Article
Chemistry, Multidisciplinary
Ming Xu, Zhijun Wang, Zhaohui Sun, Yizhao Ouyang, Zhengwei Ding, Tao Yu, Liang Xu, Pengfei Li
Summary: This study developed a novel method for selective activation of a remote bond using a through-(hetero)arene radical transmission concept. By a metal-free [3+2] cycloaddition reaction, pyridine-substituted cyclopentanes, cyclopentenes, and bicyclo[2.1.1]hexanes that are difficult to access using known methods were synthesized. The reaction was catalyzed by a simple and inexpensive diboron(4) compound and proceeded via dearomative/rearomative processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Inorganic & Nuclear
Xusheng Guo, Chao Li, Weibo Wang, Yuanjun Hou, Baowen Zhang, Xuesong Wang, Qianxiong Zhou
Summary: The steric hindrance effect plays an important role in the activity improvement of water reduction catalysts. The replacement of a pyridine group in the TPA ligand by quinoline and isoquinoline can significantly enhance the H-2 evolution efficiency of polypyridyl Co complexes.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Janos Jozsef, Laszlo Somsak, Marietta Toth, Laszlo Juhasz
Summary: The [2+2] cycloadditions of methylene exo-glycal derivatives with chlorosulfonyl isocyanate and dichloroketene were investigated, studying the influence of the carbohydrate moiety, protecting groups, and reaction temperature on the yields of the transformations. New anomeric spiro-beta-lactam and spiro-cyclobutanone derivatives were obtained, and their structures were determined by 1D and 2D NMR and MS experiments. The transformation of spiro-cyclobutanone into spiro-gamma-lactone was also demonstrated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Xiaolan Li, Xiuqi Zhang, Fukuan Zhang, Xuzhong Luo, Haiqing Luo
Summary: In this study, a Mn(OAc)(2)-promoted formal dehydrative dehydroaromatizing [4 + 2] cycloaddition of enamides with maleimides was developed to construct pyridine rings and access diverse synthetically valuable pyrrolo [3,4-c]-pyridine derivatives. This method enables the formation of two C-C bonds for assembling pyridine derivatives from readily available enamides and inexpensive maleimides, demonstrating broad substrate scope and good functional group compatibility.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Yuan Liu, Shuang Lin, Yin Li, Jiang-Hao Xue, Qingjiang Li, Honggen Wang
Summary: This article reports a facile synthesis strategy for bicyclo[2.1.1]hexanes (BCHs) as bioisosteres of benzenoids in medicinal chemistry. The synthesis is achieved through a strain-release-driven [27r + 2o-] cycloaddition of bicyclo[1.1.0]butanes (BCBs) with alkenes using a pyridine-boryl radical catalyst. The mild reaction conditions, wide substrate scope, and good functional group tolerance make this protocol appealing for drug design and synthesis. Theoretical mechanistic studies suggest a radical relay mechanism, and synthetic applications of the products are demonstrated.
Article
Chemistry, Multidisciplinary
Wang Wang, M. Kevin Brown
Summary: In this study, we achieved the stereoselective construction of 3D bicyclic scaffolds and azetidine derivatives by modulating N-sulfonylimines, allowing for either [4+2]- or [2+2]-cycloaddition reactions. The utility of the method was demonstrated through further modulation of the resulting products. Mechanistic studies supported a reaction mechanism involving Dexter energy transfer.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Inorganic & Nuclear
Yuji Mikata, Mizuho Uchida, Hinata Koike, Sunao Shoji, Yutaka Ohsedo, Yasushi Kawai, Takashi Matsuo
Summary: Eighteen mononuclear copper(II) complexes with oxygen-containing N4O1 pentadentate ligands were synthesized and the effects of substitution of (iso)quinoline heteroaromatics at different positions on the properties of copper(II) complexes were investigated. The results indicate that the steric hindrance caused by the peri hydrogen atom in quinoline at the Ar-3 position enhances the coordination ability of quinoline nitrogen and ether oxygen atoms to the metal center. The quinoline substitution at the Ar-3 site exhibits an opposite effect compared with those at the Ar-1 and Ar-2 sites in the absorption spectra.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Organic
Sureshbabu Nallapati, Min-Feng Tseng, Pei-Ling Chen, Shih-Ching Chuang
Summary: A novel triphenylphosphine-mediated [4 + 3] annulation reaction of 2-benzylidene indane-1,3-diones and diynoates was discovered, resulting in biologically interesting indeno[1,2-b]oxepin-4-ylidenes with up to 75% yield. Single-crystal X-ray diffraction confirmed the separable Z and E isomeric oxepins.
