Article
Chemistry, Multidisciplinary
Guoxue He, Jinyu Ma, Jianhui Zhou, Chunpu Li, Hong Liu, Yu Zhou
Summary: A new method for synthesizing indanones using L-proline as a catalyst under metal- and additive-free conditions has been developed, providing a more environmentally friendly pathway with good yields. This method can be used to synthesize the anti-AD drug donepezil.
Article
Chemistry, Multidisciplinary
Christoph Etling, Giada Tedesco, Markus Kalesse
Summary: This study investigated the different reactivity of trienones under Lewis and Bronsted acids catalysis, resulting in novel Nazarov cyclization tandem reactions terminating oxyallyl cations by ene-type reactions. The bicyclic spiro compounds produced were shown to be useful intermediates for further functionalization. Furthermore, the tandem Nazarov/ene cyclization was found to be preferred over a Nazarov/[3+2] tandem reaction for all substrates, regardless of chain length.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Multidisciplinary Sciences
Bo Yang, Shi-Jun Li, Yongdong Wang, Yu Lan, Shifa Zhu
Summary: Hydrogen atom transfer is an effective strategy for activating C-H bonds and further functionalization. Introducing water as both a hydrogen source and HRS enables internal hydrogen radical transfer, providing a breakthrough in hydrogen radical transfer for challenging processes in organic synthesis.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Siqi Dong, Shaofeng Xu, Yashi Zou, Zhaodi Li, Kai Xu, Daxu Fu, Delong Liu, Wanbin Zhang
Summary: A RuPHOX/Pd catalyzed asymmetric allylic substitution cascade of α-carbonylamides with an allylic meso-dicarbonate has been developed to synthesize chiral 3-acyl bicyclolactams bearing three vicinal carbon stereocenters in high yields. The products exhibited excellent enantioselectivity with up to 99% ee and high diastereoselectivity with >20:1 dr. Mechanistic studies revealed a dynamic kinetic resolution process during the second step of the cascade reaction, which contributed to the high diastereoselectivity. The protocol can be scaled up and the resulting products are versatile for further transformations, especially in the synthesis of natural products.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Shaofeng Li, Hanyu Nie, Mengyan Duan, Wenfei Wang, Congjun Zhu, Chuanjun Song
Summary: This work presents a strategy for the one-pot synthesis of protoberberine alkaloid derivatives using palladium catalyzed cascade alpha-arylation and cyclization, resulting in moderate to excellent isolated yields. The protocol provides an efficient and convenient path to multisubstituted protoberberine derivatives and can directly yield natural alkaloids.
Article
Chemistry, Organic
Bilge Banu Yagci, Selin Ezgi Donmez, Onur Sahin, Yunus Emre Turkmen
Summary: We have developed a catalytic aza-Nazarov reaction to synthesize substituted alpha-methylene-gamma-lactam heterocycles. The reaction can be effectively conducted using AgOTf or hydrogen-bond donors as catalysts. Both cyclic and acyclic imines can be used as starting materials, resulting in high yields and diastereoselectivities. Mechanistic studies have been performed to understand the reaction details.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Alvaro Velasco-Rubio, Rodrigo Bernardez, Jesus A. Varela, Carlos Saa
Summary: Benzofused seven-membered heterocycles such as 1,4-BZDs and 1,4-BZOs were efficiently synthesized by Rh-catalyzed hydrofunctionalization of internal alkynes and allenes in good to excellent yields. Enantioselective hydroamination of (aminomethyl)anilines yielded 3-vinyl-1,4-BZDs with excellent enantioselectivities, and orthogonal N-deprotection of 1,4-BZDs allowed for the easy entry to an advanced pyrrolobenzodiazepine metabolite of the V2-receptor antagonist Lixivaptan.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Maxime Hourtoule, Laurence Miesch
Summary: We developed a domino reaction for the synthesis of 2-amido-5-fluoropyrroles from CF3-substituted N-allenamides. By employing silver catalysis with a primary amine, the in situ generated gem-difluorinated ene-ynamides derived from CF3-substituted N-allenamides undergo simultaneous hydroamination and 5-endo-trig addition/beta-fluoride elimination sequence, leading to the construction of 2-amido-5-fluoropyrroles. This method shows excellent functional group compatibility and can be used for the synthesis of functionalized benzo-oxazoles by using 2-aminophenols.
