Article
Chemistry, Organic
Chonglong He, Yipeng Zhou, Zhanhuan Li, Jianfeng Xu, Xingkuan Chen
Summary: This study reports a novel N-heterocyclic carbene (NHC) catalyzed formal [3 + 3] cycloaddition reaction, leading to the successful synthesis of benzofuran fused delta-lactams with good yields and enantioselectivities. Further gram-scale preparation and synthetic transformation of the cycloadducts demonstrate good practicality and applicability of this beta-carbon functionalization reaction.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Teruhisa Tsuchimoto, Takahiro Johshita, Kazuhiro Sambai, Naoki Saegusa, Takumi Hayashi, Tomohiro Tani, Mana Osano
Summary: A new method for the formation of seven-membered carbon rings in heteroarylindoles reacting with different substrates was discovered in this study, and the two different annulation reactions could be controlled. The resulting tetracyclic products can be further extended through subsequent reactions to expand the p-conjugated region.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Soshi Nishino, Koji Hirano
Summary: A copper-catalyzed regio- and diastereoselective borylacylation reaction has been developed to synthesize β'-boryl-β-ketoesters with high anti-diastereoselectivity. The reaction can also be extended to borylcarbamoylation, and enantioselective variants have been achieved using chiral phosphoramidite-ligated copper complexes.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Zubao Gan, Deyun Cui, Hongyun Zhang, Ying Feng, Liying Huang, Yingying Gui, Lu Gao, Zhenlei Song
Summary: The Hosomi-Sakurai allylation of allylsilanes with beta,gamma-unsaturated alpha-ketoesters has been successfully catalyzed by (Ph3C)[BPh((F))(4)] to afford gamma,gamma-disubstituted alpha-ketoesters in high yields and excellent chemoselectivity. Preliminary mechanistic studies indicate that the trityl cation is the major contributor to the catalysis, with the silyl cation playing a minor role.
Article
Chemistry, Organic
Ting Yao, Jia Li, Changgui Zhao
Summary: AnNHC-catalyzed enantioselective annulation reaction between enals and activated ketone is reported. This approach involves a [3 + 2] annulation of homoenolate with activated ketone and a subsequent ring expansion of γ-lactone by the nitrogen atom of indole. The method demonstrates a broad substrate scope, providing the corresponding DHPIs products in moderate to good yields and excellent levels of enantioselectivities. Controlled experiments have been conducted to elucidate a plausible mechanism.
Review
Chemistry, Organic
Shuhui Li, Xiaoxuan Li, Hui Yao, Mengting Tan, Dan Xu, Nianyu Huang, Nengzhong Wang
Summary: Straight-chain omega-amino-alpha, beta-unsaturated carbonyl compounds are versatile organic synthons with important applications in organocatalysis. This review discusses the recent applications of these synthons in covalent catalysis, non-covalent catalysis, and bifunctional catalysis.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Kosuke Higashida, Valentin Smail, Haruki Nagae, Jean-Francois Carpentier, Kazushi Mashima
Summary: We achieved a nickel(0)-catalyzed asymmetric allylic alkylation reaction of beta-dicarbonyl compounds under ambient conditions, resulting in high yields of quaternary chiral compounds with high enantioselectivity.
Article
Chemistry, Organic
Sushanta Kumar Parida, Saurav Joshi, Sandip Murarka
Summary: A copper-catalyzed efficient method has been developed for synthesizing a diverse variety of substituted N-aryl pyrazoles using readily available α,β-alkynic N-tosyl hydrazones and diaryliodonium triflates. This one-pot multi-step methodology demonstrates broad scope, good yields, scalability, and tolerance towards different functional groups. Control experiments reveal that the reaction proceeds through tandem cyclization/deprotection/arylation events with the distinct role of the copper catalyst.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Gaochen Xu, Huan Yan, Sai Zhang, Qinghuan Wu, Jindian Duan, Kai Guo
Summary: A new method using FeCl2 as catalyst for [4+2] annulation of alpha,beta-unsaturated ketoxime acetates with N-acetyl enamides in batch and flow processes is reported. This strategy features a low-cost catalytic system, use of electron-rich olefins, operational simplicity, and broad substrate scope, providing a facile and efficient access to substituted pyridines in moderate to good yields.
