Article
Chemistry, Organic
Sundaramoorthi Sarathkumar, Veerababurao Kavala, Ching-Fa Yao
Summary: A water-soluble and low-valent rhenium(I) catalyst has been described for the C2 alkenylation of N-pyridyl/N-pyrimidyl indole derivatives with ynamides under mild conditions using water as the solvent. The reaction results in high yields of C2-Z-selective alkenylation products.
Article
Chemistry, Organic
Rajshekhar A. Unhale, Milon M. Sadhu, Vinod K. Singh
Summary: A novel organocatalytic asymmetric formal [3 + 2] cycloaddition has been developed for the synthesis of biologically relevant chiral spiroisoindolinone-indolines with excellent yields and enantioselectivity under mild conditions.
Article
Chemistry, Organic
Jiaqi Zhang, Weijie Xu, Weihui Zhuang, Ximan Chen, Xiaofeng Zhang, Qiufeng Huang
Summary: In this study, a rhodaelectro-catalyzed C2-H selectively decarboxylative alkenylation of 3-carboxy-1H-indoles using electricity as the traceless terminal oxidant has been achieved. The weakly coordinating carboxyl group serves as the traceless directing groups.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jie Ren, Chao Pi, Xiuling Cui, Yangjie Wu
Summary: A highly regioselective synthesis of 1-aminoisoquinolines was achieved through Rh(III)-catalyzed reactions, using imidamide as the directing group to achieve high selectivity. This strategy provides a new approach for the synthesis of biologically active 1-aminoisoquinolines.
Article
Chemistry, Multidisciplinary
Vinayak Hanchate, Sudharshan Nagabhushana Reddy, Anil Kumar, Kandikere Ramaiah Prabhu
Summary: The reactivity of sulfoxonium ylide with allyl carbonates and allyl carbamates diverges. Rh(iii)-catalyzed C-H activation and cyclization of sulfoxonium ylide with ally esters leads to the formation of a cyclopropane-fused tetralone derivative via cascade C-H activation, (4+2) annulation, and cyclopropanation. A similar reaction of sulfoxonium ylide with allyl carbamates forms a C3-substituted indanone derivative through a rare and interesting domino C-H activation and (4+1) annulation in which allyl carbamate acts as a C1-synthon.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Sujin Min, Taeeun Kim, Taejoo Jeong, Junhyeok Yang, Yebin Oh, Kyeongwon Moon, Amitava Rakshit, In Su Kim
Summary: The synthesis of functionalized carbazoles has become an important topic in drug discovery and material science. In this study, a rhodium(III)-catalyzed cross-coupling reaction between indolyl nitrones and 2-methylidene cyclic carbonate was disclosed, resulting in the formation of C2-formylated carbazoles. The synthetic utility of this protocol was demonstrated by various post-transformations of C2-formylated carbazoles.
Article
Chemistry, Multidisciplinary
Xiang-Ting Min, Ding-Wei Ji, Yu-Qing Guan, Shi-Yu Guo, Yan-Cheng Hu, Boshun Wan, Qing-An Chen
Summary: Transition metal catalyzed decarbonylation offers a unique synthetic strategy for new chemical bond formation. The study developed a visible light induced rhodium catalysis for decarbonylative coupling of imides with alkynes under ambient conditions, revealing the rhodium complex serves as both the catalytic center and photosensitizer. This visible light promoted catalytic decarbonylation strategy opens up new opportunities for re-evaluating old transformations with ligand dissociation as a rate-determining step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Sanjeev Kumar, Ajay K. Singh
Summary: The study presents the development of a visible-light-driven modular micro-flow reactor for the synthesis of a fused N-heteroaryl scaffold and late-stage functionalization of pyrazolopyridines. The method offers a simple and efficient approach without the need for expensive oxidants or additional photo-catalysts.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Man Zhu, Mengdie Zhu, Fangjie Wei, Chongjing Shao, Xingwei Li, Bingxian Liu
