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Search for "deuterium" in Full Text gives 160 result(s) in Beilstein Journal of Organic Chemistry.

Copper-catalyzed yne-allylic substitutions: concept and recent developments

  • Shuang Yang and
  • Xinqiang Fang

Beilstein J. Org. Chem. 2024, 20, 2739–2775, doi:10.3762/bjoc.20.232

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  • , 50a–l) axial chirality in remarkable enantiopurities. Mechanistic studies and deuterium labeling experiments have revealed that the reaction proceeds in a stepwise manner without involving a 1,5-H migration process. Based on these findings, the authors have proposed a mechanism wherein the
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Published 31 Oct 2024

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

  • Nian Li,
  • Ruzal Sitdikov,
  • Ajit Prabhakar Kale,
  • Joost Steverlynck,
  • Bo Li and
  • Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

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Published 09 Oct 2024

Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various nucleophiles

  • Yutaro Miyashita,
  • Sae Someya,
  • Tomoko Kawasaki-Takasuka,
  • Tomohiro Agou and
  • Takashi Yamazaki

Beilstein J. Org. Chem. 2024, 20, 2421–2433, doi:10.3762/bjoc.20.206

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  • the production of the possible olefinic product n-C8H17CH=CH2. Moreover, when the reaction mixture was quenched with D2O, incorporation of deuterium was observed to give 11a-D in a high yield which allowed us to conclude the possible presence of the C-copper species just before quenching. Our result
  • of the reductive elimination very slow, the intermediary Cu(III) species safely existed until the addition of D2O. Because the significant overlap of NMR peaks was observed due to the quite similar structure of 11a and 11a-D, quantitative analysis of the deuterium content of 11a-D was not possible
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Published 25 Sep 2024

Improved deconvolution of natural products’ protein targets using diagnostic ions from chemical proteomics linkers

  • Andreas Wiest and
  • Pavel Kielkowski

Beilstein J. Org. Chem. 2024, 20, 2323–2341, doi:10.3762/bjoc.20.199

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  • that does not necessitate for NP modification might be desirable. This may include hydrogen–deuterium exchange mass spectrometry (HDX-MS), limited proteolysis-coupled mass spectrometry (LiP–MS), thermal proteome profiling (TPP), cellular thermal shift assay (CETSA), affinity selection-mass spectrometry
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Published 12 Sep 2024

Deuterated reagents in multicomponent reactions to afford deuterium-labeled products

  • Kevin Schofield,
  • Shayna Maddern,
  • Yueteng Zhang,
  • Grace E. Mastin,
  • Rachel Knight,
  • Wei Wang,
  • James Galligan and
  • Christopher Hulme

Beilstein J. Org. Chem. 2024, 20, 2270–2279, doi:10.3762/bjoc.20.195

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  • , Tucson, Arizona, 85721, USA 10.3762/bjoc.20.195 Abstract The utility of bio-isosteres is broad in drug discovery and methodology herein enables the preparation of deuterium-labeled products is the most fundamental of known bio-isosteric replacements. As such we report the use of both [D1]-aldehydes and
  • drug-like compounds with synthetic ease [5][6]. In recent years use of deuterium in drug discovery has expanded beyond mechanistic and tracer studies to deuterium incorporation in small molecules in attempts to hijack the deuterium kinetic isotope effect to induce longer drug t1/2 and greater systemic
  • exposure [7][8][9]. Herein, we describe applications of deuterium-labeled reagents with MCRs through use of deuterated aldehydes and deuterated isocyanides, an area of study with sparingly few examples. One example by Srivastava obtained a 65% deuterated Passerini product starting from a 65% deuterated
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Published 06 Sep 2024

Understanding X-ray-induced isomerisation in photoswitchable surfactant assemblies

  • Beatrice E. Jones,
  • Camille Blayo,
  • Jake L. Greenfield,
  • Matthew J. Fuchter,
  • Nathan Cowieson and
  • Rachel C. Evans