Article
Chemistry, Physical
Pu-Fan Qian, Tao Zhou, Jun-Yi Li, Yi-Bo Zhou, Bing-Feng Shi
Summary: Chiral benzothiadiazine-1-oxides are sulfur-stereogenic compounds with structural diversity that have gained significant attention in drug discovery. This study reports the synthesis of these chiral molecules through an asymmetric [4 + 3] annulation reaction of sulfoximines with alpha,beta-unsaturated ketones, catalyzed by an achiral Ru(II) complex and assisted by a chiral carboxylic acid (CCA). The method allows for the preparation of a wide range of chiral benzothiadiazepine-1-oxides with various functional groups in high yields and excellent enantioselectivity, expanding the chemical space of chiral sulfoximines. Importantly, the oxidative cleavage of the products yields chiral N-benzoyl sulfoximines with a C-S chiral axis.
Article
Chemistry, Organic
Tao Zhang, Shichong Wang, Dandan Zuo, Jingjing Zhao, Wen Luo, Chaojie Wang, Pan Li
Summary: A palladium-catalyzed carbonylative [5+1] cycloaddition reaction of N-tosyl vinylaziridines with CO has been developed, providing a practical and efficient method for synthesizing different types of δ-lactams. The choice of solvent allows for control over the type of lactam produced. Additionally, this method exhibits excellent step- and atom-economy and shows higher regioselectivity towards [5+1] cycloaddition.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Pawan S. Dhote, Chepuri Ramana
Summary: The [Au]-catalyzed nitroalkyne cycloisomerization process leading to anthranils may be affected by the trapping of the postulated intermediate alpha-oxo gold carbene with external nucleophiles. This study also provides evidence for the synthesis of highly functionalized indazoles through sequential bond formations.
Article
Chemistry, Organic
Le-Song Wu, Yi Ding, Ye-Qiang Han, Bing-Feng Shi
Summary: The paper describes an asymmetric C-H activation strategy for accessing alpha,beta-stereospecific gamma-lactams in good yields with high enantio- and diastereoselectivities, serving as an effective supplement to existing strategies.
Article
Chemistry, Physical
Kosuke Higashida, Valentin Smail, Haruki Nagae, Jean-Francois Carpentier, Kazushi Mashima
Summary: We successfully achieved nickel(0)-catalyzed asymmetric allylic alkylation (AAA) of beta-dicarbonyl compounds under ambient conditions by activating unstrained C-C bonds of 2-allylated 2-methylcyclohexane-1,3-dione derivatives. The reaction produced quaternary chiral compounds with high yield and enantioselectivity. The mechanism of the AAA reaction with the Ni(0)-(S)-tol-MeO-BIPHEP catalyst system was elucidated through control experiments and DFT calculations.
Article
Chemistry, Organic
Yan Jiang, Song Xi, Qi Wang, Lin Fu, Ling He, Zhen Wang, Min Zhang
Summary: A formal two-carbon insertion reaction into β-ketoesters with vinylmetal has been developed for the rapid synthesis of α'-ketoesters. This method features high efficiency, simple operation, and mild conditions without the usage of bases or catalysts.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Yuma Aoki, Takahiro Toyoda, Hiroto Kawasaki, Hikaru Takaya, Akhilesh K. Sharma, Keiji Morokuma, Masaharu Nakamura
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Kohei Iwai, Hiroshi Yamagishi, Colin Herzberger, Yuji Sato, Hayato Tsuji, Ken Albrecht, Kimihisa Yamamoto, Fumio Sasaki, Hiroyasu Sato, Aswin Asaithambi, Axel Lorke, Yohei Yamamoto
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Victor Bonal, Marta Morales-Vidal, Pedro G. Boj, Jose M. Villalvilla, Jose A. Quintana, Naiti Lin, Shoya Watanabe, Hayato Tsuji, Eiichi Nakamura, Maria A. Diaz-Garcia
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2020)
Article
Chemistry, Inorganic & Nuclear
Takahiro Iwamoto, Yoshiyuki Mizuhata, Norihiro Tokitoh, Masaharu Nakamura
Article
Chemistry, Multidisciplinary
Samara Medina Rivero, Rui Shang, Hiroyoshi Hamada, Qifan Yan, Hayato Tsuji, Eiichi Nakamura, Juan Casado
Summary: The study focused on electron acceptor and donor spiro-conjugated dimers based on specific compounds, investigating the existence of SOMO-HOMO energy level inversion through the radical forms of charged species. The results showed non-Aufbau energy properties in certain radical ions, attributed to spiro-conjugation and electron-electron repulsion effects.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2021)
Article
Chemistry, Physical
Katsuhiro Isozaki, Ryo Ueno, Kosuke Ishibashi, Genta Nakano, Haozhi Yin, Kenta Iseri, Masanori Sakamoto, Hikaru Takaya, Toshiharu Teranishi, Masaharu Nakamura
Summary: This study describes the synthesis of gold nanoclusters functionalized by peptide dendron thiolate ligands to form a hydrogen bonding supramolecular reaction field. The prepared nanoclusters act as efficient photocatalysts for oxidative cyclization, with dynamic transformation of hydrogen bonds between ligands playing a key role in accelerating the reaction. The concept introduced in this work allows for tuning reactivities and selectivities of metal nanocluster catalysts using supramolecular reaction fields created with dendritic thiolate ligands.
