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Search for "sulfone" in Full Text gives 115 result(s) in Beilstein Journal of Organic Chemistry.

Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents

  • Jiangfei Chen,
  • Yi-Lin Qu,
  • Ming Yuan,
  • Xiang-Mei Wu,
  • Heng-Pei Jiang,
  • Ying Fu and
  • Shengrong Guo

Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98

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  • oxidation, ultimately forming the final oxindole product 76a. Interestingly, the reaction proceeds via two distinct pathways depending on the presence of an alkene radical acceptor, with DMSO or dimethyl sulfone as the byproduct. In addition to transition-metal and photocatalyzed systems, several metal-free
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Published 24 Jun 2025

Synthetic approach to borrelidin fragments: focus on key intermediates

  • Yudhi Dwi Kurniawan,
  • Zetryana Puteri Tachrim,
  • Teni Ernawati,
  • Faris Hermawan,
  • Ima Nurasiyah and
  • Muhammad Alfin Sulmantara

Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91

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  • approach for constructing Morken’s C2–C12 fragment In 2019, Uguen and co-workers introduced a strategy to assemble Morken’s C2–C12 intermediate 20 [41]. Their approach utilized iterative base-catalyzed condensation of sulfone compounds with epoxides. As illustrated in Scheme 1, the monoalcohol 20 was
  • prepared via PMB removal of compound 21, which, in turn, was obtained through desulfonylation of compound 22. Compound 22 originated from the condensation of epoxide 23a with sulfone 26, which was produced by desilylation of 25 followed by converting the resulting primary alcohol into a sulfone group
  • . Intermediate 25 was prepared through TBDMS protection and desulfonylation of 24, itself derived from the condensation of epoxide 23b and sulfone 27. The precursor 27 was synthesized from Roche ester 29 via a sequence of steps, including reduction, three-carbon homologation, and enzymatic desymmetrization. An
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Published 12 Jun 2025

Biobased carbon dots as photoreductants – an investigation by using triarylsulfonium salts

  • Valentina Benazzi,
  • Arianna Bini,
  • Ilaria Bertuol,
  • Mariangela Novello,
  • Federica Baldi,
  • Matteo Hoch,
  • Alvise Perosa and
  • Stefano Protti

Beilstein J. Org. Chem. 2025, 21, 1024–1030, doi:10.3762/bjoc.21.84

Graphical Abstract
  • material was observed, thus pointing out the key role of CDs in the process. Some additional irradiation was carried out to identify the aryl radical released during the irradiation. Unfortunately, when the reaction was conducted in the presence of both furan and allyl phenyl sulfone [27] no arylation
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Published 26 May 2025

Study of tribenzo[b,d,f]azepine as donor in D–A photocatalysts

  • Katy Medrano-Uribe,
  • Jorge Humbrías-Martín and
  • Luca Dell’Amico

Beilstein J. Org. Chem. 2025, 21, 935–944, doi:10.3762/bjoc.21.76

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  • : diphenyl sulfone (4), dibenzo[b,d]thiophene 5,5-dioxide (5), and 9,9-dimethyl-9H-thioxanthene 10,10-dioxide (6). The selection of these scaffolds was aimed at investigating the effect of conjugation and rigidity/flexibility on the presence of the same donor (TBA, a). In the case of the D–A compounds 4a and
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Published 14 May 2025

Origami with small molecules: exploiting the C–F bond as a conformational tool

  • Patrick Ryan,
  • Ramsha Iftikhar and
  • Luke Hunter

Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54

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Published 02 Apr 2025

Formaldehyde surrogates in multicomponent reactions

  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

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  • this case, the mechanism appears to proceed through the formation of free radical species, where APS plays the role of oxidant and radical activator of DMSO, generating reactive radical species of DMSO or dimethyl sulfone that react with the nitrogen of saccharine compound 19 without the need for a
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Published 13 Mar 2025

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

  • Francesco Mele,
  • Ana M. Constantin,
  • Andrea Porcheddu,
  • Raimondo Maggi,
  • Giovanni Maestri,
  • Nicola Della Ca’ and
  • Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

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  • (12.3, 0.2 mmol), tosyl chloride (12.4, 2 equiv), and tris(4-methoxyphenyl)amine (10 mol %) was milled in the presence of 100 wt % of SAOED at 30 Hz for 3 h, sulfone 12.5 was obtained in 89% yield after isolation. The synthesis of 12.5 was scaled up to 15 mmol scale, obtaining the desired product in a
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Published 03 Mar 2025

Synthesis of new condensed naphthoquinone, pyran and pyrimidine furancarboxylates

  • Kirill A. Gomonov,
  • Vasilii V. Pelipko,
  • Igor A. Litvinov,
  • Ilya A. Pilipenko,
  • Anna M. Stepanova,
  • Nikolai A. Lapatin,
  • Ruslan I. Baichurin and
  • Sergei V. Makarenko

