Review
Chemistry, Organic
Linqing Wang, Haiyong Zhu, Tianyu Peng, Dongxu Yang
Summary: Conjugated ynones are versatile substrates with unique reactivity, compatible with various catalytic conditions, making them important tools for asymmetric synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Koichi Mitsudo
Summary: Electrochemical reactions are gaining attention as powerful and environmentally friendly methods for organic synthesis. By electro-oxidizing palladium acetate, efficient cationic palladium species can be obtained, facilitating coupling reactions between arylboronic acids and terminal alkynes, as well as cross-coupling reactions using an Ag anode. Additionally, sequential reaction systems that switch between oxidative and neutral conditions with the use of electricity can produce multiple pi-extended butadiynes in one step.
Article
Biochemistry & Molecular Biology
Xinjuan Li, Zhangquan Zhou, Yanan Wang, Jiaxin Dong, Xianbin Jia, Zhiguo Hu, Qingcong Wei, Weiwei Zhang, Yuqin Jiang, Jiaojiao Zhang, Yahao Dong
Summary: Starch-SB serves as a supporting material for palladium stabilization, resulting in a new air and moisture-stable palladium composite (Starch-SB-Pd(II)). This composite shows high activity and stability in Suzuki cross-coupling reactions due to the cooperative interactions between multifunctional capturing sites on starch and palladium species. The experiments also demonstrate the recyclability of this starch-supported catalytic system.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Chemistry, Organic
Yongjie Yang, Kai Jiang, Hua Zhu, Biaolin Yin
Summary: A mild, step-economical method for the synthesis of highly conjugated functionalized 2-pyridones is reported, which involves Pd-catalyzed reactions of alkynes with carbon nucleophiles. Some of the 2-pyridones have been shown to absorb shortwave radiation, indicating potential utility for filtration of such radiation.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Kiyoshi Tanemura
Summary: The addition of small amounts of dioxane and water was beneficial in solvent-free Suzuki-Miyaura cross-coupling reactions. Various solid and liquid aryl bromides and chlorides reacted with boronic acids in the presence of 1 mol% of Pd(OAc)2 and 2 mol% of RuPhos at 25°C to yield the corresponding biaryls with good to excellent yields. The reactions of aryl chlorides were faster than those of aryl bromides. 0.2 mol% of Pd(OAc)2 was sufficient for the reactions of some aryl chlorides. This procedure is particularly useful for the reactions of aryl chlorides.
Article
Chemistry, Organic
Giorgio Rizzo, Gianluigi Albano, Teresa Sibillano, Cinzia Giannini, Roberta Musio, Fiorenzo G. Omenetto, Gianluca M. Farinola
Summary: This paper reports the application of a silk fibroin-supported Palladium catalyst (Pd/SF) in Suzuki-Miyaura and Ullmann coupling reactions of aryl chlorides. The existence of catalytic pockets where monoatomic palladium species can form stable complexes with SF is hypothesized and supported by experimental analysis. The size of the catalytic pocket of Pd/SF is estimated to be approximately 15 angstroms using computational modeling.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Guang-Yan Xing, Ya-Cheng Zhu, Deng-Yuan Li, Pei-Nian Liu
Summary: On-surface synthesis, a powerful tool for atomically precise fabrication of low-dimensional carbon nanomaterials, has greatly enriched fundamental science and technology. Achieving high selectivity of covalent coupling reactions remains challenging due to the complicated reactivity of organic groups and irreversibility of covalent bonds. Only a few on-surface covalent coupling reactions are frequently used, and this Perspective focuses on the development and synthetic applications of on-surface cross-coupling reactions.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Ilja Rodstein, Leif Kelling, Julian Loffler, Thorsten Scherpf, Abir Sarbajna, Diego M. Andrada, Viktoria H. Gessner
Summary: The use of simple PdCl2 complexes stabilized through a unique bonding motif with ylide-substituted phosphines (YPhos) as efficient precatalysts has improved the efficiency of C-X cross-coupling reactions.
Article
Chemistry, Organic
Yuye Bai, Zhenyuan Lin, Zhenying Ye, Dian Dong, Jing Wang, Lu Chen, Feng Xie, Yibiao Li, Pierre H. Dixneuf, Min Zhang
Summary: In this study, we describe a ruthenium-catalyzed regioselective hydrohalogenation reaction of alkynes under mild conditions. Commercially simple halogen sources such as KI, ZnBr2, and ZnCl2 were employed for this transformation. The reaction was also applicable to alkynes derived from bioactive molecules, showing the potential synthetic value of this new reaction in organic synthesis.
Article
Chemistry, Organic
Arun D. R. Shada, Hari P. R. Mangunuru, Leila Terrab, Srinivasarao Tenneti, Nageswara Rao Kalikinidi, Santhosh Reddy Naini, Praveen Gajula, Emily B. Crull, Venumadhav Janganati, Raghavendra Kovvuri, Vasudevan Natarajan, Daniel Lee, Jinya Yin, Lalith Samankumara, Rohit Mahar, Xueyi Zhang, Anji Chen, Chathuranga C. Hewa-Rahinduwage, Zhirui Wang, Manasa Mamunooru, Jagruti Rana, Chaitanya S. Wannere, Joseph D. Armstrong III, R. Thomas Williamson, Gopal Sirasani, Bo Qu, Chris H. Senanayake
Summary: We report the use of a new class of highly effective benzooxaphosphole-based, water-soluble ligands in Suzuki-Miyaura cross-coupling reactions for sterically hindered substrates in aqueous media. The addition of catalytic amounts of organic phase transfer reagents significantly enhances the catalytic activities of the coupling reactions. This new Suzuki-Miyaura protocol demonstrates the synthesis of important building blocks, including heterocycles, for biologically active compounds.
