Article
Chemistry, Physical
Li-Ming Zhang, Wenjun Luo, Jiangzhen Fu, Yu Liu, Junliang Zhang
Summary: A newly developed PNP-type W-Phos ligand showed a unique effect on the catalytic asymmetric addition of reactive Grignard reagents to ketimines. This enabled a Cu(I)-catalyzed asymmetric alkylation reaction of N-sulfonyl ketimines, resulting in the formation of optically active α-tertiary amines with high enantioselectivities.
Article
Chemistry, Multidisciplinary
Wenjun Luo, Li-Ming Zhang, Zhan-Ming Zhang, Junliang Zhang
Summary: A novel family of PNP ligands (W-Phos) was designed and applied in the copper-catalyzed asymmetric addition of linear Grignard reagents to aryl alkyl ketones. This method allows for the facile synthesis of versatile chiral tertiary alcohols with high yields and excellent enantioselectivities. It also has the potential for the synthesis and modification of various densely functionalized medicinally relevant molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Giuseppe Dilauro, Francesco Messa, Fabio Bona, Serena Perrone, Antonio Salomone
Summary: A simple cobalt complex, Co(phen)Cl₂, has been found to be a highly efficient and cost-effective precatalyst for various cross-coupling reactions involving aromatic and aliphatic organoaluminum reagents with aryl, heteroaryl, and alkyl bromides. New C(sp²)-C(sp²) and C(sp²)-C(sp³) bonds can be formed in good to excellent yields and high chemoselectivity under mild reaction conditions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Zeng-Hua Wu, Huai-Yu Wang, Huai-Lan Yang, Li-Hua Wei, Tamio Hayashi, Wei-Liang Duan
Summary: An iridium-catalyzed asymmetric synthesis of branched allylic phosphine compounds with excellent stereoselectivity and regioselectivity is reported. The use of phosphine sulfides with low deactivation capacity is crucial for the success of this reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Chuntao Zhong, Mengna Liu, Xianchao Qiu, Hao Wei, Benqiang Cui, Yanhui Shi, Changsheng Cao
Summary: A nickel-catalyzed cross-coupling reaction between aryl methyl sulfides and aryl bromides has been developed to efficiently access biaryls. The method has a wide scope of substrates and is scalable, with commercially available aryl bromides being used without the need for preparation of organometallic reagents. This reaction has high application value.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Qi Zhang, Si-Wei Zhou, Chang-Yun Shi, Liang Yin
Summary: A catalytic asymmetric allylic substitution using copper(I) homoenolates as nucleophiles has been achieved, with high yields and enantioselectivity. The method is applicable to a broad range of substrates and can be extended to the construction of chiral quaternary carbon centers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Ruben Perez Sevillano, Franck Ferreira, Olivier Jackowski
Summary: Access to enantioenriched tertiary and quaternary α-chiral allysilanes without any transition-metal catalyst is achieved by enantioselective allylic displacement. This process involves Lewis base activation of Grignard reagents using a bidentate chiral NHC ligand and shows high β-regio- and enantioselectivity, while being compatible with various silyl groups on the substrates.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Hao Xu, Cai-Yu He, Bo-Jie Huo, Jia-Wen Jing, Chengping Miao, Weidong Rao, Xue-Qiang Chu, Xiaocong Zhou, Zhi-Liang Shen
Summary: In this study, a cross-electrophile coupling of aryl thiols with aryl bromides was reported, where C-S bond activation occurred instead of S-H bond cleavage, leading to the formation of thioethers as the major products. The reaction proceeded effectively with a nickel catalyst, magnesium turnings, and lithium chloride in THF at room temperature, and a variety of structurally diverse biaryls were obtained in moderate to good yields.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Meng-Die Li, Zi-Han Wang, Hui Zhu, Xin-Ru Wang, Jia-Run Wang, Tao-Yan Lin
Summary: In this study, the first remote enantioselective copper-catalyzed sulfonylation of yne-allylic esters with sodium sulfinates was reported. The method demonstrated practicality and attractiveness due to the use of readily available starting materials, mild reaction conditions, excellent selectivity, and broad substrate scope.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Kaiting Zheng, Yaomei Liu, Chenggong Zheng, Fangpei Yan, Hua Xiao, Yi-Si Feng, Shilu Fan
Summary: A palladium-catalyzed monofluoroalkylation method using nucleophilic ethyl 2-fluoro-2-(trimethylsilyl)acetate as a monofluoroalkyl source was developed. The reaction exhibited excellent substrate scope, providing a range of monofluoroalkylated products in good yields under mild conditions. This protocol was successfully applied in the late-stage modification of an estrone derivative, offering a facile route for the discovery of biologically active compounds and high-performance materials.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Yuichi Kobayashi, Takayuki Hirotsu
Summary: This study demonstrates the efficiency of a copper-catalyzed substitution of secondary propargylic phosphates by synthesizing (S)-Nyasol. The key phosphate was synthesized and substituted with stereo- and regioselectivity at the propargylic position. The resulting product was further transformed into (S)-nyasol with excellent selectivity.
