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Multi-substituted trifluoromethyl alkene construction via gold-catalyzed fluoroarylation of gem-difluoroallenes† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d3sc06060h

ABSTRACT:

SUBMITTER: Li Z

PROVIDER: S-EPMC10915851 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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The power of microdroplet photochemistry† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d4sc00056k

Project description: Not available

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Total synthesis of bi-magnolignan† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d3ra01121f

Project description:Bi-magnolignan, isolated from the leaves of Magnolia officinalis, has shown excellent physiological activity against tumor cells. An efficient strategy for the first total synthesis of bi-magnolignan is reported. The bi-dibenzofuran skeleton was constructed via functional group interconversions of commercially available materials 1,2,4-trimethoxybenzene and 4-allylanisole. Then, the dibenzofuran skeleton was afforded by subsequent Suzuki coupling and intramolecular dehydration. The total synthesis of natural product was accomplished through FeCl3 catalyzed oxidative coupling. The first total synthesis of bi-magnolignan in eight steps from commercially available starting materials has been developed.

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Boric acid catalysed hydrolysis of peroxyacids† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d3ra01046e

Project description:This study shows for the first time that boric acid catalyses the hydrolysis of peroxyacids, resulting in an approximately 12-fold increase in hydrolysis rate for both peracetic acid (PAA) and 3-chloroperbenzoic acid (MCPBA) when 0.1 M boric acid is present. The maximum rate of hydrolysis occurs at pH 9 and pH 8.4 for PAA and MCPBA respectively. In contrast, carbonate buffer does not enhance the rate of PAA hydrolysis. The reaction was followed by measuring the initial rate of hydrogen peroxide formation using a specific Ti(iv) complexation method. The study of the hydrolysis reaction requires the presence of 2 × 10−5 M each of ethylenediaminetetraacetic acid (EDTA) and ethylenediamine tetramethylene phosphonic acid (EDTMP) in all solutions in order to chelate metal ions across the full pH range (3 to 13) that would otherwise contribute to peroxyacid decomposition. Catalysis of peroxyacid hydrolysis is most likely effected by the triganol boric acid acting as a Lewis acid catalyst, associating with the peroxide leaving group in the transition state to reduce the leaving group basicity. The products of the reaction are the well characterised monoperoxoborate species and the parent carboxylic acid. Analysis of the pH and borate dependence data reveals that in addition to a catalytic pathway involving a single boric acid molecule, there is a significant pathway involving either (a) two boric acid molecules or (b) the polyborate species, B3O3(OH)4−. Knowledge about catalytic mechanisms for the loss of peroxyacids through hydrolysis is important because they are widely used in reagents in a range of oxidation, bleaching and disinfection applications. Boric acid catalyses the hydrolysis of peroxyacids, with possible pathways involving one and two molecules of boric acid as well as polyborate species.

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AI facilitated fluoro-electrochemical phytoplankton classification† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d3sc01741a

Project description:Marine phytoplankton is extremely diverse. Counting and characterising phytoplankton is essential for understanding climate change and ocean health not least since phytoplankton extensively biomineralize carbon dioxide whilst generating 50% of the planet's oxygen. We report the use of fluoro-electrochemical microscopy to distinguish different taxonomies of phytoplankton by the quenching of their chlorophyll-a fluorescence using chemical species oxidatively electrogenerated in situ in seawater. The rate of chlorophyll-a quenching of each cell is characteristic of the species-specific structural composition and cellular content. But with increasing diversity and extent of phytoplankton species under study, human interpretation and distinction of the resulting fluorescence transients becomes increasingly and prohibitively difficult. Thus, we further report a neural network to analyse these fluorescence transients, with an accuracy >95% classifying 29 phytoplankton strains to their taxonomic orders. This method transcends the state-of-the-art. The success of the fluoro-electrochemical microscopy combined with AI provides a novel, flexible and highly granular solution to phytoplankton classification and is adaptable for autonomous ocean monitoring. Schematic of fluoro-electrochemical microscopy. (a) Cartoon E. huxleyi is green under normal light, but (b) emits red fluorescence under UV. (c) Placed near an oxidizing electrode, its fluorescence fades and ultimately (d) “switches off”.