Article
Chemistry, Multidisciplinary
Di Zhang, Youyuan Xiong, Yingjie Guo, Lei Zhang, Zheng Wang, Kuiling Ding
Summary: In this study, a Pd-catalyzed enantioselective domino Heck carbonylation reaction was developed using o-iodoacrylanilides, terminal alkynes, and water as nucleophiles. The reaction afforded a diverse range of beta-carbonylated 2-oxindole derivatives with a 3,3-disubstituted all-carbon quaternary stereocenter in high yields and good to excellent enantioselectivities. The synthetic utility of the methodology was demonstrated through gram-scale synthesis of various compounds, showcasing its potential for efficient chiral 2-oxindole synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Liyan Fu, Jingwen You, Yasushi Nishihara
Summary: This method utilizes a palladium catalyst to synthesize unsymmetrical biaryls by cross-coupling acyl chlorides with potassium perfluorobenzoates under redox-neutral conditions. Compared to traditional methods, this synthetic strategy allows for the easy preparation of reactants from inexpensive aromatic carboxylic acids.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Ryan Q. Tran, Long P. Dinh, Seth A. Jacoby, Nekoda W. Harris, William A. Swann, Savannah N. Williamson, Rebecca Y. Semsey, Larry Yet
Summary: 3-Aryl-1-phosphinoimidazo[1,5-a]pyridine ligands were synthesized through two different pathways using 2-aminomethylpyridine as the starting material, involving cyclization, iodination, and palladium-catalyzed cross-coupling phosphination reactions. These ligands were then evaluated in palladium-catalyzed sterically-hindered biaryl and heterobiaryl Suzuki-Miyaura cross-coupling reactions.
Article
Chemistry, Multidisciplinary
Sheng Zhang, Junchao Yin, Ziyang Wang, Yang Li, Yukang Fu, Ji Ma, Zhilong Xie, Ming Bao
Summary: A palladium-catalysed aromative benzylic allylation and allenylation of benzyl chlorides with allyl and allenyl pinacolborates is reported for the first time. The reactions are conducted smoothly in the presence of a bidentate phosphine ligand, yielding good cross-coupling products. This new synthetic method exhibits excellent tolerance for various functional groups and is compatible with sensitive groups such as NO2, CF3, CN, and COOMe. The utilization of a bidentate ligand and heating is crucial for the transformation. DFT calculation results reveal the importance of wide-bite-angle bidentate ligands for the formation of an eta(1)-benzyl-eta(1)-allylpalladium intermediate and the thermodynamic favorability of the normal coupling reaction.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Faezeh Khosravi, Ander Centeno-Pedrazo, Fatemeh Rajabi, Thomas Len, Leonid G. Voskressensky, Rafael Luque, Eduardo J. Garcia-Suarez
Summary: Carbon-carbon coupling reactions are of great interest for various applications. The use of greener solvents and heterogeneous metal catalysts is desirable. This study successfully synthesized biaryl compounds in water using carbon-supported Pd nanoparticles, achieving shorter reaction time. The utilization of TOP or TPP ligands slowed down Pd leaching. Additionally, a treatment with H2O2 was beneficial for improving the hydrophilicity of the carbon support. These results and methodology contribute to a greener future for C-C coupling reactions.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2022)
Article
Chemistry, Multidisciplinary
Masayuki Iwasaki, Jie Xu, Yukari Tani, Liyan Fu, Yuichi Ikemoto, Yasuyuki Ura, Yasushi Nishihara
Article
Chemistry, Organic
Keita Hyodo, Shuhei Nishinaga, Yuta Sawanaka, Takumi Ishida, Hiroki Mori, Yasushi Nishihara
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Biochemistry & Molecular Biology
Xiu Wang, Zhenhua Wang, Li Liu, Yuya Asanuma, Yasushi Nishihara
Article
Chemistry, Organic
Zhenhua Wang, Xiu Wang, Yasuyuki Ura, Yasushi Nishihara
Article
Chemistry, Organic
Masayuki Iwasaki, Kosei Nonaka, Song Zou, Yuta Sawanaka, Takaaki Shinozaki, Tomoya Fujii, Kiyohiko Nakajima, Yasushi Nishihara
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Review
Chemistry, Multidisciplinary
Zhenhua Wang, Xiu Wang, Yasushi Nishihara
CHEMISTRY-AN ASIAN JOURNAL
(2020)
Article
Chemistry, Organic
Liyan Fu, Qiang Chen, Zhenhua Wang, Yasushi Nishihara
Article
Biochemistry & Molecular Biology
Takumi Ishida, Yuta Sawanaka, Ryota Toyama, Zhenfei Ji, Hiroki Mori, Yasushi Nishihara
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2020)
Article
Chemistry, Organic
Xiu Wang, Zhenhua Wang, Takumi Ishida, Yasushi Nishihara
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Liyan Fu, Qiang Chen, Yasushi Nishihara
Article
Biochemistry & Molecular Biology
Zhenfei Ji, Zeliang Cheng, Hiroki Mori, Yasushi Nishihara
Article
Chemistry, Organic
Jianjun Shi, Yuki Hayashishita, Toshikazu Takata, Yasushi Nishihara, Satomi Niwayama
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Qiang Chen, Liyan Fu, Yasushi Nishihara
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Xiu Wang, Zhenhua Wang, Yasushi Nishihara
CHEMICAL COMMUNICATIONS
(2019)
Article
Materials Science, Multidisciplinary
Yuya Asanuma, Hiroki Mori, Ryosuke Takahashi, Yasushi Nishihara
JOURNAL OF MATERIALS CHEMISTRY C
(2019)
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)
