The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives

• Sondos A. J. Almahmoud,
• Joseph Cameron,
• Dylan Wilkinson,
• Michele Cariello,
• Claire Wilson,
• Alan A. Wiles,
• Peter J. Skabara and
• Graeme Cooke

Beilstein J. Org. Chem. 2024, 20, 2921–2930, doi:10.3762/bjoc.20.244

• violanthrone 2b to act as an electron acceptor in OPVs when blended with PDI as a co-acceptor, which showed an enhanced light harvesting and photocurrent generation compared to the device without violanthrone being incorporated (Figure 2) [31]. Liu et al. [32] reported a novel violanthrone derivative 3b via

C–H Trifluoromethylthiolation of aldehyde hydrazones

• Victor Levet,
• Balu Ramesh,
• Congyang Wang and
• Tatiana Besset

Beilstein J. Org. Chem. 2024, 20, 2883–2890, doi:10.3762/bjoc.20.242

• corresponding sulfur-containing heteroarenes, only a few methods have been developed (Scheme 1). In 1988, Lee and co-workers reported the synthesis of SR-containing hydrazones in a two-step process (chlorination [65] then reaction with thiols) from readily available aldehyde-derived hydrazones [66]. Wang et al

• cyclization of aryl hydrazones with aryl isothiocyanates promoted by elemental sulfur [70]. In the course of their studies for the thiocyanation of ketene dithioacetals, Yang, Wang and co-workers developed an electrochemical oxidization-based synthetic strategy to circumvent the need for external oxidants. In

Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions

• Marzieh Norouzi,
• Mohammad Taghi Nazeri,
• Ahmad Shaabani and
• Behrouz Notash

Beilstein J. Org. Chem. 2024, 20, 2870–2882, doi:10.3762/bjoc.20.241

• with 1,10-phenanthroline as cyclic imine under solvent-free conditions for the synthesis of pyrrole-fused phenanthroline. This reaction proceeds via in situ formation of zwitterion I through reaction of the aldehyde and malononitrile followed by 1,3-dipolar cycloaddition (Scheme 1a) [41]. Chen and co

• information All commercially available reagents and chemicals were bought from Merck & Co. and utilized without extra purification. The melting points of all synthesized compounds were measured utilizing an Electrothermal 9200 apparatus. 1H and 13C NMR and spectra in CDCl3 and DMSO-d6 solvents were recorded

N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity

• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2840–2869, doi:10.3762/bjoc.20.240

Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides

• Baptiste Leroux,
• Alexis Beaufils,
• Federico Banchini,
• Olivier Jackowski,
• Alejandro Perez-Luna,
• Fabrice Chemla,
• Marc Presset and
• Erwan Le Gall

Beilstein J. Org. Chem. 2024, 20, 2834–2839, doi:10.3762/bjoc.20.239

• remains tenuous. Indeed, until recently, mixed alkylzinc species were only employed by Carretero and co-workers in related nucleophilic additions to activated imines under Cu catalysis [22]. In 2022, our group demonstrated that alkyl iodides offer a reliable source of heteroleptic organozinc compounds

• through the direct insertion of zinc dust into the C–I bond in acetonitrile at 50 °C [23]. Secondary as well as tertiary organozinc iodides were found to be more reactive than primary ones. Recently, Gaunt and co-workers confirmed this tendency in a related reductive multicomponent procedure involving

Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates

• Kento Iwai,
• Akari Hikasa,
• Kotaro Yoshioka,
• Shinki Tani,
• Kazuto Umezu and
• Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2024, 20, 2827–2833, doi:10.3762/bjoc.20.238

• Department of Chemistry, Faculty of Science, Nara Women’s University, Kitauoyahigashimachi, Nara 630-8506, Japan Kumiai Chemical Industry Co. Ltd., Nakanogo, Fuji, Shizuoka 421-3306, Japan and 5K • I Chemical Industry Co. Ltd., Shinoshinden, Iwata, Shizuoka 437-1213, Japan 10.3762/bjoc.20.238 Abstract The N

