Article
Chemistry, Organic
Yunhe Lv, Junrong Lai, Weiya Pu, Jin Wang, Wanru Han, Axue Wang, Mengyue Zhang, Xue Wang
Summary: A novel, practical, and green synthetic method is reported for the synthesis of various tetrasubstituted allenyl iodides using readily available 1,3-enynes with sulfonyl hydrazides and I2 through tert-butyl hydroperoxide (TBHP)-mediated 1,4sulfonyliodination under metal-free conditions. The proposed method exhibits a broad substrate scope, operational simplicity, tolerance to air, high functional-group tolerance, satisfactory yields, and excellent regioselectivity as well as involves the use of cost-effective reagents such as green oxidants.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Liang Zhang, Neng-Jie Mou, Dong-Rong Xiao, Xin Zhuang, Xiao-Long Lin, Tian Cai, Qun-Li Luo
Summary: Functionalized oxa-heterocycles, basic structural units in natural products and bioactive molecules, can be efficiently synthesized through iodine-mediated annulation of propargylic alcohols with cyclic 1,3-dicarbonyl compounds, leading to novel cyclic scaffolds with high regioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Hong Hou, Yingjie Pan, Yuejie Sun, Ying Han, Chaoguo Yan, Yaocheng Shi, Shaoqun Zhu
Summary: A visible-light photoredox-catalyzed regioselective 1,4-hydroalkylation of 1,3-enynes is described. Various di- and tri-substituted allenes were successfully synthesized under the current reaction conditions. The carbon nucleophile is activated by visible-light photoredox to generate its radical species, allowing addition with un-activated enynes. The synthetic utility of this protocol was demonstrated by a large-scale reaction and derivatization of the allene product.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Fu-Sheng He, Ping Bao, Feiyan Yu, Ling-Hui Zeng, Wei-Ping Deng, Jie Wu
Summary: By using CuOAc as the catalyst, a four-component reaction involving 1,3 enynes, diselenides, DABCO, (SO2)(2), and cycloketone oxime esters was successfully conducted to synthesize diverse cyanoalkylsulfonylated allenyl selenides. This reaction shows high functional group tolerance and a broad substrate scope, enabling regioselective formation of C-SO2 and C-Se bonds under mild conditions, with potential application in late-stage functionalization of drug-based molecules.
Article
Chemistry, Organic
Yunhe Lv, Wanru Han, Weiya Pu, Jinhui Xie, Axue Wang, Mengyue Zhang, Jin Wang, Junrong Lai
Summary: A novel and practical copper-catalyzed reaction for 1,4-sulfonylcyanation of 1,3-enynes under mild conditions is described. The reaction provides efficient access to a variety of 5-sulfonylpenta-2,3-dienenitrile derivatives with excellent functional group tolerance and selectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Applied
Raffaella Mancuso, Patrizio Russo, Melania Lettieri, Domenico Santandrea, Corrado Cuocci, Bartolo Gabriele
Summary: Polycyclic heterocyclic derivatives can be synthesized in one step by a carbonylative double cyclization approach, with yields ranging from 45% to 86%, showing promising potential for various applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Yunhe Lv, Jinhui Xie, Weiya Pu, Xue Wang, Huanhuan Zhang, Xuerui Li, Yan Liu, Fei Chen, Yunfeng Xu
Summary: We developed a strategy for the copper-catalyzed three-component reaction to synthesize tetrasubstituted allenes with phosphinoyl and cyano groups. The reaction exhibited high functional group compatibility and good yields under mild conditions. A preliminary reaction mechanism involving the formation of phosphinoyl radicals and their regioselective addition to 1,3-enynes was proposed.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Luciana Cicco, Filippo Maria Perna, Aurelia Falcicchio, Angela Altomare, Francesco Messa, Antonio Salomone, Vito Capriati, Paola Vitale
Summary: A metal-free and environmentally friendly approach was developed for the synthesis of important 1,2,3-triazole compounds. This method not only allows for high-yield synthesis of target products at room temperature and under aerobic conditions, but also enables the synthesis of pharmaceutically relevant triazole derivatives through a one-pot process, simplifying the synthetic steps.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Kazumasa Funabiki, Kengo Yamada, Yuta Arisawa, Arina Watanabe, Tomohiro Agou, Yasuhiro Kubota, Toshiyasu Inuzuka, Yohei Miwa, Taro Udagawa, Shoichi Kutsumizu
Summary: A series of perfluoronaphthalene-based donor-acceptor-donor fluorescent dyes were successfully synthesized using a one-step route. The perfluoronaphthalene moiety served as a good electron-accepting aromatic ring with excellent intramolecular charge transfer properties. Replacing the naphthalene ring with perfluoronaphthalene stabilized the energy levels and reduced the energy band gap, leading to a change in the emission color. Among the synthesized dyes, those with diphenylamino groups showed the highest fluorescence quantum yields in solution and film, while the dye with carbazoyl group exhibited the highest fluorescence quantum yield in the crystalline state.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Cheng Chen, Cheng-Zhuo Du, Xiao-Ye Wang
Summary: This review provides an overview of research on BN-heteroarenes, focusing on the synthesis, properties, and potential applications of 1,4-azaborine-based compounds. It highlights their value beyond multiresonant thermally activated delayed fluorescence (MR-TADF) materials and aims to stimulate collaboration between chemists and materials scientists in related fields.
