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Kinetic resolution of 1,1'-binaphthyl-2,2'-diamine derivatives by chiral calcium phosphate-catalyzed acylation

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00355A, Paper
Tatsuhiro Uchikura, Yuki Kanno, Yukino Fukuda, Mikoto Sato, Takahiko Akiyama
Chiral calcium phosphate-catalyzed kinetic resolution of BINAM derivatives.
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On the mechanism of carboxylate elimination from carbohydrate monoester-derived radicals

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00241E, Communication
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Julia A. Turner, Hendrik Zipse, Mark S. Taylor
Computational analysis of the HAT-induced expulsion of carboxylic acids from monoacylated pyranosides implicates concerted elimination through a hydrogen-bonded transition state.
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An efficient synthesis of mono-, di-, and tri-substituted 1,3-thiazoles employing functionalized thioamides as thiocarbonyl precursors

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00229F, Paper
Kalleshappa Sheela, Chikkappaiahnayaka Santhosh, Krishna Ravi Singh, Kalleshappa Sharath, Maralinganadoddi P. Sadashiva
Herein, we report an efficient strategy to synthesize functionalized 1,3-thiazoles using alkyl 2-amino-2-thioxoacetates.
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Photoinduced decatungstate-catalyzed C(sp3)–H thioetherification by sulfinate salts

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00394B, Paper
Pengcheng Li, Jia-Lin Tu, Ao-Men Hu, Lin Guo, Chao Yang, Wujiong Xia
A visible light photoinduced decatungstate-catalyzed C(sp3)–H thioetherification of hydrocarbons by sodium sulfite is herein reported.
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A copper-catalyzed asymmetric Friedel–Crafts hydroxyalkylation of pyrazole-4,5-diones with 5-aminoisoxazoles

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00322E, Communication
Siyu Gao, Xiang Sun, Sijie Peng, Zhenggen Zha, Qi Sun, Zhiyong Wang
An asymmetric Friede-Crafts hydroxyalkylation reaction was developed under the catalysis of chiral copper complexes. A variety of pyrazolone derivatives were obtained with excellent yields and enantioselectivities.
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Synthesis of fluorescent 5-heteroarylpyrimidine-containing oligonucleotides via post-synthetic trifluoromethyl conversion

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00402G, Paper
Yuta Ito, Hisato Tanaka, Ayana Murakami, Yasufumi Fuchi, Yoshiyuki Hari
5-(Benzimidazol-2-yl)- and 5-(benzothiazol-2-yl)-pyrimidine bases-modified oligonucleotides were prepared by post-synthetic trifluoromethyl conversion and their fluorescence properties were measured.
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Friedel–Crafts reactions for biomolecular chemistry

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00406J, Review Article
Open Access
Jun Ohata
This review demonstrates advances in Friedel–Crafts alkylation and acylation reactions in a variety of biomolecular chemistry fields.
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Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00393D, Paper
Rasmita Barik, Samik Nanda
Naturally occurring sesquiterpenes having humulane frameworks are structurally intriguing and possess significant biological profiles.
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Structural flexibility of favipiravir and its structural analogues in solutions: experimental and computational insight

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00404C, Paper
Tatiana P. Gerasimova, Almaz A. Zagidullin, Anastasiia N. Nikolaeva, Robert R. Fayzullin, Aliya M. Saitova, Vasili A. Miluykov, Stefan Grimme, Sergey A. Katsyuba
Keto-enol transformations of 6-R-3-hydroxy-2-pyrazinecarboxamides in solutions are accompanied by deprotonation of enol tautomers and the formation of corresponding anionic species. The key factors determining these processes have been identified.
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Catalyst- and base-free visible light-enabled radical relay trihalomethylation/functional group-migration/carbonylation with CX3SO2Cl

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00292J, Paper
Jinkai Hu, Chenglei Yang, Xiaotao Qin, Hui Liu, Tongtong Ma, Ao-tong Shi, Qing-Long Lv, Xingman Liu, Jinhui Yang, Dianjun Li
A visible light-enabled photocatalyst-free radical trihalomethylation/cyano (or benzo[d]thiazol-2-yl) 1,4-migration/carbonylation reaction of 2-hydroxy-2-hex-5-enenitrile (or (benzo[d]thiazol-2-yl)-pent-4-enol) with CX3SO2Cl (X = F, Cl) is reported.
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Stereoselective Synthesis of gem-Dihalopiperidines via Halo-Aza-Prins Cyclization Reaction: Access to Piperidin-4-ones and Pyridines