Article
Chemistry, Physical
Yuan Liu, Shuang Lin, Yin Li, Jiang-Hao Xue, Qingjiang Li, Honggen Wang
Summary: A facile synthesis of bicyclo[2.1.1]hexanes (BCHs) via strain-release-driven [27r + 2o-] cycloaddition of bicyclo[1.1.0]butanes (BCBs) with alkenes is reported. The reaction is facilitated by a pyridine-boryl radical catalyst and exhibits mild reaction conditions, broad substrate scope, and decent functional group tolerance. Theoretical mechanistic studies reveal a radical relay mechanism, and synthetic applications of the products are demonstrated.
Article
Chemistry, Organic
Yanlin He, Wei Cai, You Huang
Summary: The Lewis-base-catalyzed enantioselective formal [4 + 2] annulation reaction of o-acylamino-aryl MBH carbonates and electron-deficient olefins was developed, leading to the synthesis of tetrahydroquinolines with three sequential stereogenic centers containing a quaternary stereocenter in high yields and good enantioselectivity.
Article
Chemistry, Multidisciplinary
Wasim Ahmed, Zi-Hao Huang, Zi-Ning Cui, Ri-Yuan Tang
Summary: This study reports the synthesis of unique mesoionic thiazoloisoquinolinium thiolates via cycloaddition reaction, which shows good bioactivity against the chlorophyll of duckweed.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Bernard Mravec, Simon Budzak, Miroslav Medved', Lukas F. Pasteka, Chavdar Slavov, Torben Sassmannshausen, Josef Wachtveitl, Jozef Kozisek, Lea Hegedusova, Juraj Filo, Marek Cigan
Summary: The design and synthesis of a set of 13 pyridine/quinoline hydrazones led to the discovery that the operational wavelengths of the pyridine hydrazone motif can be effectively shifted towards the visible region without loss of thermal stability. Introducing an electron-withdrawing pyridyl moiety or extending pi-conjugation in hydrazones can enhance thermal stability or shift absorption maxima towards the visible spectral region, without compromising photoswitching efficiency.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Shunqin Chang, Donghui Xing, Yuzhen Zheng, Liangbin Huang
Summary: A three-component cascade cyclization catalyzed by copper was used to synthesize quinoline-4-thiols using easily available diaryliodonium salts, alkynyl sulfides, and nitriles as starting materials. Sulfur atoms play a crucial role in controlling regioselectivity by stabilizing the high-valent vinyl copper intermediate. Additionally, the sulfide group at position 4 of quinoline can be further utilized as a transformable group for ipso-transformation and as a directing group for C-H functionalization, leading to the synthesis of various multifunctional quinoline derivatives.
Article
Chemistry, Multidisciplinary
De-Hai Liu, Kyogo Nagashima, Hui Liang, Xue-Lin Yue, Yun-Peng Chu, Shuming Chen, Jiajia Ma
Summary: This study introduces a highly chemoselective protocol for the reduction of quinoline and isoquinoline through selective energy transfer catalysis. The protocol bypasses the traditional metric of reduction reaction and relies on the triplet energies of chemical moieties and the kinetic barriers of energy and hydrogen atom transfer events. It retains many reducing labile functional groups that were previously incompatible.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jun Li, Scott R. Gilbertson
Summary: This study reports a diastereoselective [4 + 2] cycloisomerization of asymmetric allenyl dienes synthesized using Ma's method. These substrates undergo diastereoselective intramolecular rhodium catalyzed [4 + 2] cycloisomerization similar to thermal intramolecular Diels-Alder reactions, with diastereoselectivities ranging from 99:1 to 90:10 in most examples out of 29 presented.