Article
Chemistry, Multidisciplinary
You-Jie Yu, Michael Schaefer, Constantin G. Daniliuc, Ryan Gilmour
Summary: A catalysis-based regioselective method for the synthesis of compact, highly functionalized products from trifluoromethyl substituted 1,3-dienes has been developed. The new method allows E,Z-mixed dienes to be converted to a single E-alkene isomer and utilizes an inexpensive and convenient I(I)/I(III) catalysis platform. This method enables the synthesis of delta-fluoro-alcohol and amine derivatives in a single operation, and is compatible with various nucleophiles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
An T. Ho, Seth C. Ensign, Evan P. Vanable, David Portillo, Jenna N. Humke, Gregory D. Kortman, Kami L. Hull
Summary: The Ir-catalyzed regioselective hydroamination of allyl amines and the catalyst-controlled regiodivergent hydroamination of homoallylic amines with aniline nucleophiles have been reported. These reactions can selectively synthesize diamines at different positions, and exhibit good reaction yields.
Article
Chemistry, Multidisciplinary
Miao Bai, Shihu Jia, Jingyang Zhang, Hong-Gang Cheng, Hengjiang Cong, Shanshan Liu, Zhiqian Huang, Yaoguo Huang, Xiaoming Chen, Qianghui Zhou
Summary: This article presents a modular and convergent method for the rapid assembly of 1,3-trans-disubstituted THIQ frameworks, highlighting the broad synthetic utility of this approach in the synthesis of naphthylisoquinoline alkaloids.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Kentaro Iwaki, Kazuhiro Tanagawa, Soichiro Mori, Koki Maruno, Yuji Sumii, Osamu Nagata, Norio Shibata
Summary: In this study, we reported a metal-free hydration reaction of pyridine-SF4-alkynes under acidic conditions, which synthesized pyridine-SF4-methyl ketones with yields ranging from 59% to 93%. We further demonstrated the synthetic applications of these compounds, including chlorination, NaBH4 reduction, Baeyer-Villiger oxidation, and the generation of enol triflates. These compounds show promise as useful building blocks in the synthesis of a wide range of SF4-containing drug candidates.
Article
Chemistry, Organic
Jianwei Xie, Muhammad Suleman, Guxin Qian, Ping Lu, Yanguang Wang
Summary: A facile and efficient synthesis of novel 2-(1,2,3,4-tetrahydroisoquinolin-4-yl)-1,3-diarylpropane-1,3-diones via the Sc(OTf)3-promoted reaction is reported. The reaction involves C-H bond insertion, generation of triflic acid by-product, formation of diazonium intermediate, and intermolecular nucleophilic substitution step.
Article
Chemistry, Multidisciplinary
Takashi Ikawa, Shigeaki Masuda, Shuji Akai
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
Takashi Ikawa, JingKai Sun, Akira Takagi, Shuji Akai
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Correction
Chemistry, Organic
Takashi Ikawa, JingKai Sun, Akira Takagi, Shuji Akai
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Akira Takagi, Kazuki Usuguchi, Ippei Takashima, Kensuke Okuda
Summary: The antiausterity natural product (+/-)-uvaridacol L was synthesized for the first time in seven steps from myo-inositol. The preferential cytotoxicity of racemic uvaridacol L against cancer cell lines able to adapt to nutrient deprivation was also evaluated under nutrient deprived conditions. Additionally, morphological evaluation was carried out.
