Article
Chemistry, Multidisciplinary
Dan-Xia Zhao, Guo-Ping Lu, Chun Cai
Summary: The development of a Co and Ce-doped BiOCl and Bi2O2CO3 composite material has shown high photocatalytic activity under white LED irradiation, allowing for efficient platinum-promoted coupling reactions at room temperature with a high yield.
Article
Chemistry, Multidisciplinary
Huai-Qing Yang, Qian-Qian Chen, Fulai Liu, Rui Shi, Yong Chen
Summary: Monodispersed palladium phosphide (Pd3P) was successfully utilized in the photocatalytic Suzuki coupling reaction under visible light irradiation, with CdS nanoflake acting as a photosensitizer. The heterogeneous system demonstrated high yields of products and excellent stability in alcohol solvent at room temperature.
CHINESE CHEMICAL LETTERS
(2021)
Article
Nanoscience & Nanotechnology
Xueyan Sun, Shaofeng Li, Jinzhe Cao, Yuchao Wang, Wenbo Yang, Lijing Zhang, Yijin Liu, Jieshan Qiu, Shengyang Tao
Summary: The integration of catalytic production and separation of biphenyl (with a purity of 99.7%) was successfully achieved by combining Suzuki cross-coupling reactions and crystallization separation. A hierarchical-structured impeller loaded with Pd nanoparticles on Ni(OH)(2) nanosheets catalyzed the reactions with high turnover frequency (TOF) value of 25,976 h(-1) and a yield of 99.5%. X-ray absorption fine structure (XAFS) analysis revealed that enhanced catalytic activity was due to electron transfer between the Pd nanoparticles and Ni(OH)(2).
ACS APPLIED MATERIALS & INTERFACES
(2021)
Review
Chemistry, Multidisciplinary
Shelesh Krishna Saraswat, Ramanjaneyulu Seemaladinne, Media Noori Abdullah, Halim Zaini, Nabeel Ahmad, Nafis Ahmad, Esmail Vessally
Summary: Aryl fluorosulfates are versatile building blocks in organic synthesis and have gained increasing attention in SuFEx click chemistry. They can be easily prepared from phenols using low-cost sulfuryl fluoride as a sulfonyl fluoride provider. They have been used as less toxic and more atom economical alternatives to triflates in numerous cross-coupling reactions. This review summarizes the recent advances and developments in utilizing aryl fluorosulfates as electrophilic partners in cross-coupling reactions.
Article
Polymer Science
Yuehui Yuan, Zhiyi Song, Masayoshi Bando, Tamaki Nakano
Summary: By catalyzing benzene amine and ketone composites with zinc vapor and 2,2’-biphenyl doping, benzylamine porous organic crystals are formed, which exhibit excellent performance in gas adsorption and selective dye adsorption.
Article
Chemistry, Organic
Hirokazu Seto, Takumi Tono, Akiko Nagaoka, Mai Yamamoto, Yumiko Hirohashi, Hiroyuki Shinto
Summary: Poly(vinylbiphenyl)s bearing glycoside ligands at the side chains were prepared using the Suzuku coupling reaction. The effects of glycoside reactant concentration, halide species, glycoside species, and catalyst species on the incorporation of glycoside ligand into the polymer were investigated. The obtained glycopolymers exhibited specific binding to proteins corresponding to the glycoside ligands and showed fluorescent properties due to the biphenyl spacers formed during the Suzuki coupling reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Materials Science, Multidisciplinary
Khaoula Oudghiri, Lahoucine Bahsis, Said Eddarir, Hafid Anane, Moha Taourirte
Summary: A green protocol for the in situ synthesis of Pd nanoparticles on chitosan beads (Pd NPs-CS) without toxic reducing agents was reported. The Pd nanoparticles catalyst was prepared by a simple coordination reaction between chitosan beads and palladium ions. The Pd NPs-CS catalyst showed high catalytic activity and selectivity in Suzuki-Miyaura cross-coupling reaction and Heck reaction, with the bead form of the catalyst easily separated from the reaction mixture.
Article
Materials Science, Paper & Wood
Zhian Xu, Jinxi Xu, Waner Zheng, Yiqun Li
Summary: A novel and efficient cellulose-based Pd@Cell-EDTA catalyst was easily prepared through the esterification of cellulose with ethylenediaminetetraacetic dianhydride and subsequent coordination with PdCl2. The Pd@Cell-EDTA catalyst showed excellent activity in Suzuki reactions and Sonogashira reactions, and it could be reused multiple times without significant loss of catalytic performance.
Article
Materials Science, Paper & Wood
Pouya Ghamari Kargar, Milad Nayebi, Zahra Parhizi, Rajender S. Varma
Summary: An eco-friendly approach was used to generate Ni nanoparticles on a magnetized cellulose biopolymer, resulting in a core-shell type nanocomposite (Fe3O4@CNF@Ni). The nanocomposite was characterized using various advanced techniques and its catalytic performance was evaluated in the synthesis of biaryl derivatives. The results showed that the nanocomposite exhibited high stability and catalytic efficiency.