Review
Chemistry, Multidisciplinary
Hayato Tsuji
Summary: Carbon-bridged oligo(phenylenevinylene)s (COPVs) have a rigid planar molecular structure, excellent functionality and high stability, and exhibit phenomena at room temperature that conventional molecules only show at cryogenic temperatures.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2022)
Article
Chemistry, Organic
Keisuke Iwata, Yasunobu Egawa, Katsunori Yamanishi, Hayato Tsuji
Summary: The acid-induced intramolecular cyclization of 1,1-disubstituted 3-aryl-2,3-dibromoallylalcohols leads to the formation of 2,3-dibromo-1H-indene derivatives and tetrabromodihydro-s-indacenes. These multi-brominated compounds can serve as versatile building blocks for the synthesis of various indene and indacene derivatives. The synthesis of dialkylmethylene-bridged oligo(phenylenevinylene)s demonstrates the attractive photophysical properties of these compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Hayato Tsuji, Masaki Nakahata, Mafumi Hishida, Hideki Seto, Ryuhei Motokawa, Takeru Inoue, Yasunobu Egawa
Summary: This study investigates the aggregation behavior of hydrophobic solutes in water-THF solution and the role of THF. A model is proposed based on experimental results, suggesting that hydrophobic solutes are molecularly dispersed in the low-water-content region and form mesoscopic particles upon increasing the water fraction.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Materials Science, Multidisciplinary
Hayato Tsuji, Akihiro Shitomi, Naoto Hamaguchi, Yasunobu Egawa, Victor Bonal, Pedro G. Boj, Jose M. Villalvilla, Jose A. Quintana, Maria A. Diaz-Garcia
Summary: A naphtho[2,1-b:6,5-b ']difuran derivative has been identified as an effective violet-emitting laser dye, showing amplified spontaneous emission at 413 nm in polystyrene film. Lasing was also demonstrated using all-polymeric distributed-feedback lasers emitting at 411-417 nm.
JOURNAL OF MATERIALS CHEMISTRY C
(2021)
Article
Chemistry, Multidisciplinary
Takeru Inoue, Makoto Tsurui, Hiroshi Yamagishi, Yuma Nakazawa, Naoto Hamaguchi, Shoya Watanabe, Yuichi Kitagawa, Yasuchika Hasegawa, Yohei Yamamoto, Hayato Tsuji
Summary: In this study, donor-acceptor-donor conjugates were synthesized and found to serve as efficient and stable long-wavelength photoluminescent dyes in organic and aqueous media. Specifically, Cz-COPV2-BBTz-COPV2-Cz showed high photoluminescence quantum yield in the near-infrared region.
Article
Materials Science, Multidisciplinary
Victor Bonal, Jose M. Villalvilla, Jose A. Quintana, Pedro G. Boj, Naiti Lin, Shoya Watanabe, Karolis Kazlauskas, Ona Adomeniene, Saulius Jursenas, Hayato Tsuji, Eiichi Nakamura, Maria A. Diaz-Garcia
ADVANCED OPTICAL MATERIALS
(2020)
Article
Chemistry, Organic
Ryosuke Agata, Siming Lu, Hiroshi Matsuda, Katsuhiro Isozaki, Masaharu Nakamura
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Takahiro Iwamoto, Chiemi Okuzono, Laksmikanta Adak, Masayoshi Jin, Masaharu Nakamura
CHEMICAL COMMUNICATIONS
(2019)
Review
Chemistry, Organic
Hayato Tsuji, Eiichi Nakamura
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2020)