Article
Chemistry, Organic
Yusuke Tomita, Naoto Haraguchi, Sayori Kiyota, Nobuyuki Komine, Masafumi Hirano
Summary: A traditional cobalt catalyst system has been found to exhibit previously undiscovered reactivity. Depending on the choice of tertiary phosphines and substrates, this catalytic system can catalyze diverse cycloadditions, yielding various cyclic compounds. The bite angles of the ligands used significantly contribute to the catalytic diversity.
Article
Chemistry, Organic
Fang-Fang Feng, Jun-An Ma, Dominique Cahard
Summary: The research successfully synthesized valuable pentafluorosulfanyl compounds through the radical 1,5-chloropentafluorosulfanylation of vinyl cyclopropanes initiated by Et3B/O-2, with further transformation of the C=C bond accomplished, demonstrating the utility of this reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Sajan Pradhan, Fahimeh Mohammadi, Jean Bouffard
Summary: In this study, we demonstrated the exceptional ability of 1,3-diaza-2-azoniaallene cations to undergo formal (3+2) cycloadditions with unactivated benzene derivatives below room temperature, yielding thermally stable dearomatized adducts on a multi-gram scale. The cycloaddition process tolerates polar functional groups, activating the ring for further elaboration. Additionally, when treated with dienophiles, the cycloadducts undergo a cascade reaction, resulting in substituted or fused arenes, including naphthalene derivatives. This two-step sequence offers an unconventional approach for the synthesis of ubiquitous aromatic building blocks and has demonstrated applications in the preparation of substituted acenes, isotopically labeled molecules, and medicinally relevant compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Mikhail Feofanov, Dmitry Sharapa, Vladimir Akhmetov
Summary: This study reveals the alumina-mediated propargylic C-H activation, which converts common alkynes into valuable compounds under mild conditions. The partial hydroxylation of alumina's surface is demonstrated to play a crucial role in this reaction through theoretical investigation and experimental observations.
Article
Chemistry, Multidisciplinary
Qun Zhao, Yao Li, Qing-Xia Zhang, Jin-Pei Cheng, Xin Li
Summary: The highly enantioselective aza-Diels-Alder reaction of 2-aryl-3H-indol-3-ones with unactivated dienes using a B(C6F5)(3)/chiral phosphoric acid catalyst system under mild conditions offers rapid access to a broad scope of tetrahydropyridine derivatives with excellent outcomes. The reaction is efficient, with maintained enantioselectivity even at lower catalyst loadings of 0.1 mol %. DFT calculations provide convincing evidence for the interpretation of stereoselection.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Sandor Balazs Kiraly, Attila Benyei, Erika Lisztes, Tamas Biro, Balazs Istvan Toth, Tibor Kurtan
Summary: The study synthesized 5,6-dihydro-2H-pyran derivatives containing an o-formylaryl amine or ether moiety through diastereoselective domino-Knoevenagel-IMHDA reactions. Depending on different competing pathways, novel spiro heterocyclic products with a tetrahydroquinoline or chroman unit were formed. These products showed low micromolar IC50 values against A2780 and WM35 human cancer cell lines.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Lewis B. B. Smith, Roly J. J. Armstrong, Jingyan Hou, Edward Smith, Ming Sze, Alistair J. J. Sterling, Alex Smith, Fernanda Duarte, Timothy J. J. Donohoe
Summary: An efficient method for synthesizing cyclohexenes from readily available tetrahydropyrans has been developed via a tandem 1,5-hydride shift-aldol condensation. Aluminium reagents, such as Al2O3 or Al((OBu)-Bu-t)(3), were found to be crucial for promoting the 1,5-hydride shift with complete regio- and enantiospecificity. The mild reaction conditions and the availability of various methods to access the tetrahydropyran starting materials make this method versatile and tolerant to different functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Lei Yu, Wenhai Li, Anyawan Tapdara, Sara Helen Kyne, Mandeep Harode, Rasool Babaahmadi, Alireza Ariafard, Philip Wai Hong Chan
Summary: An efficient chiral gold(I) complex-catalyzed synthetic method for the regio- and enantioselective nitroso-Diels-Alder (NDA) reaction of 1,6-diyne esters with nitrosobenzenes is described. The reaction provides access to a wide range of 3,5,6,8a-tetrahydro-1H-benzo[c][1,2]oxazines as a single regioisomer with high yields and enantiomeric excess values.