Beilstein J. Org. Chem. 2024, 20, 2005–2015, doi:10.3762/bjoc.20.176

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  • viscosity, from 0.89 in H2O to 1.10 mPa⋅s in D2O [42], which is attributed to slow diffusion of micelles within the medium. Furthermore, the rate of H+/D+ exchange between the solvent and the photoswitch will decrease due to the heavier deuterium atoms in D2O, resulting in an effective weakening of the
  • purification system. Hydrobromic acid (48%) and deuterium oxide (99.9 atom %) were supplied by Merck. Sample preparation To produce micellar samples, light-responsive PS were shaken with the solvent (50 mM in either H2O or D2O) until homogenous. For samples of higher concentration, AAPTAB was added to water
  • Journal of Synchrotron Radiation, distributed under the terms of the Creative Commons Attribution 4.0 International License). SAXS curves for the Z-rich PSS of AAPTAB (50 mM) in (a) water (H2O) and (b) deuterium dioxide (D2O) show changes to the micelle shape and size on X-ray exposure. Fits to the data
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Published 14 Aug 2024

A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

  • Ivana Weisheitelová,
  • Radek Cibulka,
  • Marek Sikorski and
  • Tetiana Pavlovska

Beilstein J. Org. Chem. 2024, 20, 1831–1838, doi:10.3762/bjoc.20.161

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  • source in this reaction, a deuterium labelling experiment was conducted (Scheme 2C). Indeed, the deazaalloxazine derivative 6-d with quantitative incorporation of deuterium in C(5) position, was isolated and confirmed by 1H NMR analysis and mass spectrometry (for more details on possible reaction
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Published 31 Jul 2024

Transition-metal-catalyst-free electroreductive alkene hydroarylation with aryl halides under visible-light irradiation

  • Kosuke Yamamoto,
  • Kazuhisa Arita,
  • Masami Kuriyama and
  • Osamu Onomura

Beilstein J. Org. Chem. 2024, 20, 1327–1333, doi:10.3762/bjoc.20.116

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  • hydroarylation product was not observed (Scheme 3b). This result strongly supported the involvement of radical intermediates in the present transformation. Next, a deuterium-labeling experiment was conducted to elucidate the H-source of this reaction (Scheme 3c). The reaction of 1a and 2e in MeCN with D2O
  • provided the coupling product with 51% deuterium incorporation, indicating that carbanion species would be generated in this reaction and that H2O would serve as a major proton source. Et4NCl may also provide protons to form the coupling product [47]. Taken these results together, the present
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Published 10 Jun 2024

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

  • Mohd Farhan Ansari,
  • Atul Kumar Maurya,
  • Abhishek Kumar and
  • Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

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  • condensation with ketones, yielding an α,β-unsaturated compound, which was hydrogenated by the manganese hydride species, resulting in the final alkylated product (Scheme 25). A set of deuterium labelling tests and additional control studies determined that the alcohol dehydrogenation was aided by an
  • substituted primary alcohols gave moderate to good yields (50–82%). Deuterium-labelling experiments with deuterated 1-phenylethanol-α-d1 and benzyl alcohol-α,α-d2 suggested a hydrogen auto-transfer and dehydrogenation process. The amido species Mn18-a generated from Mn18 by the base is responsible for the
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Published 21 May 2024

Advancements in hydrochlorination of alkenes

  • Daniel S. Müller

Beilstein J. Org. Chem. 2024, 20, 787–814, doi:10.3762/bjoc.20.72

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  • deuterium incorporation. However, when D2O-saturated nitromethane was used >95% D-incorporation took place. Hence the small (500–2000 ppm) content of water in commercially available nitromethane was at the origin of the hydrochlorination reaction (Scheme 16). As a result, the reaction of 104 with water
  • the alkene to the corresponding chloride 123 (Scheme 18B). A deuterium label experiment demonstrated the rapid H/D exchange with the deuterated solvent (Scheme 18C). This reaction is synthetically interesting due to the significantly lower cost of AcOD-d4 compared to deuterium-enriched methanesulfonic
  • the higher-substituted carbon atom to furnish intermediate species C. The irreversibility of the hydride addition and the regioselectivity thereof were supported by a deuterium labelling study with PhSiD3. The next steps involve homolytic cleavage of the cobalt–carbon bond to yield a carbon-centered
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Published 15 Apr 2024

Palladium-catalyzed three-component radical-polar crossover carboamination of 1,3-dienes or allenes with diazo esters and amines

  • Geng-Xin Liu,
  • Xiao-Ting Jie,
  • Ge-Jun Niu,
  • Li-Sheng Yang,
  • Xing-Lin Li,
  • Jian Luo and
  • Wen-Hao Hu