Article
Chemistry, Multidisciplinary
Takashi Ikawa, Yuta Yamamoto, Akito Heguri, Yutaka Fukumoto, Tomonari Murakami, Akira Takagi, Yuto Masuda, Kenzo Yahata, Hiroshi Aoyama, Yasuteru Shigeta, Hiroaki Tokiwa, Shuji Akai
Summary: In recent years, it has been discovered that London dispersion interactions play an important role in controlling the regio- and stereo-selectivity of reactions. These interactions are dominant in selective catalysis, while repulsive steric interactions are predominant in noncatalytic reactions. A novel method utilizing London dispersion interactions has been developed for the synthesis of proximal biphenylenes, which have potential applications in ligands, catalysts, and medicines.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Shuhei Hori, Sho Ishida, Go Itoh, Koji Sugiyama, Chiharu Yuki, Masahiro Egi, Kenzo Yahata, Takashi Ikawa, Shuji Akai
Summary: 4,5,6,7-Tetrahydroisobenzofurans, corresponding to the AC(D)E ring structure of viridin with required substituents on the A-ring, were synthesized via Diels-Alder adduct of a furan derivative and maleic anhydride with high regio- and stereoselectivities. Key steps in this synthesis included regioselective ring opening, stereoselective epoxidation, and AlMe3-mediated regioselective epoxide opening followed by stereoselective C-methylation.
Article
Chemistry, Multidisciplinary
Tsuyoshi Yamada, Akiko Fujii, Kwihwan Park, Chikara Furugen, Akira Takagi, Takashi Ikawa, Hironao Sajiki
Summary: An intramolecular cyclization reaction using alkynyl cyclic acetals as substrates and silver triflate or boron trifluoride etherate as catalysts has been developed for the synthesis of various phenanthrene derivatives. The reaction mechanism involves either alkyne activation or acetal activation pathways based on pi- or sigma-Lewis acidities, as suggested by the X-ray structure analysis and computational density functional theory study.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2022)
Article
Chemistry, Organic
Naoki Oka, Tsuyoshi Yamada, Hironao Sajiki, Shuji Akai, Takashi Ikawa
Summary: A wide range of aryl boronic esters were synthesized and easily purified, showing higher yields in Suzuki-Miyaura couplings compared to aryl boronic acids or pinacol esters.
Article
Chemistry, Organic
Kwihwan Park, Shinichi Furusato, Chikara Furugen, Takashi Ikawa, Tsuyoshi Yamada, Hironao Sajiki
Summary: In this study, a solvent-free ruthenium-on-carbon-catalyzed hydrogenation reaction of CBDK was developed for the production of cis-CBDO, and the reaction mechanism for cis-selectivity was proposed based on density functional theory (DFT) calculations.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Satoshi Horino, Tomoya Nishio, Shinji Kawanishi, Shinya Oki, Koichi Nishihara, Takashi Ikawa, Kyohei Kanomata, Karla Wagner, Harald Groeger, Shuji Akai
Summary: In this study, a method for obtaining S enantiomers from secondary 3-(trialkylsilyl)propargyl alcohols was achieved by using a well-known R-selective Pseudomonas fluorescens lipase in combination with a racemization catalyst VMPS4, in which the silyl group reverses the size relationship of substituents near the carbinol moiety. Immobilization of the lipase on Celite was found to be important for achieving a high efficiency of the dynamic kinetic resolution.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Nutrition & Dietetics
Kensuke Okuda, Ippei Takashima, Akira Takagi
Summary: The behavior of essential trace metal elements in living organisms has attracted increasing attention due to their regulation by metallothionines, transporters, etc. Non-invasive methods using small molecule fluorescent probes have been developed to determine their cellular functions, focusing on zinc and monovalent copper. Recognition-based probes are hindered by intracellular chelators, while reaction-based probes release fluorophores triggered by zinc or copper, enabling the detection of low concentrations of such metals.