Article
Chemistry, Organic
Shumpei Kanaya, Yuta Asaji, Tomoyuki Yoshimura, Jun-ichi Matsuo
Article
Chemistry, Organic
Mizuki Yamazaki, Tomoyuki Yoshimura, Jun-ichi Matsuo
Summary: 1,3-Cyclobutanediones reacted with aromatic aldehydes to produce cyclic beta-keto esters, catalyzed by a small amount of potassium ethoxide. The effects of alkoxide catalysts and spiro cyclic groups on the 1,3-cyclobutanediones were examined.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Hironori Takeuchi, Yusuke Fujimori, Yoshihiro Ueda, Hiromitsu Shibayama, Masaru Nagaishi, Tomoyuki Yoshimura, Takahiro Sasamori, Norihiro Tokitoh, Takumi Furuta, Takeo Kawabata
Article
Biochemistry & Molecular Biology
Misa Nishiyama, Noritaka Nakamichi, Tomoyuki Yoshimura, Yusuke Masuo, Tomoe Komori, Takahiro Ishimoto, Jun-ichi Matsuo, Yukio Kato
NEUROCHEMICAL RESEARCH
(2020)
Article
Chemistry, Organic
Tomoyuki Yoshimura, Yuki Enami, Jun-ichi Matsuo
SYNTHESIS-STUTTGART
(2020)
Article
Chemistry, Medicinal
Tomoyuki Yoshimura, Yuki Umeda, Risako Takahashi, Jun-ichi Matsuo
CHEMICAL & PHARMACEUTICAL BULLETIN
(2020)
Article
Chemistry, Medicinal
Mika Hanashima, Toshiki Matsumura, Yuta Asaji, Tomoyuki Yoshimura, Jun-ichi Matsuo
CHEMICAL & PHARMACEUTICAL BULLETIN
(2020)
Article
Chemistry, Organic
Kenta Sakamoto, Yuya Ikawa, Tomoyuki Yoshimura, Jun-ichi Matsuo
Summary: Metal-free cyclopropanation of N-protected indoles with alpha-aryl-alpha-diazoacetates was successfully achieved using triflic imide as a Bronsted acid catalyst. The addition of a catalytic amount of methyl phenylacetate improved the efficiency of the reaction. A proposed reaction mechanism involving C-protonation of diazoacetates with HNTf2, followed by formal [3+2] cycloaddition with indoles and 1,3-rearrangement, explains the success of the cyclopropanation reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Ayumi Imayoshi, Bhatraju Vasantha Lakshmi, Yoshihiro Ueda, Tomoyuki Yoshimura, Aki Matayoshi, Takumi Furuta, Takeo Kawabata
Summary: Since the discovery of mechanically planar chiral rotaxanes and topologically chiral catenanes, their asymmetric synthesis has been a long-standing challenge. Here, the authors report enantioselective preparation of mechanically planar chiral rotaxanes with up to 99.9% ee in 29% yield.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Tomoyuki Yoshimura, Kanta Chino, Jun-ichi Matsuo
Summary: A novel and concise synthesis method for 1,3,5-cycloheptatrienes has been developed, which can be achieved through mild reaction conditions and simple manipulations. The synthesis is advantageous due to its use of readily available reagents and moderate yields of the desired products.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Fuka Hori, Tomoyuki Yoshimura, Jun-ichi Matsuo
Summary: A novel method for the synthesis of 3-alkyl-2-arylindoles was developed through sequential oxidation and reduction reactions. Starting from 2-(2-nitrophenyl)ethanols prepared by a base-catalyzed three-component reaction, the desired products were obtained by oxidation and reduction steps. Notably, a selective synthesis of N-hydroxyindole was also achieved. Furthermore, the highly nucleophilic nature of transient benzylic anions in DMSO was demonstrated for the three-component reactions.
Article
Chemistry, Organic
Tomoyuki Yoshimura, Ken-ichi Onda, Jun-ichi Matsuo
Summary: An asymmetric synthesis method using an axially chiral arylaryne intermediate has been developed, which allows for the formation of chiral biaryl compounds while preserving the enantiomeric excess (ee) of the precursor. The high chiral transfer from precursor to product was observed at both low and room temperature.
Article
Chemistry, Organic
Tomoka Dentani, Ayano Kawachi, Misaki Kato, Tomoyuki Yoshimura, Jun-ichi Matsuo
Summary: In this study, the regioselectivity and stereoselectivity of intramolecular domino aldol cyclization/acetalizations of 1,2,7,8-tetraones were investigated using various catalytic agents. Good enantioselectivities were observed in the direct catalytic asymmetric cyclization of a 1,2,7,8-tetraone with chiral organocatalysts. Furthermore, the total synthesis of (+/-)-nesteretal A, a highly oxidized cage molecule, was accomplished using TiCl4-promoted anti-selective aldol cyclization of a symmetrical 1,2,7,8-tetraone as the key reaction.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Shunya Morita, Tomoyuki Yoshimura, Jun-ichi Matsuo
Summary: The three-component reactions of nitroalkanes, acrylamides, and aldehydes using catalytic amount of KOH in DMSO resulted in the formation of beta '-hydroxy-gamma-nitro amides. Mechanistic studies showed that the reactions proceeded through domino Michael/aldol reactions.
Article
Chemistry, Organic
Pan Yang, Tomoyuki Yoshimura, Takahiro Sasamori, Norihiro Tokitoh, Kazuhiro Morisaki, Takeo Kawabata
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)