Article
Chemistry, Organic
Jinyuan Wang, Yunzhi Liu, Nan Han, Yuan Gao, Jun Luo
Summary: A novel synthetic strategy for indanones was developed through a Pd-catalyzed direct annulation of benzaldehydes with norbornenes assisted by anilines as monodentate transient directing groups. The reaction exhibited broad functional group compatibility and high atom economy.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Takahito Kuribara, Ayahito Kaneki, Yuma Mihara, Honoka Yuba, Tetsuhiro Nemoto
Summary: In this study, we describe a scandium-catalyzed regioselective synthesis of 5-carbonyl-4-hydroxybenzofurans via a phenol-directed intramolecular Friedel-Crafts reaction. This method was successfully applied for the total synthesis of furanoflavones. Experimental and theoretical calculations suggest that hydrogen bond interactions between the phenolic hydroxy group and the scandium complex enable regioselective intramolecular cyclization.
Article
Chemistry, Organic
Mina C. Nakhla, Christopher D. Cook, John L. Wood
Summary: This manuscript discusses progress in the total synthesis of (+/-)-isopalhinine A, focusing on an allene ether Nazarov cyclization reaction to generate the bicyclic core.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Siyang Xing, Yuhan Wang, Changkun Jin, Shaochen Shi, Yihui Zhang, Ziya Liao, Kui Wang, Bolin Zhu
Summary: In this study, a method for intramolecular formal [3+2] cycloaddition of activated aziridines and epoxides with electron-deficient alkene was developed, enabling efficient construction of bridged aza- and oxa-[n.2.1] skeletons. This strategy proved to be highly efficient with the assistance of lithium iodide.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Jiang-Fei Li, Wei-Wei Xu, Rong-Hua Wang, Yue Li, Ge Yin, Mengchun Ye
Summary: The study demonstrates a novel approach for the direct construction of 7-membered rings via Ni-Al co-catalyzed unreactive C-H cyclization of benzoimidazoles with alkenes, yielding a series of tricyclic imidazoles. Transition metal-catalyzed C-H cyclization for medium-ring synthesis has been limited to reactive C-H bonds, presenting a challenge for activating unreactive C-H bonds.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Yi-Chen Liu, Pu Chen, Xue-Jiao Li, Bi-Quan Xiong, Yu Liu, Ke-Wen Tang, Peng-Fei Huang
Summary: Heterocyclic compounds, especially oxygen-containing heterocyclic compounds, play a crucial role in bioactive compounds and drug leads. This study presents a visible-light-induced dual acylation reaction of alkenes to construct 3-substituted chroman-4-ones, which involves a nitrogen-centered radical strategy for a radical tandem cyclization reaction through carbon-carbon bond cleavage of oxime esters. A series of 3-substituted chroman-4-ones were successfully prepared with high yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jin-Lin Wan, Jian-Feng Cui, Wei-Qiang Zhong, Jing-Mei Huang
Summary: In this study, iminyl radicals were generated through the electrochemical decarboxylation of alpha-imino-oxy acids using nBu(4)NBr as a mediator under exogenous-oxidant- and metal-free conditions. These iminyl radicals underwent intramolecular cyclization smoothly with adjacent (hetero)arenes to form a series of indole-fused polycyclic compounds.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Applied
Yi-Ting Wang, Yi-Lun Shih, Yen-Ku Wu, Ilhyong Ryu
Summary: Site-selective C(sp(3))-H alkenylation was achieved under photo-irradiation in the presence of a catalytic decatungstate anion. The reaction successfully combines radical addition/beta-scission sequence with photocatalytic C(sp(3))-H functionalization. The decatungstate anion participates in a chain-repairing step in reactions with weaker C-H bonds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Chieh-Yu Chang, Chun-Jen Chen, Sheng-Hao Huang, Shih-Chieh Kao, Yen-Ku Wu
Summary: A concise route to (+/-)-taiwaniaquinol B is described, in which the 6-5-6-fused ring system is constructed by sequencing a Fries rearrangement and a photo-Nazarov cyclization. The use of photoirradiation conditions is found to be crucial for promoting the key electrocyclization and mitigating the competing oxo-Michael pathway.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Pharmacology & Pharmacy
Richard Yuen, Frederick G. West, Frank Wuest
Summary: Combining PET and fluorescence imaging techniques can optimize the treatment outcomes for tumor patients. This review discusses the recent research on integrating these two imaging capabilities into one.