Summary: Bridged isoxazolidines were synthesized via Rh-(III)-catalyzed C-H allylation of alpha-aryl nitrones with 5-methylene-1,3-dioxan-2-one. The nitrone group acted as a directing group and 1,3-dipole in the C-H activation/[3 + 2] cycloaddition cascade, showing excellent chemo- and stereoselectivity as well as good functional group compatibility. The resulting compounds' skeletal structure could be conveniently modified and applied in the synthesis of biologically active molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hai-Shan Jin, Cai-Cai Liang
Summary: This study reports an efficient synthesis of isoindolinone-derived spiroisochromenes using a [3 + 3] annulation of 3-aryl-3-hydroxyisoindolinones. In this Rh(iii)-catalyzed spirocyclization reaction, vinylene carbonate acts as a three-atom synthon (C-C-O) through decarboxylation. This atom-economic reaction undergoes through a C-H activation pathway under mild conditions and represents the first example of using 3-aryl-3-hydroxyisoindolinones as building blocks for constructing spiroheterocycles.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Prakriti Dhillon, Prasad Anaspure, Jesper G. Wiklander, Subban Kathiravan, Ian A. Nicholls
Summary: The regiochemical outcome of a cobalt(ii) catalysed C-H activation reaction of aminoquinoline benzamides with unsymmetrical 1,3-diynes under relatively mild reaction conditions can be controlled by the choice of diyne. The choice of diyne allows access to either 3- or 4-hydroxyalkyl isoquinolinones, facilitating the synthesis of more complex isoquinolines.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Qinghe Gao, Zhenhua Sun, Qinfei Xia, Ruonan Li, Wenlong Wang, Siwei Ma, Yixin Chai, Manman Wu, Wei Hu, Peter Abranyi-Balogh, Gyorgy M. Keseru, Xinya Han
Summary: A new general synthesis method has been developed to prepare pharmaceutically important azolo[1,5-a]pyrimidines starting from commonly available 3(5)-aminoazoles, aldehydes, and triethylamine. This direct and practical strategy allows the construction of a variety of compounds, including pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines, with the capability to synthesize zaleplon, a clinically used drug.
Article
Chemistry, Organic
Lin Xiao, Xu-Ge Liu, Mei-Zhu Bao, Jia-Lin Song, Shao-Yong Chen, Yi-Chuan Zheng, Yan-Zhi Liu, Shang-Shi Zhang
Summary: The Cp*Rh(III)-catalyzed nitro-directed C-H alkylation/alkenylation of nitroarenes has been reported for the first time. This method exhibits high efficiency, broad substrate scope, and good functional group compatibility. Gram-scale experiments and synthetic applications confirmed the practicality of this method. Furthermore, preliminary mechanistic investigations consistently indicated that C-H bond cleavage is the rate-limiting step.
Article
Chemistry, Organic
Qi-Liang Yang, Yi-Rui Luo, Rong-Yi Xu, Bei-Ning Zhang, Yan-Ni Zhang, Hai-Ming Guo
Summary: A sustainable pathway for the synthesis of tetracyclic purinium salts via ruthenium-catalyzed electro-oxidative annulation of C-6-arylpurine nucleosides with alkynes without a stoichiometric metal oxidant has been developed. The protocol exhibits high regioselectivity, broad scope, and wide functional group tolerance, allowing efficient coupling of various biologically important molecules. A novel purinoisoquinolinium-coordinated ruthenium(0) sandwich intermediate has been isolated, crystallographically characterized, and electrochemically analyzed, offering direct mechanistic insight.