Beilstein J. Org. Chem. 2025, 21, 340–347, doi:10.3762/bjoc.21.24

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  • furopyran, furocoumarin [9][10], and furopyrimidine series [11][12]. It is known that the main approaches to the synthesis of naphtho[2,3-b]furan-4,9-diones are reactions of hydroxynaphthalene-1,4-dione with ethane-1,2-diol [13], chloroacetaldehyde [14], ethenyl methyl sulfone [15], or ethenyl acetate [16
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Published 12 Feb 2025

Synthesis of disulfides and 3-sulfenylchromones from sodium sulfinates catalyzed by TBAI

  • Zhenlei Zhang,
  • Ying Wang,
  • Xingxing Pan,
  • Manqi Zhang,
  • Wei Zhao,
  • Meng Li and
  • Hao Zhang

Beilstein J. Org. Chem. 2025, 21, 253–261, doi:10.3762/bjoc.21.17

Graphical Abstract
  • which the thiosulfonate was cleaved and then dimerized to form the disulfide. The reaction of sodium p-toluenesulfinate and styrene resulted in the generation of the corresponding vinyl sulfone (Scheme 5, reaction 2), suggesting the formation of p-toluenesulfonyl iodide during the reaction [50][51
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Published 03 Feb 2025

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

  • Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

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  • different electronic properties (18, 25–41, Figure 6) were screened as catalysts for the sulfa-Michael addition of tert-butyl benzylmercaptan 42 to phenyl vinyl sulfone (43). Without the addition of a porphyrin, no product was formed. Among the non-alkylated porphyrins (18, 25–32) only the ones containing
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Published 27 Nov 2024

Advances in radical peroxidation with hydroperoxides

  • Oleg V. Bityukov,
  • Pavel Yu. Serdyuchenko,
  • Andrey S. Kirillov,
  • Gennady I. Nikishin,
  • Vera A. Vil’ and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2024, 20, 2959–3006, doi:10.3762/bjoc.20.249

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Published 18 Nov 2024

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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  • ). Further control experiments and DFT calculations show that during the catalytic process, tertiary amine directly participates as a nucleophilic reagent to give the ammonium salt, which then releases dimethylaminium to provide the final product (Scheme 12). Chiral allylic sulfone compounds can be easily
  • -, stereo-, and enantioselectivities, resulting in a series of chiral yne-allylic sulfone compounds with different substituents (Scheme 13, 14a–q). Due to the high steric hindrance of the γ-site, nucleophilic substitutions preferentially occur at the α-site. Through subsequent control experiments, they
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Published 31 Oct 2024

O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization

  • Kateryna V. Dil and
  • Vitalii A. Palchykov

Beilstein J. Org. Chem. 2024, 20, 2143–2151, doi:10.3762/bjoc.20.184

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  • obtained products are characterized by the following signals: aromatic ring protons (6.25–8.23 ppm), Ar–CH group proton singlet (5.13–5.44 ppm), broadened NH singlets (7.78–10.89 ppm), as well as the corresponding signals of successive 3 × CH2 groups of the sulfone fragment (2.18–3.34 ppm). Such a set of
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Published 27 Aug 2024

Regioselective quinazoline C2 modifications through the azide–tetrazole tautomeric equilibrium

  • Dāgs Dāvis Līpiņš,
  • Andris Jeminejs,
  • Una Ušacka,
  • Anatoly Mishnev,
  • Māris Turks and
  • Irina Novosjolova

Beilstein J. Org. Chem. 2024, 20, 675–683, doi:10.3762/bjoc.20.61

Graphical Abstract
  • substrates, but the step sulfoxide → sulfone was entirely slower and required stirring overnight (except for 8d (R = iC3H7)). With 2-chloro-6,7-dimethoxy-4-sulfonylquinazolines 8 in hand, we started to explore the reactivity in SNAr reactions (Scheme 5). Sulfonyl group dance reactions did not work in
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Published 28 Mar 2024

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

  • Periklis X. Kolagkis,
  • Eirini M. Galathri and
  • Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

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Published 22 Feb 2024

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

  • Aissam Okba,
  • Pablo Simón Marqués,
  • Kyohei Matsuo,
  • Naoki Aratani,
  • Hiroko Yamada,
  • Gwénaël Rapenne and
  • Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

Graphical Abstract
  • , were synthesized as direct soluble precursors of PBIs 6a,b, along with the corresponding oxides, namely sulfoxides 4a,b and sulfone 5 (Scheme 4). An X-ray crystal structure of the extended thiepine 3b confirmed its bent structure, with a protrusion of the sulfur atom out of the π-surface (Figure 1). As
  • perylene moiety was next tested upon different stimuli, such as electron injection, thermal activation and photoirradiation. Importantly, the dinaphthothiepine S,S-dioxide, i.e., the sulfone soluble precursor 5, failed to deliver PBI whatever the activation mode (Scheme 4, bottom). For dinaphthothiepine 3
  • selective oxidation of thiepine and selenepine to give rise to the corresponding sulfoxide 29b, selenoxide 29c and sulfone 30b in excellent yields. All the prepared chalcogen-doped HBC derivatives exhibit good solubility in organic solvents, in line with their highly distorted saddle-shaped or helical
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Published 15 Feb 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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  • University of Technology, Stremayrgasse 9, 8010 Graz, Austria 10.3762/bjoc.20.6 Abstract The reactions of 2,4-di-tert-butyl-6-(diphenylphosphino)phenol and various Michael acceptors (acrylonitrile, acrylamide, methyl vinyl ketone, several acrylates, methyl vinyl sulfone) yield the respective phosphonium
  • carbanion [13][14]. Also with other Michael acceptors such as methyl vinyl ketone, several acrylates as well as methyl vinyl sulfone the reaction proceeds smoothly under the same reaction conditions (Scheme 1). Conversions of 1 are usually quantitative within 24 h and all phosphonium phenolates can be
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Published 10 Jan 2024

