Article
Chemistry, Multidisciplinary
Hwangseok Kim, Jaeho Lee, Taehyun Kim, Minyoung Cho, Tae-Lim Choi
Summary: In this study, the authors demonstrate the versatile application of living Suzuki-Miyaura catalyst-transfer polymerization (SCTP) using a RuPhos Pd G3 precatalyst for the precise synthesis of various donor-acceptor alternating conjugated polymers (DA ACPs). The method allows for the controlled synthesis of DA ACPs with controlled molecular weight, narrow dispersity, and high yield. The authors also successfully synthesized block copolymers and demonstrated the tunable optical and electronic properties of the resulting polymers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Polymer Science
Ryota Iwamori, Ryota Sato, Junpei Kuwabara, Takaki Kanbara
Summary: Nonstoichiometric polyaddition was achieved through Co-catalyzed hydroarylation of diyne monomers with excess 1-(2-pyrimidinyl)pyrrole. The 2-pyrimidinyl substituent acted as a directing group, facilitating intramolecular catalyst transfer and yielding poly(arylenevinylene)s with alkyne terminals and high molecular weight.
Article
Multidisciplinary Sciences
Lara E. Zetzsche, Jessica A. Yazarians, Suman Chakrabarty, Meagan E. Hinze, Lauren A. M. Murray, April L. Lukowski, Leo A. Joyce, Alison R. H. Narayan
Summary: This study demonstrates the use of cytochrome P450 enzymes for biocatalytic cross-coupling reactions, enabling the formation of sterically hindered biaryl bonds through oxidative C-C bond formation. By engineering the substrate and atroposelectivity of the P450 enzyme, a highly efficient and selective process has been developed.
Article
Chemistry, Physical
Lu Ye, Xiaojing Liu, Yangcheng Lu
Summary: In this study, a highly efficient palladium catalyst was successfully immobilized on the surfaces of magnetic nanoparticles with the coordination of N-heterocyclic carbene. The catalyst showed outstanding catalytic performance in the Suzuki-Miyaura cross-coupling reaction and good recyclability after being reused multiple times. The prepared Pd-NHC@NCPs could be conveniently separated from the reactions system with an external magnet, displaying promising potential for practical applications.
JOURNAL OF CATALYSIS
(2021)
Article
Polymer Science
Busra Nakipoglu, Cansu Aydogan, Mucahit Ozdemir, Yusuf Yagci, Sermet Koyuncu, Baris Kiskan
Summary: This study presents a simple and efficient method for synthesizing conjugated poly(phenylene butadiynylene) (PPB) polymers using photo-induced radical homocoupling. The resulting PPB polymers exhibited a red shift in the optical properties and a decrease in the band gap and oxidation potential. Transmission electron microscopy and atomic force microscopy measurements revealed the self-organization of the PPB polymers into planar 2D nanorods, supported by density functional theory calculations. The surface area of the polymer was determined to be 53.61 and 30.69 m(2)/g using Brunauer-Emmett-Teller and Barrett-Joyner-Halenda methods, respectively.
Article
Chemistry, Multidisciplinary
Hamed M. Alshammari, Obaid F. Aldosari, Mohammad Hayal Alotaibi, Raja L. Alotaibi, Mosaed S. Alhumaimess, Moataz H. Morad, Syed Farooq Adil, Mohammed Rafi Shaik, Mohammad Shahidul Islam, Mujeeb Khan, Abdulrahman Alwarthan
Summary: Pd/C catalysts on activated carbon with varying palladium content showed high catalytic activity for Suzuki-Miyaura coupling reactions and Mizoroki-Heck cross-coupling reactions. The catalyst with 3% Pd/C demonstrated better efficiency and reusability compared to other synthesized catalysts, indicating the significance of high 'Pd' content and uniform impregnation on the catalyst activity.
APPLIED SCIENCES-BASEL
(2021)
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
Jie Xu, Samantha Grosslight, Kyle A. Mack, Sierra C. Nguyen, Kyle Clagg, Ngiap-Kie Lim, Jacob C. Timmerman, Jeff Shen, Nicholas A. White, Lauren E. Sirois, Chong Han, Haiming Zhang, Matthew S. Sigman, Francis Gosselin
Summary: An efficient asymmetric synthesis of a potent KRAS G12C covalent inhibitor, GDC-6036, was reported. The synthesis involved a highly selective Negishi coupling and a series of reaction sequences, leading to the desired compound with a 40% overall yield from the starting materials.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Materials Science, Paper & Wood
Arnet Maria Antony, Masira Imtiyaz Chamanmalik, Vishal Kandathil, Harini G. Sampatkumar, B. S. Sasidhar, C. V. Yelamaggad, Siddappa A. Patil
Summary: A new N-heterocyclic carbene-palladium(II) complex grafted on cellulose was synthesized as a heterogeneous catalyst. The structure, morphology, thermal stability and chemical composition of the catalyst were confirmed by various analytical techniques. The catalyst exhibited excellent catalytic ability in Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, with good tolerance to various functional groups and easy recovery by filtration.