JOURNAL OF CLINICAL BIOCHEMISTRY AND NUTRITION
(2023)
Article
Chemistry, Medicinal
Akira Takagi, Kazuki Usuguchi, Ippei Takashima, Kensuke Okuda
Summary: Nutrient starvation in cancer-specific environments contributes to cancer cell resistance to chemotherapy and malignancy development. Our newly synthesized glucose derivative, beta-1,3,6-O-tribenzoyl-D-glucose (3), exhibits preferential cytotoxicity towards pancreatic and colon cancer cells in low nutritional environments. The extent of ester functionalization in compound 3 plays an important role. Fluorescence imaging confirms that compound 3 induces cell death in nutrient-deprived conditions. This study highlights the potential of chemically modified glucose in developing compounds to treat refractory cancers.
CHEMICAL & PHARMACEUTICAL BULLETIN
(2023)
Article
Chemistry, Organic
Kwihwan Park, Naoki Oka, Yoshinari Sawama, Takashi Ikawa, Tsuyoshi Yamada, Hironao Sajiki
Summary: We developed a platinum-catalyzed deuteration reaction using deuterium oxide as a deuterium source, which selectively deuterated tert-allylic alcohols with good deuterium content. The obtained deuterium-labeled allylic alcohols were further transformed into various deuterium-labeled building blocks without degradation of the original deuterium content.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Alexander M. Prophet, Kritanjan Polley, Gary J. Van Berkel, David T. Limmer, Kevin R. Wilson
Summary: The oxidation kinetics of iodide by ozone at the air-water interface is studied in single microdroplets. Molecular simulations and kinetic modeling are used to understand the underlying multiphase mechanism.
Article
Chemistry, Multidisciplinary
Rong Zhang, Jiajing Lan, Fei Wang, Shumei Chen, Jian Zhang
Summary: By utilizing 1,1'-ferrocene dicarboxylic acid as a chelating and surface protection ligand, we have synthesized multi-nuclear indium oxide clusters with varying nuclear sizes, including heptanuclear and thirteen-nuclear clusters. These clusters possess labile coordination sites, allowing for structural modification and self-assembly, resulting in the formation of various cluster structures.
Article
Chemistry, Multidisciplinary
Hui Wang, Hui Liu, Mingsen Wang, Jiaheng Hou, Yongjun Li, Yuancheng Wang, Yingjie Zhao
Summary: Two supramolecular complexes were prepared using CBs and M1, and their single-crystal structures were analyzed by SCXRD. The unexpected 1:2 self-assembly structure between M1 and CB[8] was discovered for the first time. These complexes exhibit unique photophysical properties and provide valuable information about the structure and photophysical properties of supramolecular complexes.
Article
Chemistry, Multidisciplinary
Chang-Hee Lee, Sookil Park, Sanggil Kim, Ji Young Hyun, Hyun Soo Lee, Injae Shin
Summary: The epidermal growth factor receptor (EGFR) is a cell-surface glycoprotein involved in cell proliferation and tumor development. This study used a fluorescently labeled EGFR to investigate its time-dependent endocytosis in live cells and found that appended glycans affect EGFR internalization. Additionally, the study detected sialic acid residues attached to EGFR on the live cell surface using FRET-based imaging. This research provides valuable insights into the cellular functions of EGFR.
Article
Chemistry, Multidisciplinary
Subhankar Sahu, Lokesh Kumar, Sumita Das, Dipti Gupta, Ruchi Anand
Summary: This study proposes a strategy that combines organic electronics with biosensor scaffolds to create a compact device for monitoring environmental aromatic pollution. By coupling biosensing protein MopR with an organic electrochemical transistor (OECT), a sensor module capable of efficient detection of phenol was designed. Exclusive phenol detection with minimal loss of sensitivity could be achieved in complex pollutant mixtures and real environmental samples.
Review
Chemistry, Multidisciplinary
Changseok Lee, Hyung-Joon Kang, Sungwoo Hong
Summary: The formation of C-N bonds through hydroamination reactions catalyzed by nickel hydrides has been a topic of recent interest. This approach offers a way to efficiently transform a variety of alkene and alkyne substrates into compounds enriched with C-N bonds. The review provides a concise overview of the underlying reaction mechanisms and aims to stimulate further progress in NiH-catalytic techniques and catalyst design.