Article
Chemistry, Multidisciplinary
Yi-Lun Shih, Sheng-Hao Huang, Yen-Ku Wu, Ilhyong Ryu
Summary: Photocatalytic C(sp(3))-H allylation, alkynylation, and imination using unsaturated benzenesulfonyl compounds were investigated with decatungstate W10O324- as the photocatalyst. In all these reactions, selective cleavage of C(sp(3))-H bonds was achieved and combined with the radical addition/ss-scission sequence.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2022)
Article
Chemistry, Multidisciplinary
Xin-Jie Lin, Shih-Peng Huang, Min-Jie Huang, Chien-Lung Wang, Chi-How Peng, Hsueh-Ju Liu, Yen-Ku Wu
Summary: This article describes our efforts in establishing a practical and sustainable synthesis of bis(2-hydroxy-3,5-di-t-butylphenyl)methanone. We found that the phenol-aldehyde condensation reaction can be efficiently catalyzed by sulfonic acid-functionalized microporous carbon spheres (MCS-SO3H). Additionally, we developed practical and sustainable procedures for the synthesis of the title ligand by using readily available reagents instead of toxic chromium trioxide and fuming boron tribromide.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Yi-Lun Shih, Yen-Ku Wu, Mamoru Hyodo, Ilhyong Ryu
Summary: A catalytic amount of decatungstate photocatalyst under black light irradiation was able to promote the oxidative cleavage of C=C bonds with molecular oxygen, resulting in the formation of both aromatic and aliphatic ketones. The use of a high-power ultraviolet light-emitting diode at 365 nm for the continuous flow reaction of alpha-methylstyrene significantly reduced the reaction time.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Amanda J. Boyle, Emily Murrell, Junchao Tong, Christin Schifani, Andrea Narvaez, Melinda Wuest, Frederick West, Frank Wuest, Neil Vasdev
Summary: This study demonstrates the potential of using fluorine-18 labeled 6-fluoro-6-deoxy-D-fructose (6-[F-18]FDF) as a PET radiotracer to image microglial GLUT5 density in the brain following neuroinflammatory insult. The uptake of 6-[F-18]FDF in the ipsilateral striatum of LPS-injected rats was significantly higher compared to the contralateral striatum, while [F-18]FDG showed highest uptake at one week post-LPS injection. Immunohistochemistry confirmed the activation of microglia and astrocytes in the ipsilateral striatum. This proof-of-concept study highlights the early response of 6-[F-18]FDF to neuroinflammatory stimuli and its potential applications in neuroinflammatory and neurodegenerative diseases.
Article
Chemistry, Organic
Christian. L. Jankovic, F. G. West
Summary: Oxygenated-1,2-cyclohexadienes and their unsubstituted counterpart can be generated by fluoride-induced desilylation and undergo cycloaddition reactions with a variety of alkene traps, forming bicyclo[4.2.0]octenes. The reaction shows good regioselectivity and modest diastereoselectivity.
Article
Pharmacology & Pharmacy
Nolan Jackson, Abdulaziz Alhussan, Kyle Bromma, David Jay, James C. C. Donnelly, Frederick G. G. West, Afsaneh Lavasanifar, Michael Weinfeld, Wayne Beckham, Devika B. B. Chithrani
Summary: This study aimed to explore the use of an antimalarial drug, PYD, as a DNA repair inhibitor to enhance the DNA damage induced by RT/GNP treatment. The results showed that PYD could significantly increase DNA double-strand breaks and inhibit cell proliferation in cancer cell lines. These promising findings could lay the foundation for the clinical application of this treatment modality.