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00338A, Paper
Anil Kumar Saikia, Surjya Kumar Bora, Subhamoy Biswas, Bipin Kumar Behera
An efficient methodology for the synthesis of 4,4-dihalopiperidine derivatives has been developed from N-(3-halobut-3-en-1-yl)-4-methylbenzenesulfonamide and aldehyde catalyzed by In(OTf)3 in excellent yields. The reaction involves an initial formation of six...
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Covalently linked thieno[2,3-b]thiophene-fullerene dimers: synthesis and physical characterization

Org. Biomol. Chem., 2024, 22,2978-2984
DOI: 10.1039/D4OB00027G, Paper
Abdulrahman M. Alazemi, Mohammad H. BinSabt, Hamad M. Al-Matar, Alan L. Balch, Mona A. Shalaby
Linked thieno[2,3-b]thiophene-fullerene Dimers.
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Asymmetric synthesis of the fully functionalized six-membered A-ring of siphonol A

Org. Biomol. Chem., 2024, 22,2958-2962
DOI: 10.1039/D4OB00104D, Communication
Ying Sun, Shaomin Fu, Bo Liu
The asymmetric synthesis of the fully functionalized six-membered A-ring of siphonol A is presented.
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Hydrosilylation of nitriles and tertiary amides using a zinc precursor

Org. Biomol. Chem., 2024, 22,3053-3058
DOI: 10.1039/D4OB00161C, Paper
Ravi Kumar, Rohan Kumar Meher, Himadri Karmakar, Tarun K. Panda
A competent and selective hydrosilylation of nitriles and tertiary amides catalyzed by zinc bis(hexamethyldisilazide) [Zn(HMDS)2] under solvent-free and mild conditions are reported, as a sustainable and desirable alternative to existing methods.
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Expanding the scope of the successive ring expansion strategy for macrocycle and medium-sized ring synthesis: unreactive and reactive lactams

Org. Biomol. Chem., 2024, 22,2985-2991
DOI: 10.1039/D4OB00285G, Paper
Open Access
Zhongzhen Yang, Marion Arnoux, Damien Hazelard, Owen R. Hughes, Joe Nabarro, Adrian C. Whitwood, Martin A. Fascione, Christopher D. Spicer, Philippe Compain, William P. Unsworth
New Successive Ring Expansion (SuRE) protocols are described for use on unreactive lactams, as well as iminosugar derived lactams.
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Photogenerated chlorine radicals activate C(sp3)–H bonds of alkylbenzenes to access quinazolinones

Org. Biomol. Chem., 2024, 22,2968-2973
DOI: 10.1039/D4OB00129J, Communication
Xin-Yao Pan, Gui-Xia Sun, Fang-Ping Huang, Wen-Jian Qin, Qing-Hu Teng, Kai Wang
An Fe-catalyzed visible-light induced condensation of alkylbenzenes with anthranilamides has been developed.
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Unusual immunosuppressive pyridine-containing bisnor- (c23), tetranor- (c21) and pentanor- (c20) sesterterpenoids from Tibetan Leucosceptrum canum

Org. Biomol. Chem., 2024, 22,3019-3024
DOI: 10.1039/D4OB00334A, Paper
Man Li, Ling Feng, Han Zhang, Yan-Chun Liu, Ting-Ting Zhou, Yu Zheng, Kai Guo, Yan Liu, Sheng-Hong Li
Six unusual pyridine-containing bisnor- (C23), tetranor- (C21) and pentanor- (C20) sesterterpenoids were obtained from the medicinal plant Leucosceptrum canum of Tibetan origin. The immunosuppressive activities of these sesterterpenoids were observed.
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Synthesis of alkynyl sulfides via base-promoted nucleophilic ring-opening of α-bromostyrene sulfonium salt