Article
Chemistry, Multidisciplinary
Yueci Wu, Lu-Lu Sun, Hai-Hao Han, Xiao-Peng He, Weiguo Cao, Tony D. James
Summary: Drug-induced liver injury (DILI) is a common cause of acute liver failure in the USA and Europe, but most cases can be recovered or prevented by discontinuing the offending drug. Recent research has found that peroxynitrite (ONOO-) can be used as a potential indicator for early diagnosis of DILI, and there is an urgent need to establish a method to detect and track peroxynitrite in DILI cases. In this study, a FRET-based nano fluorescent probe CD-N-I was developed, which showed high selectivity and sensitivity in detecting peroxynitrite. The probe successfully detected exogenous peroxynitrite in live cells and endogenous peroxynitrite in APAP-induced liver injury of HepG2 cells.
Article
Chemistry, Multidisciplinary
Dmitry L. Lipilin, Mikhail O. Zubkov, Mikhail D. Kosobokov, Alexander D. Dilman
Summary: This article describes a direct photocatalytic method for the thiolation of unprotected acids, which was previously challenging. By using a thionocarbonate reagent with an N-O bond, the efficient conversion of carboxylic acids to thiols is achieved.
Article
Chemistry, Multidisciplinary
Jason Malenfant, Lucille Kuster, Yohann Gagne, Kouassi Signo, Maxime Denis, Sylvain Canesi, Mathieu Frenette
Summary: Raman microscopy can reveal compound-specific vibrational fingerprints without sample preparation. The combination of efficient theoretical calculations and a user-friendly software can accurately predict peak positions and provide match scores to assist with structure determination.
Article
Chemistry, Multidisciplinary
Jayoh A. Hernandez, Paul S. Micus, Sean Alec Lois Sunga, Luca Mazzei, Stefano Ciurli, Gabriele Meloni
Summary: Essential trace metals play crucial roles in the survival and virulence of bacterial pathogens. Helicobacter pylori requires nickel for colonization and persistence in the stomach, and NixA is an essential nickel transporter in this process. This study characterizes the selectivity and electrogenic nature of NixA-mediated nickel transport.
Article
Chemistry, Multidisciplinary
Tarali Devi, Kuheli Dutta, Jennifer Deutscher, Stefan Mebs, Uwe Kuhlmann, Michael Haumann, Beatrice Cula, Holger Dau, Peter Hildebrandt, Kallol Ray
Summary: This study emphasizes the importance of subtle electronic changes and secondary interactions in the stability of biologically relevant metal-dioxygen intermediates. It also shows that the role of the chloride ligand in stabilizing the Fe-III-(OOBu)-Bu-t moiety can extend to other anions, including the thiolate ligand.
Article
Chemistry, Multidisciplinary
Jacqueline R. Santhouse, Jeremy M. G. Leung, Lillian T. Chong, W. Seth Horne
Summary: By studying the folding kinetics and mechanism of the BdpA sequence, researchers found that altering the backbone connectivity can affect protein folding. This suggests that protein mimetic chains have a significant degree of plasticity in transitioning between unfolded and folded states.
Article
Chemistry, Multidisciplinary
Divanshu Gupta, Ralf Einholz, Holger F. Bettinger
Summary: This study presents the first direct spectroscopic evidence of a cyclic seven-membered iminoborane. Compared to linear amino-iminoboranes, this cyclic iminoborane exhibits weakened bond strength and lower Lewis acidity value. The study suggests that the reduced ring strain of cyclic iminoborane prevents nitrogen fixation but allows facile (2 + 2) cycloaddition reaction with C2H4.
Article
Chemistry, Multidisciplinary
Renny Mathew, Aniruddha Mazumder, Praveen Kumar, Julie Matula, Sharmarke Mohamed, Petr Brazda, Mahesh Hariharan, Brijith Thomas
Summary: This study reveals the packing arrangement of partially disordered nitro-perylenediimide (NO2-PDI) using a synergistic approach that combines 3D ED, ssNMR, and DFT techniques. By overcoming these challenges, this methodology opens up new avenues for material characterization, driving exciting advancements in the field.