Article
Chemistry, Multidisciplinary
Anindita Dewan, Manashi Sarmah, Prantika Bhattacharjee, Pankaj Bharali, Ashim J. Thakur, Utpal Bora
Summary: This study reports the design, synthesis, and application of naturally occurring cellulose from agro waste pomegranate peel as a novel support for active biogenic Pd nanoparticles for Suzuki-Miyaura and Sonogashira cross-coupling reactions at room temperature. The cellulose matrix enables well dispersion of Pd nanoparticles over the support to generate Pd@cellulose, exhibiting excellent catalytic activity and recyclability under ligand-free mild reaction conditions. The synthesized cellulose nanofibers and Pd-anchored heterogeneous nanofibers were characterized through various analytical techniques.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2021)
Article
Chemistry, Multidisciplinary
Weixu Lu, Xiaoqiang Yu, Ming Bao
Summary: In this paper, a group of copper-based ternary deep eutectic solvents (Cu-DESs) were synthesized and applied in Glaser-type homo- and cross-coupling of terminal alkynes. These reactions occurred under exogenous-ligand-free, base-free, and additive-free conditions, providing satisfactory to excellent yields (up to 99%) under mild conditions. The Cu-DESs can be recycled eight times, with water being the only by-product, complying fully with the principles of green chemistry.
Review
Chemistry, Physical
Gianluigi Albano, Antonella Petri, Laura Antonella Aronica
Summary: In recent years, there has been extensive research on immobilizing palladium nanoparticles on solid supports for the preparation of active and stable catalytic systems. Compared to inorganic materials, naturally occurring organic solids are more cost-effective and readily available. This review focuses on the application of metal catalysts supported by natural biomaterials in C-C bond formation reactions, specifically Mizoroki-Heck, Suzuki-Miyaura, and Sonogashira reactions. Different types of organic matrices, such as cellulose, starch, pectin, agarose, chitosan, as well as proteins and enzymes, are discussed, highlighting the heterogeneous nature and recyclability of each catalyst.
Review
Chemistry, Physical
Brijesh S. Kadu
Summary: Palladium has been widely used in the Suzuki-Miyaura cross coupling reaction for over 30 years, but it comes with drawbacks such as high cost, tedious work-ups, product contamination, and metal leaching. In recent years, other metals like Ni, Cu, Co, Fe, Rh, and Ru have attracted attention for their potential in SMCR, allowing for the synthesis of industrially important compounds with various functional groups. This review discusses recent advancements in catalysis related to SMCR, providing valuable insights for researchers in designing synthetic protocols for pharmacophores and drug molecules.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Organic
Samantha L. Gargaro, Bre'Shon Dunson, Joshua D. Sieber
Summary: The Suzuki-Miyaura cross-coupling reaction of 2-bromo-1,3-bis(trifluoromethyl)benzene with arylboronic acids leads to the formation of significant amounts of boronic acid homocoupling products, especially with electron-deficient arylboronic acids. Good yields of cross-coupling products can be achieved by utilizing dicyclohexyl(2',6'-dimethoxybiphenyl-2-yl)phosphine (SPhos) as the ligand.
Article
Chemistry, Organic
Shoaib Iqbal, Muhammad Sharif, Peter Langer
Summary: This review discusses the importance and impact of Suzuki-Miyaura coupling reactions of fluorinated arenes in chemical and biological research, as well as their applications in various aspects.
Article
Chemistry, Organic
Na Li, Baozhen Sun, Shuang Liu, Jinbo Zhao, Qian Zhang
Article
Chemistry, Organic
Jiqiang Gao, Chunhui Liu, Zhongjuan Li, Haotian Liang, Yuhui Ao, Jinbo Zhao, Yuchao Wang, Yuanqi Wu, Yu Liu
Article
Chemistry, Medicinal
Wei Zhou, Dongyan Ju, Yuhui Ao, Yu Liu, Jinbo Zhao
Summary: The synthesis and antiproliferative activity of a series of structurally diverse nitrone derivatives were reported, with indole- and pyrrole-fused analogues further evaluated through analogue preparation and in-vitro screening. Analogues with moderate to good potency were identified, showing promise for further pursuit of nitrone-type small molecules in chemotherapy.
MEDICINAL CHEMISTRY RESEARCH
(2021)
Article
Chemistry, Organic
Min Zhang, Jiqiang Gao, Jinbo Zhao, Tingtian Qiu, Zhongjuan Li, Ziteng Guo, Chunhui Liu, Yu Liu
Summary: An unprecedented Fe-catalyzed ring-opening reaction of simple cyclobutanones has been developed, allowing for the synthesis of conjugated enones with good functional group tolerance in high yields under mild conditions. Product derivatization and gram-scale experiments further demonstrated the synthetic utility of the reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Tengyun Chen, Yunkai Wu, Peilin Han, Jiqiang Gao, Yuanqi Wu, Jinbo Zhao, Haotian Liang, Yongsheng Liu, Yu Liu
Summary: We have developed a nickel catalyzed C-C bond reconstruction method using H2O as a hydrogen donor, which enables the conversion of o-bromophenylcyclobutanones into indanones and further synthesis of benzene-fused cyclic compounds.