Article
Chemistry, Organic
Quan Tran, Arkajyoti Sengupta, K. N. Houk
Summary: The 1,5-sigmatropic hydrogen shift in cyclopentadiene is traditionally believed to be a unimolecular pericyclic reaction, but Yamabe proposed a more complex bimolecular mechanism. Recent computational studies show that the unimolecular mechanism is kinetically more favorable and closer to experimental values compared to the bimolecular mechanism proposed by Yamabe.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Yu Zheng, Shencheng Qian, Pengcheng Xu, Tianting Ma, Shenlin Huang
Summary: A method for synthesizing fused dihydropyran isoxazole derivatives has been developed through an intermolecular inverse-electron-demand Diels-Alder reaction using readily available alkylidene isoxazol-5-ones and unactivated alkenes. This reaction is promoted by inexpensive and commercially available BF3·Et2O catalyst without the need for metal Lewis acids. The cycloaddition transformation can proceed under mild conditions and has a broad substrate scope, providing a variety of bicyclic 5,6-dihydro-4H-pyrano[3,2-d]isoxazoles.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Erandi Liyanage Perera, Daesung Lee
Summary: In this study, a sequential inter- and intramolecular addition reaction on electron-deficient 1,3-diynes conjugated with a ketone, ester, or imide functionality is described. This process is effectively directed by a propargylic -OH or -NH functionality. Alcohols, amines, and thiols show excellent reactivity for the initial addition. The addition of amines occurs at ambient temperature, whereas other nucleophiles require high temperatures and a base additive.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Li Pang, Shu-Jun Fang, Pei-Sen Zou, Wang Wang, Jun-Cheng Su, Xiao-Qing Liu, Cheng-Xue Pan, Dong-Liang Mo, Gui-Fa Su
Summary: We report a transition-metal free [4 + 4] cycloaddition reaction between 2-alkynyl quinazolines and aza-ortho-quinone methides (ao-QMs) generated from 2-(bromomethyl)anilines, leading to the synthesis of various [1,5]diazocino[2,1-b]quinazolinones in good to excellent yields under mild reaction conditions and short reaction time. Furthermore, a [1,5]diazocino[2,1-b]quinazolinone derived from estrone was easily prepared in 30% total yield over five steps, and showed significant inhibition of nitric oxide generation in LPS-stimulated RAW264.7 cells. This method offers advantages such as broad substrate scope, gram-scale preparation, and simple purification operation without flash column chromatography.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Bipin Kumar Behera, Pallav Jyoti Arandhara, Bikoshita Porashar, Surjya Kumar Bora, Anil K. Saikia
Summary: A facile and efficient method for the synthesis of structurally diversified 2-pyridones using the [4 + 2] annulation of in situ generated azadienes from N-propargylamines and active methylene compounds is demonstrated. The reaction, promoted by an inorganic base, provides moderate to good yields. The developed methodology is applicable for the direct and formal synthesis of various bioactive molecules, with the synthetic utility further illustrated by late-stage functionalization of the products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Stefano Nejrotti, Francesco Marra, Emanuele Priola, Andrea Maranzana, Cristina Prandi
Summary: The reactivity of furan-ynes in combination with pyridine and quinoline N-oxides in the presence of a Au(I) catalyst has been studied, enabling the synthesis of three different heterocyclic scaffolds. Selective access to two out of the three possible products has been achieved through the fine-tuning of the reaction conditions. The reactions proceed smoothly at room temperature and open-air, and were further extended to a broad substrate scope, affording functionalized dihydropyridinones and pyranones.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Vasilissa V. Shirokova, Viktoria A. Ikonnikova, Pavel N. Solyev, Vladislav A. Lushpa, Alexander A. Korlyukov, Alexander D. Volodin, Nadezhda S. Baleeva, Mikhail S. Baranov, Andrey A. Mikhaylov