Article
Chemistry, Multidisciplinary
Timothy B. Boit, Milauni M. Mehta, Junyong Kim, Emma L. Baker, Neil K. Garg
Summary: This study presents a new method for adding two different nucleophiles to the carbonyl carbon of an amide in a single step, leading to the conversion of amides to chiral alcohols. The use of non-precious-metal catalysis enables this one-pot process, potentially allowing for the development of new transformations converting carboxylic acid derivatives to functional groups with stereogenic centers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Han Shen, Jingyi He, Feng He, Yurui Xue, Yongjun Li, Yuliang Li
Summary: In this study, N-doped graphdiyne was synthesized as the support for metal nanoparticles by bottom-up approach from tetraethynylpyrazine. The specific introduction of pyridine nitrogen atoms in the N-doped carbon material makes it a promising material for supporting ultrafine metal particles or clusters. Microwave-assisted anchoring of Pd, Pt, Cu, Ni nanoparticles on NGDY generated novel hybrid composites with Pd-NGDY showing high versatility for Suzuki-Miyaura reaction.
APPLIED CATALYSIS A-GENERAL
(2021)
Article
Chemistry, Multidisciplinary
P. S. Pharande, G. S. Rashinkar, D. M. Pore
Summary: A novel cellulose-supported Schiff base Pd(II) complex was successfully designed and synthesized, showing high catalytic activity and reusability in the Suzuki Miyaura cross-coupling of phenyl boronic acid and aryl halides. The method exhibited high TONs and TOFs, low catalyst loading, and the synthesis of novel biphenyl derivatives.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
Article
Polymer Science
Laura Riva, Gloria Nicastro, Mingchong Liu, Chiara Battocchio, Carlo Punta, Alessandro Sacchetti
Summary: This article highlights the importance of designing and synthesizing durable heterogeneous catalysts from renewable sources derived from biomass waste. It presents an efficient method for loading Pd(II) ions on a cellulose-based organic support, as well as the application and recycling performance of this support in Suzuki-Miyaura coupling reactions.
Article
Nanoscience & Nanotechnology
Sheng Guo, Yifan Wu, Shao-Xiong Lennon Luo, Timothy M. Swager
Summary: Heterogeneous catalysts with confined nanoporous catalytic sites exhibit high activity and size selectivity, making them suitable for the preparation of intermediates in the synthesis of pharmaceutical agents. Compared to homogeneous catalysts, heterogeneous systems show size-dependent catalytic activity with bulkier substrates and can be used to create catalytic impellers that simplify their use and recovery.
ACS APPLIED NANO MATERIALS
(2022)
Article
Chemistry, Physical
Yahao Dong, Zhangquan Zhou, Yanan Wang, Xinjuan Li, Tao Li, Yihang Ren, Wendi Hu, Linbo Zhang, Xinhui Zhang, Chunyan Wei
Summary: In this study, a new hypercrosslinked polymer supported palladium catalyst was synthesized and characterized. The catalyst exhibited high efficiency in the preparation of biphenyl compounds with low catalyst loading. It also showed advantages in terms of availability of raw materials, stability, and cost-effectiveness.
JOURNAL OF MOLECULAR LIQUIDS
(2022)
Article
Polymer Science
Masataka Nojima, Takeru Kamigawara, Yoshihiro Ohta, Tsutomu Yokozawa
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
(2019)
Article
Chemistry, Organic
Ko Urushibara, Tatsunori Yamada, Akihiro Yokoyama, Hirotoshi Mori, Hyuma Masu, Isao Azumaya, Hiroyuki Kagechika, Tsutomu Yokozawa, Aya Tanatani
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Polymer Science
Takayoshi Katoh, Tomoya Suzuki, Yoshihiro Ohta, Tsutomu Yokozawa
Summary: Reversible polycondensation through an alkoxide-catalyzed ester-ester exchange reaction is an effective strategy for synthesizing telechelic polymers free from contamination with cyclic polymers. The use of an exchange reagent can lead to telechelic polymers with multiple functional end-groups, while the conventional polycondensation route often results in cyclic polymers formation.
Article
Polymer Science
Takayoshi Katoh, Yoshihiro Ohta, Tsutomu Yokozawa
Summary: This study investigated the ester-ester exchange reaction of poly(methyl acrylate) (PMA) with alkyl formate or polyester catalyzed by alkoxide. The results showed that different groups could be efficiently introduced into PMA through the transesterification reaction. In addition, a method for preparing graft copolymers by polycondensation and ester exchange reaction was explored.
