the mechanism of the nickel catalytic cycle.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Editorial Material
Chemistry, Multidisciplinary
Javier F. Reynes, Felipe Garcia
Summary: Several mechanochemically heated processes have been published, but precise control over mechanochemical catalysed coupling reactions has been difficult. A recent report demonstrates a programmable jar heater manifold that efficiently enables the Suzuki-Miyaura-type cross coupling reaction of aryl sulfamates and aryl boronic acid species. This methodology can be easily upscaled 200-fold using twin-screw extrusion methodologies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Gulsah Turkmen
Summary: Novel luminescent 4-phenyl 1,8 naphthalimide derivatives with a color range from cream to green were reported. These dyes were synthesized via Suzuki-Miyaura cross-coupling reactions with a high yield of up to 99%. The photophysical properties and antimicrobial activities of these dyes were investigated.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Organic
Jihye Kim, Jieun Jang, Yoonho Lee, Kwangmin Shin
Summary: In this study, a nickel hydride-catalyzed hydroacylation of aryl alkenes using aroyl fluorides was reported. The reaction proceeds without the need for an exogenous ligand, and the synthetic utility of the method was demonstrated.
Article
Chemistry, Physical
Zeinab Ahmadvand, Mehdi Bayat
Summary: This research aims to establish a more suitable reaction pathway and cross-coupling mechanism for the formation of certain derivatives of quinoxaline and benzofuran by comparing the mechanisms of Suzuki-Miyaura and Hiyama cross-coupling reactions. The findings suggest that the Pd-NHC type complex approach is more desirable for the development of regioselective compounds in competition between different types of cross-coupling reactions.
JOURNAL OF MOLECULAR LIQUIDS
(2021)
Article
Chemistry, Multidisciplinary
Julius Hoepfner, Marius Brehm, Pavel A. Levkin
Summary: The rising costs of pharmaceutical research are currently limiting the productivity of drug discovery and development, but can potentially be reduced through miniaturization of compound synthesis and screening. In this study, the influential palladium-catalyzed Suzuki-Miyaura reaction is successfully implemented at the nanoliter scale on droplet microarrays for the synthesis of an 800-compound library of biphenyls. The synthesis of these compounds requires minimal reagents and solvent volume, and the obtained compounds can be purified and cleaved from excess reactants and catalyst. This novel approach expands the capabilities of droplet microarrays for miniaturized high-throughput chemical synthesis and opens up possibilities for future synthesis and screening of chemical compounds in a single platform.
Article
Chemistry, Multidisciplinary
Takeshi Fujita, Yutaro Kobayashi, Ikko Takahashi, Ryutaro Morioka, Tomohiro Ichitsuka, Junji Ichikawa
Summary: Nickel-catalyzed reductive cross-coupling of allylic difluorides with aryl iodides was successfully achieved, leading to the synthesis of a series of gamma-arylated monofluoroalkenes with moderate to high yields and high Z-selectivities. Mechanistic studies indicated that the cleavage of C-I bonds in aryl iodides and C-F bonds in allylic difluorides occurred through oxidative addition and beta-fluorine elimination, respectively.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Tamae Seo, Koji Kubota, Hajime Ito
Summary: Mechanochemical synthesis using transition-metal catalysts has advantages such as low solvent waste and short reaction times. However, the direct use of transition-metal catalysts in mechanochemical reactions without modifications limits the development of efficient cross-coupling processes. This study presents a new approach, using mechanochemistry-directed design to develop ligands for Suzuki-Miyaura cross-coupling reactions. The embedding of the ligand into a poly(ethylene glycol) polymer prevents catalyst deactivation and shows high catalytic activity at room temperature.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Physical
Alexander F. Schmidt, Anna A. Kurokhtina, Elizaveta Larina, Nadezhda A. Lagoda
Summary: Despite extensive studies on the reaction of Pd intermediates in the Suzuki-Miyaura reaction (SMR), direct evidence supporting the widely accepted assumptions regarding the activity of Pd hydroxo complexes is lacking. This study presents results on the reactivity of Pd-OH and/or Pd-OR-containing complexes in the transmetalation step under ligand-free turnover conditions. The catalytic involvement of specific Pd species was determined under real catalytic conditions by measuring the selectivity of competing reactions.