Org. Biomol. Chem., 2024, 22,2953-2957
DOI: 10.1039/D4OB00203B, Communication
Junqi Zhou, Ziyu Wang, Hanmiao Xu, Mengke Su, Jian Wen
An effective method for synthesizing various alkynyl sulfides has been developed using tetramethylene sulfoxide as a sulfur source through base-promoted nucleophilic ring-opening reactions.
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Identification and quantification of local antiaromaticity in polycyclic aromatic hydrocarbons (PAHs) based on the magnetic criterion

Org. Biomol. Chem., 2024, 22,3035-3044
DOI: 10.1039/D4OB00114A, Paper
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Erich Kleinpeter, Andreas Koch
The ring current effect of entirely and partly (anti)aromatic PCHs are calculated and employed to visualize, qualify and quantify existing (anti)aromaticity, especially to decide unequivocally between PAHs and PAAHs.
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A pyridine-N-oxide catenane for cation recognition

Org. Biomol. Chem., 2024, 22,3001-3008
DOI: 10.1039/D4OB00176A, Paper
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Sean R. Barlow, Nathan R. Halcovitch, Nicholas H. Evans
A pyridine-N-oxide containing [2]catenane may be reversibly protonated, as well as bind lithium cations more strongly than sodium cations.
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Stereoselective synthesis of (R)- and (S)-1,2-diazetidine-3-carboxylic acid derivatives for peptidomimetics

Org. Biomol. Chem., 2024, 22,2974-2977
DOI: 10.1039/D4OB00278D, Communication
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Matthew Nutter, Henry Stone, Michael Shipman, Stefan Roesner
Stereoselective synthesis of both enantiomers of orthogonally protected 1,2-diazetidine-3-carboxylic acid (aAze) from homochiral glycidol and its application in peptidomimetics.
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Additive-free oxychlorination of unsaturated C–C bonds with tert-butyl hypochlorite and water

Org. Biomol. Chem., 2024, 22,3080-3085
DOI: 10.1039/D4OB00003J, Paper
Duyi Shen, Chaoyue Sun, Yun Han, Zhen Luo, Ting Ren, Qin Zhang, Wenting Huang, Jianru Xie, Ying Jia, Mianran Chao
A facile oxychlorination of various alkynes and alkenes with tBuOCl as an alternative chlorine source and H2O as a green oxygen source.
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Selective enhancement of (6–4) photoproduct formation in dithymine dinucleotides driven by specific sugar puckering

Org. Biomol. Chem., 2024, 22,3025-3034
DOI: 10.1039/D4OB00279B, Paper
Jouda Jakhlal, Clément Denhez, Stéphanie Coantic-Castex, Agathe Martinez, Dominique Harakat, Thierry Douki, Dominique Guillaume, Pascale Clivio
Evidence is presented that (6–4) photoproduct formation between two thymine residues in dinucleotide analogues is significantly and specifically enhanced when the 5''- and 3''-end sugar puckering are mainly north and south, respectively.
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Iron-catalyzed selective construction of indole derivatives via oxidative C(sp3)–H functionalization of indolin-2-ones

Org. Biomol. Chem., 2024, 22,3073-3079
DOI: 10.1039/D4OB00133H, Paper
Wei Chen, Lang-Qi Wen, Xiao-Bing Lu, Hui Zhou
We have developed a clean and efficient iron-catalyzed C(sp3)–H functionalization of indolin-2-ones for the chemodivergent synthesis of value-added indole derivatives, including isatins, and symmetrical and non-symmetrical isoindigos.
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Direct access to pyrrole anhydrides via oxidative self-coupling of pyrrole carboxaldehydes

Org. Biomol. Chem., 2024, 22,3045-3052
DOI: 10.1039/D4OB00052H, Paper
Surabhi Panday, Tapas Maity, Pratibha Bhatti, Joydev K. Laha
An elegant synthesis of pyrrole-2-carboxylic acid anhydrides from pyrrole-2-carboxaldehydes using TBAI as a catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant is described herein.
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Photochromism of phenazine-2,3-diol derivatives through excited state intermolecular proton transfer based on keto–enol tautomerization