Summary: This study demonstrates the cyclization of directly accessible 8-substituted tetrahydroquinolines triggered by 1,5-hydride shift under scandium(III) triflate catalysis, yielding julolidine derivatives in 21-98% yields. The scope of the reaction, several follow-up transformations, and a significant side process discovered during optimization of the conditions are highlighted.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Min Lu, Hua Wu, Xiaoyu Zhang, Hua Wang, Yue Hu, Vicki L. Colvin, Yu Zhang, William W. Yu
Article
Chemistry, Physical
Hong-Cheng Shen, Ling Zhang, Shu-Sen Chen, Jiajie Feng, Bo-Wen Zhang, Ying Zhang, Xinhao Zhang, Yun-Dong Wu, Liu-Zhu Gong
Article
Chemistry, Physical
Min Lu, Jie Guo, Po Lu, Liu Zhang, Ying Zhang, Qilin Dai, Yue Hu, Vicki L. Colvin, William W. Yu
JOURNAL OF PHYSICAL CHEMISTRY C
(2019)
Article
Chemistry, Inorganic & Nuclear
Sheng Zhang, Wenjiao Mo, Jiangwei Zhang, Zengqi Zhang, Bing Yin, Dengwei Hu, Sanping Chen
INORGANIC CHEMISTRY
(2019)
Article
Nanoscience & Nanotechnology
Hua Wang, Xiangtong Zhang, Ning Sui, Yue Hu, Vicki L. Colvin, William W. Yu, Yu Zhang
ACS APPLIED MATERIALS & INTERFACES
(2020)
Article
Chemistry, Inorganic & Nuclear
Xiangtong Zhang, Hua Wang, Shixun Wang, Yue Hu, Xuan Liu, Zhifeng Shi, Vicki L. Colvin, Shengnian Wang, William W. Yu, Yu Zhang
INORGANIC CHEMISTRY
(2020)
Article
Chemistry, Physical
Hua Wang, Xiangtong Zhang, Ning Sui, Yue Hu, Vicki L. Colvin, Xue Bai, Yu Zhang, Andrey L. Rogach, William W. Yu
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2020)
Article
Nanoscience & Nanotechnology
Zhen Xiao, Qingbo Zhang, Xiaoting Guo, Jake Villanova, Yue Hu, Indrek Kulaots, Daniel Garcia-Rojas, Wenhua Guo, Vicki L. Colvin
ACS APPLIED MATERIALS & INTERFACES
(2020)
Article
Chemistry, Multidisciplinary
Shu-Sen Chen, Dean J. Tantillo
Article
Chemistry, Organic
Tao Zhang, Wen-Ao Li, Hong-Cheng Shen, Shu-Sen Chen, Zhi-Yong Han
Summary: An asymmetric Heck-Matsuda reaction targeting acyclic internal alkenes was successfully developed through the strategy of chiral anion phase transfer, resulting in high levels of enantioselectivity in the formation of chiral ketones. The use of a catalytic amount of dimethyl sulfoxide (DMSO) as an additive is crucial for suppressing palladium-hydride-mediated side reactions.
Article
Engineering, Biomedical
Elaina Atherton, Yue Hu, Sophie Brown, Emily Papiez, Vivian Ling, Vicki L. Colvin, David A. Borton
Summary: This study aimed to understand and mitigate the neuroinflammatory response to neural implants. By using three-dimensional primary neural cultures, the researchers successfully separated the innate and systemic immune responses and created an in vitro model of the device-tissue interface.
JOURNAL OF NEURAL ENGINEERING
(2022)
Article
Multidisciplinary Sciences
Qingbo Zhang, Yue Hu, Caitlin M. Masterson, Wonhee Jang, Zhen Xiao, Arash Bohloul, Daniel Garcia-Rojas, Hema L. Puppala, George Bennett, Vicki L. Colvin
Summary: This study characterized the dissolution process and associated biological activity of silver nanoparticles with different dimensions, shapes, and surface chemistries. A quantitative model was developed to relate material structure to silver dissolution and microbial toxicity. The results showed that shape had the most profound influence on antibacterial activity, while surface coatings had the least impact.
Article
Chemistry, Multidisciplinary
Yue Hu, Federica Rigoldi, Hui Sun, Alfonso Gautieri, Benedetto Marelli
Summary: We used molecular dynamics simulations to find new tetrapeptide sequences with pH-tunable assembly properties by screening all possible histidine-bearing sequences. These tetrapeptides have potential applications in triggering the delivery of bioactive molecules.
CHEMICAL COMMUNICATIONS
(2023)
Article
Materials Science, Biomaterials
Yue Hu, Qingbo Zhang, Daniel Garcia-Rojas, Vivian Ling, Caitlin M. Masterson, Yidan Bi, Zhen Xiao, Xiaoting Guo, Jake Villanova, Joshua Dunn, Vicki L. Colvin
Summary: The use of reactive polymeric surface coatings can increase the cerium(iii) content of ceria nanoparticles, making them remarkable antioxidants. The length and architecture of the coating polymer can be tailored to enhance the antioxidant capacity of the nanoparticles.
JOURNAL OF MATERIALS CHEMISTRY B
(2022)
Article
Chemistry, Physical
Yang-Yang Xing, Shu-Sen Chen, De-Zhan Chen, Dean J. Tantillo
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2020)