JOURNAL OF POLYMER SCIENCE
(2022)
Article
Polymer Science
Takayoshi Katoh, Maai Saso, Yoshihiro Ohta, Tsutomu Yokozawa
Summary: We described a method of synthesizing polycarbonate through ester-carbonate exchange reaction, and achieving the exchange reaction between PC and other polymers under specific conditions. The composition of PC and PEs in the copolymer can be adjusted, and increasing polymerization degree leads to higher melting temperature of the copolymer.
Article
Polymer Science
Yoshihiro Ohta, Chih-Feng Huang, Yi-Huan Lee, Chi-An Dai, Tsutomu Yokozawa
Summary: Well-defined block copolymers consisting of hyperbranched polyamide and polystyrene were synthesized and their self-assembled structures in solutions were investigated. The morphology of the resulting copolymers varied with different compositions and solvent conditions, including the formation of spherical micelles and vesicles.
MACROMOLECULAR CHEMISTRY AND PHYSICS
(2023)
Article
Polymer Science
Tsuyoshi Namekawa, Hajime Sugita, Yoshihiro Ohta, Tsutomu Yokozawa
Summary: Cyclic polymers with different backbones were selectively synthesized using a non-stoichiometric Suzuki-Miyaura polycondensation reaction. This reaction involved the use of 1.0 equivalent of diboronate monomers containing carbon-carbon double bond (C=C), ester, ether, and carbonate linkages with 1.3 equivalents of meta- or para-dibromophenylene, in the presence of t-Bu3PPd G2 precatalyst and CsF/18-crown-6 as a base. The obtained cyclic polymers showed an increase in molecular weight with increasing monomer concentration. The presence of C=C bonds in the polymer was confirmed even at high molecular weights through end-group analysis after a degradative cross-metathesis reaction.
EUROPEAN POLYMER JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Hajime Sugita, Takeru Kamigawara, Sou Miyazaki, Ryusuke Shimada, Takayoshi Katoh, Yoshihiro Ohta, Tsutomu Yokozawa
Summary: This study investigates intramolecular catalyst transfer on benzoheterodiazoles in Suzuki-Miyaura coupling reactions and polymerization reactions. It is found that the Pd catalyst undergoes intramolecular transfer on dibromobenzotriazole, whereas intermolecular transfer occurs in part in the case of dibromobenzoxazole and is predominant for dibromobenzothiadiazole. In the polymerization reactions, different benzoheterodiazoles react with phenylenediboronates to produce high-molecular-weight polymer and cyclic polymer, with dibromobenzoxazole resulting in a moderate-molecular-weight polymer with bromine at both ends.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Yu Tokita, Tatsuya Uchida, Takeru Kamigawara, Kenta Hoka, Reo Nitto, Yoshihiro Ohta, Tsutomu Yokozawa
Summary: This study successfully introduced various functional groups at both ends of P3HT polymer through successive catalyst-transfer condensation polymerization and coupling reactions in one pot, and synthesized a polymer with a base-sensitive functional group.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Yu Tokita, Tatsuya Uchida, Takeru Kamigawara, Kenta Hoka, Reo Nitto, Yoshihiro Ohta, Tsutomu Yokozawa
Summary: In this study, polymeric materials with functional groups at both ends were synthesized via successive Kumada catalyst-transfer polycondensation and Suzuki coupling reaction in one pot, expanding the synthetic methods for functionalized polymers.
CHEMICAL COMMUNICATIONS
(2023)
Article
Polymer Science
Takayoshi Katoh, Yukiko Ogawa, Yoshihiro Ohta, Tsutomu Yokozawa
Summary: The ester-ester exchange reaction proved to be faster than the ester-alcohol exchange reaction, leading to the successful synthesis of high-molecular-weight polyesters under various conditions. The copolymerization of different compounds through ester-ester exchange also resulted in the formation of new copolymers with confirmation from C-13 NMR spectroscopy and DSC thermal analysis.
JOURNAL OF POLYMER SCIENCE
(2021)
Article
Polymer Science
Hajime Sugita, Yoshihiro Ohta, Tsutomu Yokozawa
JOURNAL OF POLYMER SCIENCE
(2020)
Article
Polymer Science
Ryouichi Okabayashi, Yoshihiro Ohta, Tsutomu Yokozawa
Article
Polymer Science
Yoshihiro Ohta, Yuji Abe, Kenta Hoka, Eisuke Baba, Yu-Ping Lee, Chi-An Dai, Tsutomu Yokozawa
Article
Polymer Science
Hajime Sugita, Masataka Nojima, Yoshihiro Ohta, Tsutomu Yokozawa