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00387J, Paper
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Kazuki Ohira, Kumpei Kozuka, Naoki Kaneda, Masahiro Yamamoto, Keiichi Imato, Yousuke Ooyama
It was found that phenazine-2,3-diol derivatives exhibit photochromism through excited state intermolecular proton transfer (ESInterPT) processes based on keto–enol tautomerization.
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Charge-transfer inclusion complex formation of the tropylium cation with prism[6]arenes

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00423J, Communication
Guojiao Zhang, Channi Cheng, Zhengxiang Li, Dezhi Zhao, Chengyou Han
We report that charge-transfer (CT) inclusion complexes were formed between prism[6]arenes and tropylium cation. Additionally, the CT complex showed Cl/Ag+ responsiveness which can be easily monitored by the naked eye.
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Exploring the mechanism of the reductive amination of acetophenones via Borch approach: the role of the acid catalyst

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00160E, Paper
João Pedro Albuquerque Souza, Amanda Krauskopf Jacobs, Leandro Piovan, Renan Borsoi Campos
The energetic viability of several mechanistic variations of the reductive amination of acetophenones via the Borch approach was reexamined through density functional theory calculations. The crucial involvement of the acid...
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3-Halo-5,6-dihydro-4H-1,2-oxazine N-oxides as synthetic equivalents of unsaturated nitrile oxides in the [3 + 2]-cycloaddition with arynes: synthesis of substituted 3-vinyl-1,2-benzisoxazoles

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00391H, Communication
Alexander A. Lukoyanov, Svetlana A. Aksenova, Andrey A. Tabolin, Alexey Yu. Sukhorukov
3-Halo-1,2-oxazine N-oxide derivatives act as surrogates of vinyl nitrile oxides in tandem [3 + 2]-cycloaddition/[3 + 2]-cyclofragmentation with arynes leading to benzisoxazoles.
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Cu(OTf)2/HFIP catalyzed regioselective cycloisomerization of indole-C3-functionalized alkynols to carbazoles

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00421C, Communication
Srinivasarao Yaragorla, Tabassum Khan, Sayonika Chakroborty
We report here a simple and atom economic cycloisomerization reaction of indole-tethered alkynols for constructing diverse carbazoles via 1,2-alkly migration using Cu(OTf)2/HFIP as the excellent promoter system.
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Dess–Martin periodinane-mediated oxidation of the primary alcohol of cytidine into a carboxylic acid

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00240G, Communication
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Alexandra R. E. Serre, Vibhu Jha, Adèle Rivault, Leif A. Eriksson, Goreti Ribeiro Morais, Robert A. Falconer
Herein we describe the first example of the conversion of the primary alcohol of cytidine into a carboxylic acid by use of the Dess–Martin periodinane oxidising agent.
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Photoproperties of Favipiravir and their 6-Substituted Analogues: Fluorescence Controlled through Halogen Substitution and Tautomerism

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00397G, Paper
Angel H Romero, Marcos Couto, Ivan E Romero, German Fuentes, Matías N. Möller
Herein, we showed the photophysical properties of the favipiravir and their 6-substituted analogues. Also, we interpreted the origin of the fluorescence of the favipiravir and their 6-substituted analogues as function...
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Design, synthesis, biological evaluation and molecular docking studies of quinoline-anthranilic acid hybrids as potent anti-inflammatory drugs

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00040D, Paper
Sidra Siddique, Khalid Hussain, Naureen Shehzadi, Muhammad Arshad, Muhammad Nadeem Arshad, Sadaf Iftikhar, Farhat Saghir, Ayisha Shaukat, Muhammad Sarfraz, Nisar Ahmed
Despite the high global prevalence, rheumatoid arthritis lacks a satisfactory treatment.
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Discovery of selective monosaccharide receptors via dynamic combinatorial chemistry

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00015C, Communication
Open Access
  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Miguel Alena-Rodriguez, Marcos Fernandez-Villamarin, Ignacio Alfonso, Paula M. Mendes
An effective workflow to discover selective saccharide receptors by combining dynamic combinatorial chemistry with isothermal titration calorimetry and NMR.
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Synthesis of Deuteriodifluoromethylthiolated Isocoumarins-1- imines and Isocoumarins Enabled by Multi-Component Reagents System (MCRS)

