Beilstein Journal of Organic Chemistry This is an RSS file. You can use it to subscribe to this data in your favourite RSS reader or to display this data on your own website or blog.

An alternative C – P cross-coupling route for the synthesis of novel V-shaped aryldiphosphonic acids
We report an alternative method that requires no solvent and involves a different order of addition of reactants to perform the transition-metal-catalyzed C–P cross-coupling reaction, often referred to as the Tavs reaction, employing NiCl2 as a pre-catalyst in the phosphonylation of aryl bromide substrates using triisopropyl phosphite. This new method was employed in the synthesis of three novel aryl diphosphonate esters which were subsequently transformed to phosphonic acids through silylation and hydrolysis. Beilstein J. Org. Chem. 2022, 18, 1518–1523. doi:10.3762/bjoc.18.160 (Source: Beilstein Journal ...
Source: Beilstein Journal of Organic Chemistry - November 7, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: arylphosphonic acids cross-coupling reaction phosphonate esters transition-metal catalysis Letter Source Type: research

Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities
Abstract The acceptorless dehydrogenative coupling (ADC) reaction is an efficient method for synthesizing quinoline and its derivatives. In this paper, various substituted quinolines were synthesized from 2-aminobenzyl alcohols and aryl/heteroaryl/alkyl secondary alcohols in one pot via a cyclometalated iridium-catalyzed ADC reaction. This method has some advantages, such as easy availability of raw materials, mild reaction conditions, wide range of substrates, and environmental friendliness which conforms to the principles of green chemistry. Furthermore, a gram-scale experiment with low catalyst loading offers the potent...
Source: Beilstein Journal of Organic Chemistry - October 27, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: acceptorless dehydrogenative coupling reaction antibacterial cyclometalated iridium complexes quinolines Full Research Paper Source Type: research

Molecular and macromolecular electrochemistry: synthesis, mechanism, and redox properties
Beilstein J. Org. Chem. 2022, 18, 1505–1506. doi:10.3762/bjoc.18.158 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - October 26, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: electron transfer electrosynthesis organic electrochemistry redox-active materials Editorial Source Type: research

Comparison of crystal structure and DFT calculations of triferrocenyl trithiophosphite ’ s conformance
Abstract A triferrocenyl trithiophosphite was studied by X-ray single-crystal diffraction. Triferrocenyl trithiophosphite has nine axes of internal rotation: three P–S bonds, three C–S bonds and three Fe–cyclopentadienyl axes. Rotation around the P–S bonds results in a totally asymmetric structure with three ferrocenylthio groups exhibiting different orientations towards the phosphorus lone electron pair (LEP). A comparison of DFT calculations and X-ray diffraction data is presented, herein we show which conformations are preferred for a given ligand. Beilstein J. Org. Chem. 2022, 18, 1499–15...
Source: Beilstein Journal of Organic Chemistry - October 25, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: DFT calculations multi-ferrocenyl compounds phosphorus thioesters trithiophosphite X-ray Full Research Paper Source Type: research

Microelectrode arrays, electrosynthesis, and the optimization of signaling on an inert, stable surface
Abstract Microelectrode arrays are powerful tools for monitoring binding interactions between small molecules and biological targets. In most cases, molecules to be studied using such devices are attached directly to the electrodes in the array. Strategies are in place for calibrating signaling studies utilizing the modified electrodes so that they can be quantified relative to a positive control. In this way, the relative binding constants for multiple ligands for a receptor can potentially be determined in the same experiment. However, there are applications of microelectrode arrays that require stable, tunable, and chem...
Source: Beilstein Journal of Organic Chemistry - October 20, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: calibration of binding curves electrochemical signaling microelectrode array Full Research Paper Source Type: research

One-pot synthesis of 2-arylated and 2-alkylated benzoxazoles and benzimidazoles based on triphenylbismuth dichloride-promoted desulfurization of thioamides
This study presents the first use of triphenylbismuth dichloride to produce benzimidoyl chloride from thioamides by desulfurization and chlorination, as well as its application to the synthesis of 2-substituted benzazoles. Beilstein J. Org. Chem. 2022, 18, 1479–1487. doi:10.3762/bjoc.18.155 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - October 18, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: benzazole bismuth cyclization desulfurization thioamide Full Research Paper Source Type: research

Design, synthesis, and evaluation of chiral thiophosphorus acids as organocatalysts
Abstract A series of P-stereogenic chiral phosphorus acids (CPAs) were synthesized to determine the requirements for efficient asymmetric organocatalysis. In order to eliminate the need for C2-symmetry in common CPAs, various scaffolds containing C1-symmetrical thiophosphorus acids were chosen. These new compounds were synthesized and evaluated in the asymmetric transfer hydrogenation of 2-phenylquinoline. Although the efficacy of the thiophosphorus acids was disappointing for this reaction, the work should be useful for developing structural design elements. Beilstein J. Org. Chem. 2022, 18, 1471–1478. doi:10....
Source: Beilstein Journal of Organic Chemistry - October 17, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: asymmetric heterocycles organocatalysis phosphorus synthesis Full Research Paper Source Type: research

Supramolecular approaches to mediate chemical reactivity
Beilstein J. Org. Chem. 2022, 18, 1463–1465. doi:10.3762/bjoc.18.152 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - October 14, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: Editorial Source Type: research