Beilstein J. Org. Chem. 2024, 20, 661–671, doi:10.3762/bjoc.20.59

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  • )2 and Xantphos (Scheme 4e). In addition, deuterium labeling experiments were conducted to investigate the H-source of this transformation (for more details, see Supporting Information Information File 1). The isotopic-labeling experiments suggested that both types of protons from the N–H bond of the
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Published 27 Mar 2024

Ligand effects, solvent cooperation, and large kinetic solvent deuterium isotope effects in gold(I)-catalyzed intramolecular alkene hydroamination

  • Ruichen Lan,
  • Brock Yager,
  • Yoonsun Jee,
  • Cynthia S. Day and
  • Amanda C. Jones

Beilstein J. Org. Chem. 2024, 20, 479–496, doi:10.3762/bjoc.20.43

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  • faster with more Lewis basic urea substrates, (3) mixed solvents are uniquely able to enhance rates, with protic methanol and DCM identified as the best combination, and (4) kinetic isotope effects are variable depending on the concentration of protons in solution with small deuterium KIE’s at low
  • undetermined deactivation pathways. A similar 31P spectrum was obtained for the bisphoshine complex of Jackiephos, but in contrast no symmetrical singlet was observed (see Supporting Information File 1, Figure S23). Kinetic deuterium isotope effect Monodeuterated methanol (CH3OD) was tested as an additive on
  • exchange (t < 5 minutes) reduced the N–CH2 doublet (δ 3.84 ppm in CD2Cl2) to a singlet, indicating high incorporation of deuterium into the substrate and corresponding in situ generation of CH3OH. Furthermore, both NH signals appear absent in the 1H NMR spectrum (δ 3.93/3.66). Comparing the rates of
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Published 29 Feb 2024

Synthesis of the 3’-O-sulfated TF antigen with a TEG-N3 linker for glycodendrimersomes preparation to study lectin binding

  • Mark Reihill,
  • Hanyue Ma,
  • Dennis Bengtsson and
  • Stefan Oscarson

Beilstein J. Org. Chem. 2024, 20, 173–180, doi:10.3762/bjoc.20.17

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  • , Reveleris® silica cartiges 40 μm, Büchi Labortechnik AG®) and Biotage® SP4 HPFC (UV 200–500 nm, Biotage® SNAP KP-Sil 50 μm irregular silica, Biotage® AB). Instrumentation 1H NMR and 13C NMR spectra were recorded on Varian Inova spectrometers at 25 °C in chloroform-d (CDCl3), methanol-d4 (CD3OD), deuterium
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Published 30 Jan 2024

Using the phospha-Michael reaction for making phosphonium phenolate zwitterions

  • Matthias R. Steiner,
  • Max Schmallegger,
  • Larissa Donner,
  • Johann A. Hlina,
  • Christoph Marschner,
  • Judith Baumgartner and
  • Christian Slugovc

Beilstein J. Org. Chem. 2024, 20, 41–51, doi:10.3762/bjoc.20.6

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  • of 0.7 equiv of deuterium in the α-position to the cyano group. However, this experiment does not allow for a conclusive distinction between the two postulated hydrogen transfer pathways as the phenolic hydrogen is quickly exchanged for deuterium under these conditions. The evenly strong Michael
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Published 10 Jan 2024

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

  • Karolis Leitonas,
  • Brigita Vigante,
  • Dmytro Volyniuk,
  • Audrius Bucinskas,
  • Pavels Dimitrijevs,
  • Sindija Lapcinska,
  • Pavel Arsenyan and
  • Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

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  • . Photoelectrical and charge-transporting properties The ionization potentials (IPPE) of thin films were obtained by photoelectron emission (PE) spectroscopy in air (Figure 7 and Table 1). To generate photoelectrons detectable by a counter electrode within the PE experiments, a low-power deuterium UV lamp was used
  • , a negative voltage of 300 V was applied to the sample substrate, promoting electron emission from the surface. The photoelectron emission spectra were recorded using a Spectral Products© 30 W deep UV deuterium light source (180–400 nm) ASBN-D130-CM, coupled with the CM110 1/8 m monochromator, which
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Published 12 Dec 2023

α-(Aminomethyl)acrylates as acceptors in radical–polar crossover 1,4-additions of dialkylzincs: insights into enolate formation and trapping