Article
Chemistry, Multidisciplinary
Christian L. L. Jankovic, Kyle C. C. McIntosh, Verner A. A. Lofstrand, F. G. West
Summary: Mild fluoride-mediated desilylative conditions generate 1,2-cyclohexadienes, which undergo efficient intramolecular [2+2] trapping to form tricyclic alkylidene cyclobutanes with complete diastereoselectivity for the cis-fused products. These cyclohexadienes can be trapped by pendent styrenes or electron-deficient olefins, and 14 substrates have been disclosed. The reactions achieve yields up to 91% at ambient temperature using only cesium fluoride and the necessary precursors are easily accessible from substituted 2-bromocyclohexenones.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Chen-Yang Tsai, Yin-Jia Jhang, Yen-Ku Wu, Ilhyong Ryu
Summary: This study reports a protocol for alkene hydroxyalkenylation and a photocatalytic protocol for alkoxyalkenylation. Alkenes can be converted into the corresponding 1-phenylsulfonyl-4-hydroxyalkenes or alkoxyalkenes in good to high yields using a persulfate anion as an oxidation reagent and 1,2-bis(phenylsulfonyl)ethylene as a radical acceptor. The methods exhibit wide substrate adaptability and regioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Multidisciplinary Sciences
Yasser Tabana, Chih-Hsuan Lin, Dinesh Babu, Ramanaguru Siva-Piragasam, Ashley A. Ponich, Tae Chul Moon, Arno G. Siraki, Shokrollah Elahi, Richard Fahlman, Frederick G. West, Khaled Barakat
Summary: This study presents a method for identifying the cellular targets of Compound A in human peripheral blood mononuclear cells (PBMCs). By synthesizing a probe based on the chemical structure of Compound A and demonstrating its efficient binding to bovine serum albumin, this method can be used to further identify potential protein targets of small molecules in living cells. These findings provide a valuable starting point for exploring the molecular mechanisms underlying the immunomodulatory effects of Compound A.
Article
Biochemistry & Molecular Biology
Natasha Rana, Marwa A. A. Aziz, Rabah A. T. Serya, Deena S. S. Lasheen, Nermin Samir, Frank Wuest, Khaled A. M. Abouzid, F. G. West
Summary: Rapid cell division and reprogramming of energy metabolism are crucial characteristics of cancer cells. In breast cancer, fructose can substitute glucose as an alternative energy source. GLUT5, the fructose transporter, is overexpressed in breast cancer cells, making it a valuable target for cancer detection and selective targeting of drugs. A novel fluorescence assay was used to screen and identify highly potent C-3 modified compounds as d-fructose analogues, providing avenues for the development of more potent probes targeting GLUT5-expressing cancer cells.
ACS BIO & MED CHEM AU
(2022)
Article
Chemistry, Organic
Zih-Siang Hong, Shih-Chieh Kao, Yu-Tsen Cheng, Chun-Jen Chen, Yen-Ku Wu
Summary: In this study, a photoflow method was developed for the radical-based coupling of unactivated arenes and aryl chlorides. The reaction proceeded smoothly at ambient temperature without the need for metal catalysts. Importantly, the reaction conditions were optimized for chloroarenes with different electronic properties. Despite the generally lower reactivity of aryl chlorides compared to their iodide and bromide counterparts, the developed protocol efficiently converted readily available and inexpensive chloroarenes into unsymmetrical biaryl products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Wan-Ling Peng, Yin-Jia Jhang, Chieh-Yu Chang, Po-Kai Peng, Wei-Ting Zhao, Yen-Ku Wu
Summary: A total synthesis of racemic mersicarpine from diethyl 4-oxopimelate is described, utilizing a 2-indolyl radical cyclization to construct the pyrido[1,2-a]indole scaffold with an all-carbon quaternary stereocenter.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
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)