Synthesis of the biologically important dideuterium-labelled adenosine triphosphate analogue ApppI(d2)
Abstract The chemical synthesis of the dideuterium-labelled ATP analogue 1-adenosin-5’-yl-3-(3-methylbut-3-en-1,1-d2-1-ol) triphosphoric acid diester (ApppI(d2)) is described. ApppI has been reported to be an important mevalonate pathway metabolite, induced by nitrogen-containing bisphosphonates used for the treatment of several diseases related to the calcium metabolism, of which osteoporosis is the most well-known. The availability of ApppI(d2) opens possibilities to quantitative measurements of ApppI in biological samples by mass spectrometry. The synthesized target compound ApppI(d2) was purified by high-performa...
Source: Beilstein Journal of Organic Chemistry - October 14, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: ApppI ATP deuterium labelling HPCCC mevalonate pathway NMR synthesis Letter Source Type: research

Oxa-Michael-initiated cascade reactions of levoglucosenone
Abstract The reactions of aromatic aldehydes and levoglucosenone promoted by methoxide gives bridged α,β-unsaturated ketones, formed by a series of oxa-Michael-initiated cascade reactions in yields of up to 91% (14 examples). A complex series of equilibria operate during the reaction, and the formation of the bridged species is thermodynamically favored, except in the case of 5-methylfurfural and pyrrole-2-carboxaldehyde. This is the first report detailing this type of aldol/Michael cascade involving oxa-Michael initiation. Beilstein J. Org. Chem. 2022, 18, 1457–1462. doi:10.3762/bjoc.18.151 (Source: ...
Source: Beilstein Journal of Organic Chemistry - October 13, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: cascade reactions green chemistry levoglucosenone oxa-Michael reaction Full Research Paper Source Type: research

Dissecting Mechanochemistry III
Beilstein J. Org. Chem. 2022, 18, 1454–1456. doi:10.3762/bjoc.18.150 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - October 12, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: Editorial Source Type: research

1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host – guest complexes
Abstract A synthetic route to 1,4,6,10-tetraazaadamantanes (TAADs) bearing free and protected amino groups at the bridge N-atoms has been developed via intramolecular cyclotrimerization of C=N units in the corresponding tris(hydrazonoalkyl)amines. In a similar fashion, unsymmetrically substituted TAADs having both amino and hydroxy groups at the bridge N-atoms were prepared via a hitherto unknown co-trimerization of oxime and hydrazone groups. The use of N-TAAD derivatives as potential ligands and receptors was showcased through forming boron chelates and host–guest complexes with water and simple alcohols. Beilstei...
Source: Beilstein Journal of Organic Chemistry - October 11, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: azaadamantanes cyclotrimerization hydrazones inclusion complexes molecular recognition Full Research Paper Source Type: research

Naphthalimide-phenothiazine dyads: effect of conformational flexibility and matching of the energy of the charge-transfer state and the localized triplet excited state on the thermally activated delayed fluorescence
Abstract In order to investigate the joint influence of the conformation flexibility and the matching of the energies of the charge-transfer (CT) and the localized triplet excited (3LE) states on the thermally activated delayed fluorescence (TADF) in electron donor–acceptor molecules, a series of compact electron donor–acceptor dyads and a triad were prepared, with naphthalimide (NI) as electron acceptor and phenothiazine (PTZ) as electron donor. The NI and PTZ moieties are either directly connected at the 3-position of NI and the N-position of the PTZ moiety via a C–N single bond, or they are linked thro...
Source: Beilstein Journal of Organic Chemistry - October 11, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: charge-transfer electron donor intersystem crossing TADF triplet state Full Research Paper Source Type: research

Mechanochemical synthesis of unsymmetrical salens for the preparation of Co – salen complexes and their evaluation as catalysts for the synthesis of α -aryloxy alcohols via asymmetric phenolic kinetic resolution of terminal epoxides
Abstract In this paper, we report the mechanochemical synthesis of unsymmetrical salens using grinding and ball milling technologies, respectively, both of which were afforded in good yield. The chelating effect of the unsymmetrical salens with zinc, copper, and cobalt was studied and the chiral Co–salen complex 2f was obtained in 98% yield. Hydrolytic kinetic resolution (HKR) of epichlorohydrin with water catalyzed by complex 2f (0.5 mol %) was explored and resulted in 98% ee, suggesting complex 2f could serve as an enantioselective catalyst for the asymmetric ring opening of terminal epoxides by phenols. A library ...
Source: Beilstein Journal of Organic Chemistry - October 10, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: α -aryloxy alcohols chiral Co – salen HKR mechanochemistry phenolic KR Letter Source Type: research

Sinensiols H – J, three new lignan derivatives from Selaginella sinensis (Desv.) Spring
Abstract One new lignan sinensiol H (1) and two new bisnorlignans, sinensiols I and J (2 and 3), along with three known compounds were isolated from the whole plants of Selaginella sinensis. Their structures were elucidated on the basis of 1D and 2D NMR spectroscopy as well as high-resolution mass spectrometry. The absolute configuration of 1 was established by ECD calculation. Compounds 2 and 3 represent rare examples of naturally occurring 9,9'-bisnorlignans. All the isolated compounds were assayed for their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages. Beilstein J. Org. Chem. 2...
Source: Beilstein Journal of Organic Chemistry - October 7, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: lignan derivatives nitric oxide production inhibition norlignans Selaginella sinensis Full Research Paper Source Type: research