  • Angel Palillero-Cisneros,
  • Paola G. Gordillo-Guerra,
  • Fernando García-Alvarez,
  • Olivier Jackowski,
  • Franck Ferreira,
  • Fabrice Chemla,
  • Joel L. Terán and
  • Alejandro Perez-Luna

Beilstein J. Org. Chem. 2023, 19, 1443–1451, doi:10.3762/bjoc.19.103

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  • . Product 25a is formed on addition of an iPr radical generated by I-atom transfer from iPrI to the Et radical, and is diagnostic for the formation of the latter in the reaction medium. Deuterium labeling experiments were then performed to substantiate the formation of a zinc enolate following radical
  • addition (Scheme 7, bottom). Much to our surprise however, no deuterium incorporation is observed on quenching with ND4Cl/D2O the reaction between 8a and Et2Zn. By contrast, a significant deuterium incorporation is obtained when deuterated starting material (8a-d) is engaged. The combination of these two
  • results is in agreement with the formation of a zinc enolate that undergoes proto- (or deuterio)demetalation with the N–H (or N–D) as proton (or deuterium) source. To further analyze the influence of the presence of an N–H function, we performed other reactions with N-benzyl enoate 10 which proved highly
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Published 21 Sep 2023

Photoredox catalysis enabling decarboxylative radical cyclization of γ,γ-dimethylallyltryptophan (DMAT) derivatives: formal synthesis of 6,7-secoagroclavine

  • Alessio Regni,
  • Francesca Bartoccini and
  • Giovanni Piersanti

Beilstein J. Org. Chem. 2023, 19, 918–927, doi:10.3762/bjoc.19.70

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  • tested the reaction in N,N-dimethylformamide-d7 (DMF-d7), which showed almost quantitative deuterium incorporation. While this result was surprising, further studies into this complex mechanism are ongoing and will be reported in due course. The synthetic potential and utility of this method was further
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Published 26 Jun 2023

Intermediates and shunt products of massiliachelin biosynthesis in Massilia sp. NR 4-1

  • Till Steinmetz,
  • Blaise Kimbadi Lombe and
  • Markus Nett

Beilstein J. Org. Chem. 2023, 19, 909–917, doi:10.3762/bjoc.19.69

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  • molecular formula of C15H18N2O2S (calcd. for C15H19N2O2S, 291.1173) and corresponds to eight degrees of unsaturation. In comparison to the other five molecules compound 6 must contain an even number of nitrogen atoms. The NMR data is comparable to compound 3, but includes a deuterium exchangeable proton
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Published 23 Jun 2023

Pyridine C(sp2)–H bond functionalization under transition-metal and rare earth metal catalysis

  • Haritha Sindhe,
  • Malladi Mounika Reddy,
  • Karthikeyan Rajkumar,
  • Akshay Kamble,
  • Amardeep Singh,
  • Anand Kumar and
  • Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

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  • containing bioactive molecules (Scheme 10). To attain enantioselectivity a chiral phosphine oxide (43)-ligated Ni–Al bimetallic catalyst was used that was critical in improving the reactivity and controlling the selectivity of the reaction. Further, based on deuterium labelling experiments, KIE studies, and
  • of the alkene provides the intermediate 57 which on subsequent reductive elimination furnishes the C4-alkylated products 55. Based on the deuterium exchange experiment, the author suggested that the steps involved in the catalytic cycle from 56A to 57 are reversible in nature, which may activate the
  • with various tethered alkenes, such as 1,1-disubstituted alkenes, styrene, diene, trisubstituted alkene and enamines. To get insights into the mechanism the authors conducted additional experiments including deuterium labelling reactions and proposed the mechanism depicted in Scheme 37b. Initially, the
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Published 12 Jun 2023

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

  • Konstantin Lebedinskiy,
  • Volodymyr Lobaz and
  • Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

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  • with Thermo Scientific Helios γ with wolfram and deuterium lamp. The wavelength range is 190–800 nm. 1H, 13C, and 2D NMR spectra were measured on Bruker Avance III HD 400 spectrometer. For TLC detection of CDs, we charred a TLC plate with 50% sulfuric acid water solution at 250 °C. UV measurements The
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Published 25 Nov 2022

Synthesis of the biologically important dideuterium-labelled adenosine triphosphate analogue ApppI(d2)