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00328D, Communication
Xuemin Li, Haofeng Shi, Jiaxin He, Jialiang Wu, Fengxia Sun, Yunfei Du
The combining use of BnSCF2D, mCPBA and Tf2O serves as an efficient multi-component reagents system (MCRS) for the synthesis of deuteriodifluoromethylthiolated isocoumarins-1-imines/isocoumarins via intramolecular cyclization/ deuteriodifluoromethylthiolation of 2-alkynylbenzamide/2-alkynylbenzoates. The approach...
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An FeCl3-catalyzed three-component reaction for the synthesis of β-(1,2,3-triazolyl)-ketones using DMF as a one-carbon source

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00207E, Communication
Ruilin Fang, Lei Zheng, Xuyang Chen, Can Wang, Yunfeng Chen
FeCl3-catalyzed oxidative condensation of NH-1,2,3-triazoles and aryl methyl ketones and DMF has been reported.
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Measuring local pH at interfaces from molecular tumbling: A concept for designing EPR-active pH-sensitive labels and probes

Org. Biomol. Chem., 2024, Advance Article
DOI: 10.1039/D4OB00167B, Paper
Open Access
Maxim A. Voinov, Nicholas Nunn, Roshan Rana, Atli Davidsson, Alex I. Smirnov, Tatyana I. Smirnova
EPR-based local pH measurements based on changes in rotational dynamics of spin-bearing molecules upon protonation.
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Facile synthesis of tetrahydroquinoline containing dithiocarbamate derivatives via one-pot sequential multicomponent reaction

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00490F, Communication
SIDDHARTHA KUMAR SENAPATI, Anit Pal, Animesh Das
An efficient sequential multi-component method for the synthesis of tertrahydroquinoline containing dithiocarbamate has been developed. This reaction involved a boronic acid-catalyzed reduction of quinoline to tertrahydroquinoline, followed by nucleophilic addition...
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N-Functionalization of beta-aminophosphonates; Cytotoxic effect of the new derivatives

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00243A, Paper
György Keglevich, Petra Regina Varga, Emőke Dinnyési, Zsuzsanna Szalai, Szilvia Bősze, Rita Oláhné Szabó, Laszlo Drahos, Konstantin Karaghiosoff
Beta-Aminophosponates obtained by the Michael addition of primary amines to the double bond of diethyl vinylphosphonate proved to be suitable starting materials (amine components) in the Kabachnik–Fields reaction with formaldehyde...
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Visible light-driven photocatalytic sulfonative oxidation of benzyl secondary amines

Org. Biomol. Chem., 2024, Accepted Manuscript
DOI: 10.1039/D4OB00348A, Paper
Yong-Xiang Lü, Xinqian Wang, Ying-Ming Pan, Keyume Ablajan
A method for the α-oxidation and sulfonation of benzyl secondary amines was developed utilizing Ir(III) or Eosin Y as the photocatalyst in the presence of O2 as a green oxidant....
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The Hobbit Experience 2014: Adding WebRTC gameplay to the Hobbit Experience

Learn how North Kingdom built an immersive multimedia experience optimized for modern mobile browsers using Web RTC




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Tab Discarding in Chrome: a Memory-Saving Experiment




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As the price of aviation turbine fuel soars, airlines’ finances spin out of control




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Walking through a new airport experience

Automation and biometrics will be the norm rather than the exception at leading airports in the pandemic world




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Gearing up to fly twice as fast as sound

The US-based start-up Boom Supersonic is putting together an aircraft that can fly at a maximum speed of Mach 2.2




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Pandemic: Contactless technology on an overdrive

As demand for travel rises, industry must meet it while ensuring passenger safety




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Deep tech is helping airlines sustain operations during Covid

Integrated biometric-enabled frameworks for real-time test results, travel details and vaccine status are key to making air travel safe




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Breaking down airline engineering and maintenance

An aircraft has three critical phases; induction, in-service and redelivery




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Air crew at higher risk




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From geopolitics strife to a war of words between two aviation giants

Qatar Airways and Airbus lock horns over safety concerns