• were purchased from commercial sources (Kanto Chemical Co., Inc. or Fujifilm Wako Pure Chemical Corp.) and used without further purification. Super dehydrated, stabilizer-free THF was used as solvent and purchased from Fujifilm Wako Pure Chemical Corp. DEMO was supplied by Kumiai Chemical Industry Co

Investigation of a bimetallic terbium(III)/copper(II) chemosensor for the detection of aqueous hydrogen sulfide

• Parvathy Mini,
• Michael R. Grace,
• Genevieve H. Dennison and
• Kellie L. Tuck

Beilstein J. Org. Chem. 2024, 20, 2818–2826, doi:10.3762/bjoc.20.237

• –guest binding model gave an acceptable fit with low (co)variance of the fit (Table 1). Aqueous buffer HS− studies of [Tb.1·3Cu]3+ The response of [Tb.1·3Cu]3+ to Na2S (HS− in solution at pH 7.4) in both 10 mM HEPES and 10 mM Tris-HCl was investigated. The addition of HS−(aq) ions to a solution of [Tb.1

• the presence of gaseous hydrogen sulfide, the aryl azide is reduced to an aniline functionality and luminescence is restored [11]. Drawing our previous findings and insights from the work of Hou, Wu, and co-workers [21], we postulate that gaseous H2S is interacting with the [Tb.1·3Cu]3+ complex as it

Synthesis and antimycotic activity of new derivatives of imidazo[1,2-a]pyrimidines

• Dmitriy Yu. Vandyshev,
• Daria A. Mangusheva,
• Khidmet S. Shikhaliev,
• Kirill A. Scherbakov,
• Oleg N. Burov,
• Alexander D. Zagrebaev,
• Tatiana N. Khmelevskaya,
• Alexey S. Trenin and
• Fedor I. Zubkov

Beilstein J. Org. Chem. 2024, 20, 2806–2817, doi:10.3762/bjoc.20.236

• , it is worth mentioning the work of Li and co-workers (2011) [20], who described a single example of the formation of such structures by carrying out an organocatalytic domino aza-Michael–Mannich reaction between benzylidene-1H-imidazol-2-amine and cinnamaldehyde. Although the imidazo[1,2-a

Mechanochemical difluoromethylations of ketones

• Jinbo Ke,
• Pit van Bonn and
• Carsten Bolm

Beilstein J. Org. Chem. 2024, 20, 2799–2805, doi:10.3762/bjoc.20.235

• contain a unique structural motif with potential for further functionalizations into highly diverse secondary or tertiary difluoroalkyl ethers. Dolbier and co-workers investigated reactions of difluorocarbene generated from its precursor trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate (TFDA) and

• -depleting sulfur dioxide as side products [46][47]. Later, Ichikawa and co-workers established the release of difluorocarbene from TFDA with catalytic amounts of an N-heterocyclic carbene and a base (Scheme 1C) [29][48][49]. In these reactions, difluoromethyl enol ethers were obtained, which were

• reaction conditions were chosen based on those reported by Ni, Hu and co-workers for the difluoromethylation of alcohols in solution [39]. The two activators KFHF and KOAc were investigated in a dichloromethane/water mixture at room temperature for 10 h. In both cases, the yield of 3a was negligible (with

C–C Coupling in sterically demanding porphyrin environments

• Liam Cribbin,
• Brendan Twamley,
• Nicolae Buga,
• John E. O’ Brien,
• Raphael Bühler,
• Roland A. Fischer and
• Mathias O. Senge

Beilstein J. Org. Chem. 2024, 20, 2784–2798, doi:10.3762/bjoc.20.234

• structural decomposition (NSD) method developed by Shelnutt and co-workers [9] and further implemented and visualized by us [8][10]. Of the four main quantifiable distortion modes, saddle-shaped porphyrins can be afforded by peri-interactions between β-substituents and the meso-substituents [3][11], or

• , many of these strategies are utilized only with planar porphyrins. Apart from the arylation of the β-position of 2,3,5,7,8,10,12,13,15,17,18,20-dodecaarylporphyrins, developed by Smith and co-workers [39] few reports on synthetic techniques for dodecasubstituted nonplanar porphyrins can be found in