Article
Chemistry, Organic
Ikuya Fujii, Kazuhiko Semba, Yoshiaki Nakao
Summary: Rhodium-aluminum bimetallic complexes catalyze the Kumada-Tamao-Corriu (KTC) cross-coupling reaction using arylmagnesium compounds generated from corresponding aryl fluorides or chlorides. This method allows the challenging KTC coupling reaction to be carried out using aryl fluorides as nucleophiles, resulting in various biaryls.
Article
Chemistry, Organic
Xin Fu, Tingting Ran, Yu Zhou, Jie Liu
Summary: Here, a facile and efficient electrochemical promoted Ni-catalyzed reductive carbon-carbon bond formation is reported. This Nicatalyzed modular approach shows good functional group tolerance and broad substrate scope. It enables the synthesis of a series of allylic compounds, including various structurally complex natural products and pharmaceutical motifs.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Shengtong Niu, Yingkun Luo, Chao Xu, Jinggong Liu, Shuang Yang, Xinqiang Fang
Summary: In this work, a general protocol for copper-catalyzed allylic substitutions using stable soft nucleophiles has been developed, resulting in the synthesis of highly selective functionalized 1,3- and 1,4-enynes. Mechanistic studies propose a copper acetylide-bonded allylic cation as the key intermediate, featuring an outer-sphere nucleophilic attack. The demonstrated diversified reactivities in this study will inspire further exploration.
Article
Chemistry, Applied
Madhawee K. Arachchi, Hien M. Nguyen
Summary: A broadly applicable methodology has been developed for the regio- and enantioselective construction of branched allylic carbon-heteroatom bonds from racemic, secondary allylic trichloroacetimidates. The products containing allylic C-O, C-N, and C-S bonds are obtained in synthetically useful yield and selectivity. Additionally, the chiral diene-ligated iridium catalyst is effective at promoting asymmetric aminations of acyclic secondary anilines.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Plant Sciences
Mariko Baba, Ken-ichi Yamada, Michiho Ito
Article
Chemistry, Organic
Kohta Yamasaki, Akiho Yamauchi, Tsubasa Inokuma, Yasunori Miyakawa, Yinli Wang, Raphael Oriez, Yousuke Yamaoka, Kiyosei Takasu, Naonobu Tanaka, Yoshiki Kashiwada, Ken-ichi Yamada
Summary: The study confirmed an enantioselective intramolecular migrative cyclization reaction, where the use of chiral nucleophiles led to enantiomerically enriched products.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ken-ichi Yamada, Shinichi Fujiwara, Tsubasa Inokuma, Masayuki Sugano, Yousuke Yamaoka, Kiyosei Takasu
Summary: DFT calculations provided a new model to rationalize stereoselectivity in asymmetric addition reactions, which is strongly supported by the diastereoselectivity in the reactions of a tetramethyldioxolanyl radical with various alkyl 8-phenylmenthyl benzylidenemalonates.
Article
Chemistry, Medicinal
Mohamed G. Thabit, Amany S. Mostafa, Khalid B. Selim, Magda A. A. Elsayed, Magda N. A. Nasr
Summary: In this study, pyrimidinone derivatives were synthesized based on modulation of the monastrol scaffold and were found to exhibit potent anticancer activity. Compound 5j showed the highest cytotoxic activity against four cancer cell lines, while being safe for normal human cells. Compounds 3d, 3e, and 5h-j demonstrated high Eg5 inhibitory activity. Cell cycle distribution analysis revealed that compound 5j arrested cell cycle at the G2/M phase and induced apoptosis.
ARCHIV DER PHARMAZIE
(2022)
Article
Chemistry, Physical
Yinli Wang, Akiho Yamauchi, Keiji Hashimoto, Tatsuya Fujiwara, Tsubasa Inokuma, Yuta Mitani, Koichi Ute, Satoru Kuwano, Yousuke Yamaoka, Kiyosei Takasu, Ken-ichi Yamada
Summary: We describe a new method of enhancing molecular recognition through substrate-additive complex formation and catalytic acylation using chiral catalyst. The study demonstrates that the additive forms a hydrogen-bonded complex with the substrate, resulting in improved reaction rate and selectivity. The synthetic applications of the resolved compounds highlight the effectiveness of this method.
Article
Chemistry, Organic
Yousuke Yamaoka, Daisuke Yamasaki, Daigo Kajiwara, Makiko Shinozaki, Ken-ichi Yamada, Kiyosei Takasu
Summary: A Zn(OTf)(2)-catalyzed domino reaction was developed for the synthesis of spirocyclic indolines from enamide-ynamides in the presence of trimethylsilyl cyanide. This reaction involved the cyclization of enamide to ynamide followed by cyanide addition, resulting in the formation of spiroindolopyrrolidines with excellent diastereoselectivity.