HELVETICA CHIMICA ACTA
(2022)
Article
Chemistry, Organic
Jie Zhang, Peng Yan, Zhichao Wang, Jinbo Zhao, Qin Chen, Ping Lu
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Chao Hou, Yan Ma, Yongqi Zhang, Huiling Xu, Yuanqi Wu, Jinbo Zhao, Yuchao Wang, Yu Liu
Summary: In this paper, an efficient system based on inexpensive nickel catalyst and phosphine ligand for the cyclotrimerization of various internal esteryl alkynes is described. The regioselectivity of the protocol can be precisely controlled, providing a series of polysubstituted benzene rings mainly composed of 1,2,4-isomers.
HELVETICA CHIMICA ACTA
(2022)
Article
Chemistry, Organic
Bowen Liu, Lei Wang, Yunfei Qin, Xianxiu Xu, Jinbo Zhao
Summary: In this study, a Lewis-base-catalyzed three-component electrophilic thiofunctionalization was developed for the synthesis of trisubstituted chromanes. This metal-free protocol offers high trans-diasteroselectivity and a unique substitution pattern, enabling access to the otherwise inaccessible chromane chemical space that is important for medicinal chemistry campaigns.
Article
Chemistry, Organic
Xiao Yu, Zhihong Ma, Wenjing Zhu, Hongyan Liu, Zenghui Zhang, Yi Liu, Mei Zhang, Jinbo Zhao, Pengfei Zhang, Chengcai Xia
Summary: A novel route for the synthesis of derivatives of benzothiadiazine/1-(phenylsulfonyl)-1H-benzimidazole has been developed, utilizing a SnCl2-promoted tandem reduction, ammonolysis, condensation, and deamination reaction. The method offers convenient operation, good functional group tolerance, and employs unsensitive and inexpensive SnCl2/i-PrOH as the reaction reagent, providing a direct approach for the synthesis of pharmaceutically important targets.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Yi Liu, Wenjing Zhu, Xiao Yu, Hongyan Liu, Zenghui Zhang, Mei Zhang, Jinbo Zhao, Yacong Wang, Chengcai Xia
Summary: A method for synthesizing dihydropyrazoles has been developed, featuring mild reaction conditions and good functional group tolerance.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Na Li, Biqiong Hong, Jinbo Zhao, Zhenhua Gu
Summary: This study developed a practical method for the synthesis of phenanthridines through ring-expansion reaction, and successfully synthesized optically active planar chiral ferrocenyl phenanthridines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Mei Zhang, Xiao Yu, Wenjing Zhu, Yi Liu, Zenghui Zhang, Jinbo Zhao, Chengcai Xia, Ke Li
Summary: A novel iron-catalyzed tandem sulfonylation, C(sp2)-H activation, cyclization reaction has been developed to synthesize derivatives of (Z)-2-phenyl-4-((phenylsulfonyl)methylene)-3,4-dihydro-2H-benzo[e][1,2]thiazine 1,1-dioxide using N-phenyl-N-(prop-2-yn-1-yl)benzenesulfonamide and benzenesulfonylhydrazide. This method offers convenient operation, good functional group tolerance, and utilizes inexpensive FeSO4 as the catalyst, providing a direct approach for the preparation of benzothiazides.
Article
Chemistry, Organic
Chuang Zhao, Ah-Ying Dong, Dongyan Ju, Jianhong Huang, Ran Jia, Yu Liu, Jinbo Zhao
Summary: This paper presents the Pd-catalyzed coupling cyclization of delta,epsilon-alkenyl oxime with (hetero)aryl and halides, which results in the synthesis of seven-membered N,O-heterocycles, tetrahydro-1,2-oxezapines, in moderate to good yields. DFT calculation supports an outer-sphere anti-oxypalladation pathway and provides important insights into the reaction mechanism. This reaction represents an unprecedented example of heterocyclization leading to the formation of a seven-membered ring.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Mengru Zhang, Hexin Li, Jinbo Zhao, Yan Li, Qian Zhang
Summary: We have developed a novel copper-catalyzed cyclization method, to efficiently synthesize a series of α,α-difluoro-β-lactams under mild reaction conditions. This represents the first example of utilizing a metal carbene intermediate as the C1 synthon for [3 + 1] cyclization to synthesize β-lactams.
Article
Chemistry, Organic
Bowen Liu, Guochun Peng, Yu Zhang, Chunhui Liu, Jinbo Zhao
Summary: The Cu(i)-catalyzed ring-opening cross-coupling of an oxabicyclic olefin with an organoboron reagent leads to the formation of cis-2-aryl-1,2-dihydronaphthalen-1-ol derivatives, differing from the trans-selectivity observed in similar Cu-catalyzed reactions with Grignard reagents. DFT calculations indicate a possible alternative pathway involving boronic ester by-product assisted ring-opening, instead of the canonical beta-oxygen elimination, as the rate-determining step.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