• (Table 3, entries 3–5). Increasing the time of reaction, catalyst loading, and equivalents of boronic acid significantly also resulted in no product formation (Table 3, entry 6). Next, a change in the catalyst was investigated, based on a literature procedure which was developed by Johnstone and co

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

• alkoxylation and alkylation products with the assistance of Lewis acid as co-catalyst (Scheme 9). Starting from four different racemic substrates, the same product 6g with 96% ee was obtained under standard conditions. This indicates that the reactions proceed through the same transition state and the

Interaction of a pyrene derivative with cationic [60]fullerene in phospholipid membranes and its effects on photodynamic actions

• Hayato Takagi,
• Çetin Çelik,
• Ryosuke Fukuda,
• Qi Guo,
• Tomohiro Higashino,
• Hiroshi Imahori,
• Yoko Yamakoshi and
• Tatsuya Murakami

Beilstein J. Org. Chem. 2024, 20, 2732–2738, doi:10.3762/bjoc.20.231

• Sciences AG (Farmingdale, NY, USA). FeSO4, DETAPAC and NADH was bought from Sigma-Aldrich (St. Louis, Missouri, USA). DMPO was bought from TCI (Tokyo Chemical Industry Co. Ltd., Tokyo, Japan). Irradiation was performed by blue LED light (464–477 nm, 23 lm·W–1) from Lumiflex300 Pro RGB LED Stripes

Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light

• Francesco Gambuti,
• Jacopo Pizzorno,
• Chiara Lambruschini,
• Renata Riva and
• Lisa Moni

Beilstein J. Org. Chem. 2024, 20, 2722–2731, doi:10.3762/bjoc.20.230

• optimized reaction conditions, we observed good conversion of the starting material, but the desired compound was isolated in very poor yield, as the α-aminoamide 4a resulted the main product (Table 1, entry 1). We were surprised about that, as, even if water is present as co-solvent in the reaction mixture

5th International Symposium on Synthesis and Catalysis (ISySyCat2023)

• Anthony J. Burke and
• Elisabete P. Carreiro

Beilstein J. Org. Chem. 2024, 20, 2704–2707, doi:10.3762/bjoc.20.227

• intramolecular aminocarbonylation using Mo(CO)6. Both catalytic approaches successfully produced the desired DBDAPs. As previously mentioned, organic synthesis is a crucial tool for preparing complex molecules of high value to industry. Frackenpohl et al. [13] designed and synthesized a new library of 2,3

Applications of microscopy and small angle scattering techniques for the characterisation of supramolecular gels

• Connor R. M. MacDonald and
• Emily R. Draper

Beilstein J. Org. Chem. 2024, 20, 2608–2634, doi:10.3762/bjoc.20.220

• use of fluorescence probes should be used in tandem with CLSM. For example, Raeburn et al. showed that the addition of molecular rotors and fluorescent dyes affects the bulk network of self-assembled materials using rheology. The co-packing was observed to alter rheological properties of the materials

• arising, for example, from differences in the rate of fibre growth and entanglements. The change in rheological properties when comparing the material and its co-assembly with the probe shows that addition of such probes may lead to measurements which do not truly represent the system of interest [19

• ]. The work by Alakpa et al. highlights how important it is to consider how one assesses the impact of co-assembly on a molecular system [20]. AFM suggested that the addition of the surfactant-like Fmoc-serine (Fmoc-S) to the fibrous Fmoc-diphenylalanine (Fmoc-FF) did not impact the structure of the Fmoc

Efficient modification of peroxydisulfate oxidation reactions of nitrogen-containing heterocycles 6-methyluracil and pyridine

• Alfiya R. Gimadieva,
• Yuliya Z. Khazimullina,
• Aigiza A. Gilimkhanova and
• Akhat G. Mustafin

Beilstein J. Org. Chem. 2024, 20, 2599–2607, doi:10.3762/bjoc.20.219

• in two different ways: with metallophthalocyanine catalysts present and by including hydrogen peroxide as a co-oxidant (Scheme 1). Metal–phthalocyanine complexes (PcM) are recognized as catalysts for gentle, particular oxidation reactions under aerobic [14] and H2O2-based conditions [15][16][17][18