MOLECULAR CATALYSIS
(2023)
Article
Chemistry, Organic
Xu Zhang, Zhen-Yu Wang, Xing Wang, Hui Xu, Hui-Xiong Dai
Summary: In this study, the synthesis of functionalized styrenes via palladium-catalyzed Suzuki-Miyaura cross-coupling reaction between aryl ketone derivatives and potassium vinyltrifluoroborate was reported. The use of pyridine-oxazoline ligand was essential for the cleavage of unstrained C-C bond. Various functional groups and biologically important molecules were well tolerated. The orthogonal Suzuki-Miyaura coupling demonstrated its synthetic practicability.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Applied
Zhong-Hua Sun, Wang Chen, Le-Yao Wang, Liang Wang, Yi-Han Tang, Bin-Bin Qian, Ming-Yang He, Qun Chen, Zhi-Hui Zhang
Summary: In this study, an effective metal-organic frameworks composite, Cu-BTC@Fe3O4, was used to catalyze Suzuki-Miyaura reaction with high yield under mild conditions. The catalyst exhibited excellent reusability and separability.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Editorial Material
Chemistry, Multidisciplinary
Soji Shimizu
Summary: Porphyrin analogues have attracted intensive investigations due to their rich coordination chemistry and unique optical and electrochemical properties. Among them, subporphyrins, especially the boron-free ones, have long been awaited. Recently, Kim, Osuka, and Song successfully synthesized a boron-free subporphyrin by introducing an exocyclic double bond at the meso-position and subsequent reduction to obtain macrocyclic conjugation. This seminal work will significantly facilitate studies on coordination chemistry and applications in materials science, as the availability of free base porphyrins is crucial for the development of porphyrin chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Rino Ishikawa, Ryosuke Iwasawa, Yuichiro Takiyama, Tomokazu Yamauchi, Tetsuo Iwanaga, Makoto Takezaki, Motonori Watanabe, Naozumi Teramoto, Toshiaki Shimasaki, Mitsuhiro Shibata
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Polymer Science
Kazuki Satoh, Takeshi Yokoyama, Toshiaki Shimasaki, Naozumi Teramoto, Mitsuhiro Shibata
JOURNAL OF POLYMER RESEARCH
(2016)
Article
Chemistry, Multidisciplinary
Martin C. Schwarzer, Ryosuke Konno, Takayulu Hojo, Alumichi Ohtsuki, Keisuke Nakamura, Ayaka Yasutome, Hiroaki Takahashi, Toshiaki Shimasaki, Mamoru Tobisu, Naoto Chatani, Seiji Mori
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Polymer Science
Ayaka Shibita, Toshiaki Shimasaki, Naozumi Teramoto, Mitsuhiro Shibata
Article
Polymer Science
Kaito Sugane, Hayato Takahashi, Toshiaki Shimasaki, Naozumi Teramoto, Mitsuhiro Shibata
Article
Chemistry, Organic
Toshiaki Shimasaki, Ryosuke Iwasawa, Motonori Watanabe, Naozumi Teramoto, Mitsuhiro Shibata
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Applied
Shinya Yano, Takumi Iwase, Naozumi Teramoto, Toshiaki Shimasaki, Mitsuhiro Shibata
CARBOHYDRATE POLYMERS
(2018)
Article
Chemistry, Organic
Kurumi Kobayashi, Rumiko Saito, Kaori Udagawa, Naoko Miyano-Kurosaki, Naoto Asano, Tetsuo Iwanaga, Naozumi Teramoto, Toshiaki Shimasaki, Mitsuhiro Shibata
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Polymer Science
Shima Aoyagi, Toshiaki Shimasaki, Naozumi Teramoto, Mitsuhiro Shibata
EUROPEAN POLYMER JOURNAL
(2018)
Article
Polymer Science
Kaito Sugane, Yoshiki Yoshioka, Toshiaki Shimasaki, Naozumi Teramoto, Mitsuhiro Shibata
Article
Chemistry, Organic
Toshiaki Shimasaki, Shunsuke Okajima, Rino Ishikawa, Shinji Kawaguchi, Takeshi Akimoto, Naoto Asano, Tetsuo Iwanaga, Motonori Watanabe, Naozumi Teramoto, Mitsuhiro Shibata
Article
Chemistry, Multidisciplinary
Toshiaki Shimasaki, Yuki Ohno, Mao Tanaka, Masato Amano, Yuta Sasaki, Hirobumi Shibata, Motonori Watanabe, Naozumi Teramoto, Mitsuhiro Shibata
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2019)
Article
Polymer Science
Shohei Matsuda, Ayaka Shibita, Toshiaki Shimasaki, Naozumi Teramoto, Mitsuhiro Shibata
Article
Chemistry, Multidisciplinary
Toshiaki Shimasaki, Ryota Kuroda, Misaki Akao, Takeshi Akimoto, Tenta Ishikawa, Tetsuo Iwanaga, Naozumi Teramoto, Mitsuhiro Shibata
Article
Chemistry, Organic
Toshiaki Shimasaki, Kurumi Kobayashi, Takayuki Kitanou, Tomohiro Oki, Tenta Ishikawa, Naoto Asano, Tetsuo Iwanaga, Naozumi Teramoto, Mitsuhiro Shibata
Summary: 3-(4-(Arylethynyl)phenyl)-7-(diethylamino)-2H-chromen-2-ones 1a-1d were synthesized via Pd/Cu-catalyzed Sonogashira cross-coupling reactions. Their photophysical properties, including fluorescence properties in different states, were systematically studied, revealing different fluorescence quantum yields. Theoretical and electrochemical studies showed the importance of compound structures in determining their fluorescence properties.