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Electrically conductive [Fe4S4]-based organometallic polymers† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d3sc02195e

Project description: Not available

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Concise two-step chemical synthesis of molnupiravir† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d2ra05064a

Project description:A concise synthesis of molnupiravir in a one-pot two-step approach starting from uridine is described. Formally, herein, two sets of one-pot two-reaction steps introducing simplicity for purifications and using chemically available reagents are presented. In this context, molnupiravir was obtained in up to 68% overall yield and multigram-scale. In addition, HPLC analysis showed the molnupiravir purity above 99%. Fast, effective and chromatography column-free chemical synthesis of molnupiravir.

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Deaminative coupling of benzylamines and arylboronic acids† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d2sc06055h

Project description:A metal-free deaminative coupling of non-prefunctionalised benzylamines and arylboronic acids is reported. In this operationally simple reaction, a primary amine in benzylamine is converted into a good leaving group in situ using inexpensive and commercially available isoamyl nitrite as a nitrosating reagent. Lewis-acidic arylboronic acids are shown to replace mineral acids such as HCl or HBF4 that are conventionally used in the preparation of aryl diazonium salts. This unlocked the formation of the corresponding diarylmethanes by forging a new C–C bond in good yields. A metal-free deaminative coupling of non-prefunctionalised benzylamines and arylboronic acids is reported.

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Pathway-dependent supramolecular polymerization by planarity breaking† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d4sc02499k

Project description: Not available

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Rh-catalyzed alkoxycarbonylation of unactivated alkyl chlorides† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d2sc04103k

Project description:A general rhodium-catalyzed selective carbonylative coupling of unactivated alkyl chlorides with aliphatic alcohols or phenols to the corresponding esters is presented for the first time. Crucial for this transformation is the addition of sodium iodide, which provides in situ more active alkyl iodides. In the presence of a Rh(i)-DPPP catalyst system diverse esters (81 examples) including industrially relevant acetates from chloro- and dichloromethane can be prepared in a straightforward manner in up to 95% isolated yield. The used ligand not only affects the selectivity of the carbonylation reaction but also controls the selectivity of the preceding halide exchange step. An efficient and convenient rhodium-catalyzed alkoxycarbonylation of unactivated alkyl chlorides was developed for the first time. More than 80 examples of esters were prepared directly from readily available substrates with often high selectivity.

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Hidden hydrophobicity impacts polymer immunogenicity† † Electronic supplementary information (ESI) available: Experimental details and supplementary figures. See DOI: https://doi.org/10.1039/d2sc07047b

Project description:Antibodies against poly(ethylene glycol) (PEG) have been found to be the culprit of side reactions and efficacy loss of a number of PEGylated drugs. Fundamental mechanisms of PEG immunogenicity and design principles for PEG alternatives still have not been fully explored. By using hydrophobic interaction chromatography (HIC) under varied salt conditions, we reveal the “hidden” hydrophobicity of those polymers which are generally considered as hydrophilic. A correlation between the hidden hydrophobicity of a polymer and its polymer immunogenicity is observed when this polymer is conjugated with an immunogenic protein. Such a correlation of hidden hydrophobicity vs. immunogenicity for a polymer also applies to corresponding polymer–protein conjugates. Atomistic molecular dynamics (MD) simulation results show a similar trend. Based on polyzwitterion modification and with this HIC technique, we are able to produce extremely low-immunogenic protein conjugates as their hydrophilicity is pushed to the limit and their hydrophobicity is eliminated, breaking the current barriers of eliminating anti-drug and anti-polymer antibodies. The hidden hydrophobicity of conventional polymers widely considered as hydrophilic is closely related to their immunogenicity when they are conjugated to immunogenic proteins.

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