Article
Chemistry, Physical
Aya M. Almatary, Walaa M. El Husseiny, Khalid B. Selim, Hassan M. H. Eisa
Summary: In this study, dual drugs were developed that can inhibit carbonic anhydrase enzyme (CA) by containing sulfonamide group, and increase the sensitivity of hypoxic tumors to radio and chemotherapies by incorporating 5-nitroimidazole scaffold. The synthesized compounds demonstrated high cytotoxic activity against multiple cancer cell lines and enhanced the lethal effect of gamma-irradiation. Molecular docking and molecular dynamics simulation were performed to understand the inhibitory effect and stability of interaction.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Organic
Ken-ichi Yamada, Akiho Yamauchi, Tatsuya Fujiwara, Keiji Hashimoto, Yinli Wang, Satoru Kuwano, Tsubasa Inokuma
Summary: The effect of N-substituent on the performance of chiral N-heterocyclic carbene-catalyzed kinetic resolution using alpha-hydroxyamides was investigated. N-tert-Butyl-alpha-hydroxyamides exhibited the best performance and achieved enantioselective acylation with alpha-bromo aldehyde through chiral N-heterocyclic carbene/carboxylate anion co-catalysis, leading to a high selectivity factor up to 128.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Kenji Matsumoto, Rina Nakano, Ken-ichi Yamada, Tsukasa Hirokane, Masahiro Yoshida
Summary: This study reports an efficient platform for the one-step construction of nitrogen-containing polycyclic frameworks using a heterogeneous platinum-catalyzed oxidative alpha,beta-C(sp(3))-H dual functionalization of saturated cyclic amines. By conducting a tandem oxidative dehydrogenation/hetero Diels-Alder reaction under mild aerobic conditions, tetracyclic octahydro-dipyrroloquinoline frameworks were synthesized in good yields. The reaction was successfully applied to the one-step synthesis of natural products incargranine B aglycone and seneciobipyrrolidine. This study provides an efficient and rapid approach to nitrogen-containing fused tetracyclic compounds in a highly atom-economical manner.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Tsubasa Inokuma, Kana Masui, Koki Fukuhara, Yamada Ken-ichi
Summary: In this study, N-2-nitrophenylsulfenyl imino dipeptides bearing various functional groups were successfully synthesized and then subjected to diastereoselective indolylation. Each diastereomer of the adduct was selectively obtained using the appropriate chiral phosphoric acid catalysts. These transformations are valuable for synthesizing peptide-based drug candidates containing non-canonical amino acids.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Tsubasa Inokuma, Ken-ichi Yamada
Summary: Our recent efforts focused on the development of N-Heterocyclic carbene (NHC)-catalyzed asymmetric reactions. We observed the significant effects of remote substitution at the carbene carbon of NHCs in acylation reactions and a significant enhancement of enantioselectivity by the addition of carboxylate anions. By applying this concept, we achieved excellent enantioselectivities in kinetic resolutions of cyclic and acyclic alcohols. The effects of remote substitution were also observed in intramolecular Stetter reaction and intermolecular benzoin reaction.
Article
Chemistry, Multidisciplinary
Tsubasa Inokuma, Kentaro Hashimoto, Tatsuya Fujiwara, Chunzhao Sun, Satoru Kuwano, Ken-ichi Yamada
Summary: The remote electronic effect of a chiral aminoindanol-derived N-heterocyclic carbene catalyst on an asymmetric benzoin reaction was investigated. The catalyst containing remote electron-withdrawing substituents increased the enantioselectivity of the reaction, albeit at the expense of the reaction rate. DFT calculations provided a rationale for the enhanced enantioselectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Yousuke Yamaoka, Nao Takeuchi, Ken-ichi Yamada, Kiyosei Takasu
Summary: A Bronsted acid-catalysed cyclization of ene-ynamides has been developed for the synthesis of 7- or 8-membered azacycles in good to high yields. This method utilizes a simple C=C double bond as a nucleophile to form medium-sized rings from acyclic ynamides. The reaction conditions are mild and do not require the use of metal catalysts or high dilution for medium-sized ring formation. Various substituents, including alkyl, aryl, acetylene, and silyloxy groups, can be accommodated in this reaction system.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Tsubasa Inokuma, Kohei Iritani, Yuki Takahara, Chunzhao Sun, Yousuke Yamaoka, Satoru Kuwano, Ken-ichi Yamada
Summary: The remote electronic effects of chiral N-heterocyclic carbene catalysts on the asymmetric intramolecular Stetter reaction were investigated. The reaction rate and enantioselectivity were significantly affected by a substituent at a remote position of the catalyst. The absolute configurations of the products were revised based on X-ray diffraction. Density-functional theory calculations provided a rationalization for the improved enantioselectivity using an electron-deficient catalyst.
CHEMICAL COMMUNICATIONS
(2023)
Article
Biochemistry & Molecular Biology
Salma Fares, Khalid B. Selim, Fatma E. Goda, Magda A. A. El-Sayed, Nawaf A. AlSaif, Mohamed M. Hefnawy, Alaa A. -M. Abdel-Aziz, Adel S. El-Azab
Summary: The newly synthesized cyanobenzofuran derivatives showed broad-spectrum activity against liver cancer, colon cancer, and breast cancer cell lines. Some derivatives also displayed significant EGFR TK inhibitory activity, inducing apoptosis and cell cycle arrest.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