Anion–π catalysis on carbon allotropes

  • M. Ángeles Gutiérrez López,
  • Mei-Ling Tan,
  • Giacomo Renno,
  • Augustina Jozeliūnaitė,
  • J. Jonathan Nué-Martinez,
  • Javier Lopez-Andarias,
  • Naomi Sakai and
  • Stefan Matile

Beilstein J. Org. Chem. 2023, 19, 1881–1894, doi:10.3762/bjoc.19.140

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  • below that of unsubstituted NDIs despite stronger π acidity. Supported by experimental and computational data, this poor performance of dyad 46 was explained by lone-pair π interactions of the fullerene with the donating oxygens. These lone-pair π interactions were even more impactful on the sulfone
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Published 12 Dec 2023

Radical chemistry in polymer science: an overview and recent advances

  • Zixiao Wang,
  • Feichen Cui,
  • Yang Sui and
  • Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

Graphical Abstract
  • by radical unzipping depolymerization under photon or β-irradiation (Scheme 20a). Similarly, poly(olefin sulfone) undergoes depolymerization upon irradiation of light or electron beams [193][194]. It is an alternating copolymer of 1-olefins and SO2, and therefore the decomposition products are mostly
  • gaseous [195]. While the depolymerization in both systems has a thermodynamic origin [196], the mechanism of poly(olefin sulfone) depolymerization is much more complex. Bowmer et al. proposed a simultaneous radical/cationic process (Scheme 20b) [197]. Meanwhile, an anionic process is also possible in the
  • using benzophenone. Depolymerization mechanism of common photoresists. (a) A possible mechanism of radiation decomposition of poly(methyl methacrylate). (b) A proposed mechanism of simultaneous radical/cationic decomposition of poly(olefin sulfone) upon radiation [197]. Proposed mechanisms of
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Published 18 Oct 2023

Synthesis of ether lipids: natural compounds and analogues

  • Marco Antônio G. B. Gomes,
  • Alicia Bauduin,
  • Chloé Le Roux,
  • Romain Fouinneteau,
  • Wilfried Berthe,
  • Mathieu Berchel,
  • Hélène Couthon and
  • Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

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  • has similar cell toxicity than edelfosine-C18 on HL-60 leukemic cells [129][130]. The authors also reported that the sulfone 26.5 (Figure 26B) had similar cytotoxicity than edelfosine-C18. In 1987, the group of E. J. Modest reported that the thioether 26.4 featured comparable cytotoxicity than C18
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Published 08 Sep 2023

Selective and scalable oxygenation of heteroatoms using the elements of nature: air, water, and light

  • Damiano Diprima,
  • Hannes Gemoets,
  • Stefano Bonciolini and
  • Koen Van Aken

Beilstein J. Org. Chem. 2023, 19, 1146–1154, doi:10.3762/bjoc.19.82

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  • in only 20% conversion after 60 minutes. Salts Both LiCl and NaCl induced a strong rate acceleration, resulting in (near) full conversion within only 20 minutes (Figure 1B). With LiCl the selectivity was maintained while the presence of NaCl leads to a decrease in selectivity due to sulfone formation
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Published 31 Jul 2023

Photoredox catalysis harvesting multiple photon or electrochemical energies

  • Mattia Lepori,
  • Simon Schmid and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

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Published 28 Jul 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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  • formation and a hydroxyl radical (•OH). However, it is possible to transform an alcohol into a leaving group, in the radical sense, by converting it into a halide or pseudohalide derivative [104][105]. For alcohol 8, all attempts to make a better leaving group, including phenyl sulfone derivative, to have
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Published 26 Jun 2023

Construction of hexabenzocoronene-based chiral nanographenes

  • Ranran Li,
  • Di Wang,
  • Shengtao Li and
  • Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

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  • this [7]helicene family by introducing different linkers such as nitrogen, sulfur, sulfone, ketone, methylene, and derivatives of ketone [44]. Due to the varied nature of the different linkers, the photophysical and semiconductor properties can be effectively tuned. Feng and co-workers reported a
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Published 30 May 2023

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

  • Péter Kisszékelyi and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

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  • , we have investigated the domino reaction of the formed metal enolates with activated alkenes 91 [59]. Alkenes with two activating groups were needed for efficient enolate-trapping reactions, sulfone or phosphonate activating groups being the most suitable ones (Scheme 23). Harutyunyan and co-workers
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Published 04 May 2023
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