Article
Chemistry, Organic
Vikki N. Shinde, Krishnan Rangan, Dalip Kumar, Anil Kumar
Summary: A Rh(III)-catalyzed dehydrogenative annulation and spirocyclization of 2-arylindoles and 2-(1H-pyrazol-1-yl)-1H-indole with maleimides has been developed, providing highly functionalized compounds. The reaction methodology has broad substrate scope, good functional group tolerance, and is simple and scalable. The annulated product of 2-(1H-pyrazol-1-yl)-1H-indole showed significant red-shift and high absorption and emission values compared to 2-phenylindole.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yasunori Minami, Yuki Furuya, Tatsuro Kodama, Tamejiro Hiyama
Article
Chemistry, Multidisciplinary
Takeshi Komiyama, Yasunori Minami, Tamejiro Hiyama
Article
Chemistry, Multidisciplinary
Yasunori Minami, Tamejiro Hiyama
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Multidisciplinary
Takeshi Komiyama, Yasunori Minami, Tamejiro Hiyama
Article
Chemistry, Multidisciplinary
Takahiro Kato, Takuya Kuwabara, Yasunori Minami, Tamejiro Hiyama, Youichi Ishii
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2019)
Article
Chemistry, Organic
Keisuke Uchida, Yasunori Minami, Suguru Yoshida, Takamitsu Hosoya
Article
Chemistry, Multidisciplinary
Yasunori Minami, Yuki Furuya, Tamejiro Hiyama
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
Marti Gimferrer, Massimo Christian D'Alterio, Giovanni Talarico, Yasunori Minami, Tamejiro Hiyama, Albert Poater
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Physical
Yasunori Minami, Hitomi Miyamoto, Yumiko Nakajima
Summary: Furfural and its derivatives were subjected to alkenylation with alkynes via alpha-C-H activation in the presence of a palladium/carboxylic acid catalyst, leading to the formation of corresponding single and double alkenylated products while maintaining the reactivity of the aldehyde group. This catalytic system enabled selective alkenylation of furan substrates with electron-withdrawing substituents.
Article
Chemistry, Organic
Yasunori Minami, Nao Matsuyama, Yasuaki Matsuo, Masanori Tamura, Kazuhiko Sato, Yumiko Nakajima
Summary: A new method is presented in this study for the reductive cleavage of the solvent-insoluble poly(phenylene sulfide) main chain using triethylsilane as a hydrogen source under palladium/IcHex catalytic conditions. Efficient formation of benzene and bis(triethylsilyl) sulfide as a sulfide source was observed after the reaction. This method is suitable for gram-scale operations.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Physical
Nai-Yuan Jheng, Yusuke Ishizaka, Yuki Naganawa, Yasunori Minami, Akira Sekiguchi, Kosuke Iizuka, Yumiko Nakajima
Summary: This study demonstrates the radical hydrodehalogenation of aryl halides using a Co(I) catalyst under atmospheric pressure, with a mechanistic study revealing the involvement of PNNP-Co complex and long-range metal-ligand cooperation. The reaction is applicable to various aryl bromides and aryl chlorides.
Article
Chemistry, Organic
Akira Nagai, Akihiro Kobayashi, Yuki Sakata, Yasunori Minami, Keisuke Uchida, Takamitsu Hosoya, Suguru Yoshida
Summary: A new method for synthesizing multifunctionalized arenes from simple phenols using aryne intermediates is described. The aryne precursors were prepared from phenols through various transformations, and the highly functionalized aryne intermediates were used to synthesize multisubstituted arenes.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Yasunori Minami, Nao Matsuyama, Yasuo Takeichi, Ryota Watanabe, Siby Mathew, Yumiko Nakajima
Summary: Insoluble polyetheretherketone can be depolymerized using sulfur nucleophiles to form benzophenone dithiolate and hydroquinone, which can then be converted into various dithiofunctionalized benzophenones using organic halides. This depolymerization method is not affected by the shape of polyetheretherketone and can be used for carbon- or glass fiber-enforced polyetheretherketone materials.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yasunori Minami, Yuuki Inagaki, Tomoo Tsuyuki, Kazuhiko Sato, Yumiko Nakajima
Summary: This study investigates the depolymerization of oxyphenylene super engineering plastics using cesium hydroxide as a hydroxy source and calcium hydride as a dehydration agent. The reaction takes place in 1,3-dimethyl-2-imidazolidinone and effectively produces hydroxylated monomers. High yields of 4,4'-(sulfonyldiphenol) and 4,4'-(propane-2,2-diyl)diphenol were obtained in the case of polysulfone, and similar results were observed for other super engineering plastics such as polyethersulfone, polyphenylsulfone, and polyetheretherketone.
Article
Chemistry, Multidisciplinary
Yuya Tamura, Yasunori Minami, Yoshitake Nishiyama, Yuki Sakata, Fumika Karaki, Takamitsu Hosoya, Suguru Yoshida
CHEMICAL COMMUNICATIONS
(2020)