  • Petri A. Turhanen

Beilstein J. Org. Chem. 2022, 18, 1466–1470, doi:10.3762/bjoc.18.153

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  • spectrometry. Keywords: ApppI; ATP; deuterium labelling; HPCCC; mevalonate pathway; NMR; synthesis; Introduction It has become clear and evident that phosphonate chemistry plays a crucial role in drug research and development [1][2][3][4]. There are several phosphonate-containing compounds under research or
  • , which was finally confirmed after the tosylation step and purification of compound 4. The signal at 68 ppm with clear carbon–deuterium coupling (1JCD = 22.9 Hz) in the 13C NMR spectrum was unambiguous proof of the doubly deuterated product 4. ApppI(d2) was isolated using two different amounts of TBA
  • deuterium-labelled highly important ATP analogue ApppI(d2) has been described in detail. This leaves the possibility to develop a quantitative MS method for the determination of ApppI in biological samples by using ApppI(d2) as internal standard. Samples of ApppI(d2) are available from the author upon
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Published 14 Oct 2022

Characterization of a new fusicoccane-type diterpene synthase and an associated P450 enzyme

  • Jia-Hua Huang,
  • Jian-Ming Lv,
  • Liang-Yan Xiao,
  • Qian Xu,
  • Fu-Long Lin,
  • Gao-Qian Wang,
  • Guo-Dong Chen,
  • Sheng-Ying Qin,
  • Dan Hu and
  • Hao Gao

Beilstein J. Org. Chem. 2022, 18, 1396–1402, doi:10.3762/bjoc.18.144

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  • with or without addition of deuterated water (D2O). GC–MS analysis showed that when the reaction mixture was supplemented with D2O, the ion peak at m/z 273 was observed, indicating that exogenous deuterium was incorporated into 1 (Supporting Information File 1, Figure S19). This suggests that TadA
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Published 05 Oct 2022

Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies

  • Attila Palágyi,
  • Jindřich Jindřich,
  • Juraj Dian and
  • Sophie Fourmentin

Beilstein J. Org. Chem. 2022, 18, 1346–1354, doi:10.3762/bjoc.18.140

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  • phosphate buffer solutions of pH 1.08, 2.00, 3.00, 4.00, 5.00, 6.00, 7.00, 8.00, 9.00, 10.00 11.00, 12.00, and 12.80 were prepared (see Experimental section) using deuterium oxide instead of water to facilitate NMR spectroscopy experiments. Because of the low solubility of the pro-fragrance in water, it had
  • , 7.00, 8.00, 9.00, 10.00 11.00, 12.00, and 12.80 were prepared by mixing 0.1 M solutions of H3PO4, KH2PO4, K2HPO4, and K3PO4 in ratios given in Table 2 using deuterium oxide instead of distilled water to facilitate NMR spectroscopy experiments. The exact pH value was tuned with titration with the help
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Published 28 Sep 2022

Synthetic strategies for the preparation of γ-phostams: 1,2-azaphospholidine 2-oxides and 1,2-azaphospholine 2-oxides

  • Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 889–915, doi:10.3762/bjoc.18.90

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  • diphenyl-N-benzyl-N-methylphosphinamide (107) in the presence of sec-butyllithium followed by treatment with methanol, deuterium oxide, methyl iodide, and benzaldehyde, affording a series of cyclohexadiene-fused γ-phosphinolactams 108–112 in low regio- and stereoselectivies (Scheme 21) [46]. They further
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Published 22 Jul 2022

Mechanistic studies of the solvolysis of alkanesulfonyl and arenesulfonyl halides

  • Malcolm J. D’Souza and
  • Dennis N. Kevill

Beilstein J. Org. Chem. 2022, 18, 120–132, doi:10.3762/bjoc.18.13

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  • considerable interest because, if the solvolysis is carried out in a deuterated solvent of type ROD in the presence of the conjugate base (OR−), it is found that there is deuterium uptake into the product. This is believed to be excellent evidence for the intermediacy of a sulfene formed by an elimination
  • reaction promoted by the OR− species, with the sulfene then rapidly adding a solvent molecule to give a final product which is identical to the direct substitution product, except that, with the deuterated solvent, deuterium uptake can easily be detected [72][73][74] (Equation 4). This reaction was found
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Published 17 Jan 2022
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