• − ion, which is formed by the non-radical decomposition of the peroxydisulfate ion in a strongly alkaline medium [34]: The Elbs and Boyland–Sims reactions were also effectively modified by the use of H2O2 as a co-oxidant (binary oxidation mixture APS/H2O2). Adding 2.0–2.3 equiv of H2O2 (Table 3) [35

• LLC, Russia), chloroform (reagent grade, JSC Khimreaktivsnab, Russia) and ethyl alcohol (reagent grade, LLC TD Khimmed, Russia) were used in this work. The phthalocyanine catalysts (Co, FeII, FeIII, Mn, Ni, and Zn phthalocyanines) were synthesized according to the known procedure [44] from

Anion-dependent ion-pairing assemblies of triazatriangulenium cation that interferes with stacking structures

• Yohei Haketa,
• Takuma Matsuda and
• Hiromitsu Maeda

Beilstein J. Org. Chem. 2024, 20, 2567–2576, doi:10.3762/bjoc.20.215

• are the interactions between charged (ionic) π-systems, with interesting electronic properties like electric conductivities. Experimental General procedures Starting materials were purchased from FUJIFILM Wako Pure Chemical Corp., Nacalai Tesque Inc., and Sigma-Aldrich Co. and were used without

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

• benzylic position (Scheme 31). 1.3.2 Co-assisted anodic oxidation. In 2021, Xu and colleagues developed an electrocatalytic approach for the intramolecular oxidative allylic amination and C–H alkylation using cobalt–salen complexes as catalysts [43]. In this reaction, the cobalt catalyst [Co(II)] is first

• oxidized to [Co(III)]+ at the anode, while MeOH undergoes cathodic reduction to form MeO− and H2. The MeO− then deprotonates the carbamate, and the resulting conjugated base is oxidized by the cobalt–salen complex [Co(III)]+, generating an amide radical. This amide radical initiates radical cyclization to

• form a cyclic alkyl radical. The alkyl radical is further oxidized by [Co(III)] to produce the target amination product and a [Co(II)–H] species via direct hydrogen transfer or β-hydride elimination. Deprotonation of [Co(II)–H] by MeO− regenerates the [Co(I)] complex, which is subsequently oxidized

Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols

• Smaher E. Butt,
• Konrad Kepski,
• Jean-Marc Sotiropoulos and
• Wesley J. Moran

Beilstein J. Org. Chem. 2024, 20, 2455–2460, doi:10.3762/bjoc.20.209

• yield (Scheme 1B). Notably, we are unaware of any reported method to achieve this specific transformation in the literature. Although, Tellitu and co-workers have reported a related preparation of indoline derivatives mediated by bis(trifluoroacetoxy)iodobenzene (PIFA) [17]. Results and Discussion In

Homogeneous continuous flow nitration of O-methylisouronium sulfate and its optimization by kinetic modeling

• Jiapeng Guo,
• Weike Su and
• An Su

Beilstein J. Org. Chem. 2024, 20, 2408–2420, doi:10.3762/bjoc.20.205

• serve as guidance for industrial production. Experimental Materials and methods Chemicals O-Methylisouronium sulfate (IO, 95%) was purchased from Shanghai Yien Chemical Technology Co., Ltd; fuming nitric acid (HNO3, 98.0%) was purchased from Sinopharm Chemical Reagent Co., Ltd.; sulfuric acid (H2SO4

• , 98.0%) was purchased from Sinopharm Chemical Reagent Co., Ltd.; pure water from AR, Hangzhou Wahaha Group Co., Ltd.; all reagents were used without further purification. Sulfuric acid solutions of different mass fractions were prepared with pure water and 98% concentrated sulfuric acid in an ice bath

• = 112 mL. Continuous flow microreactor system The continuous flow microreactor system is shown in Figure 1. Solutions A and B were stored in two glass vials (500 mL) with lids and were preheated by two high-pressure PTFE pumps (pump A, pump B, JJRZ-10004F, Hangzhou JingJin Technology Co., Ltd.) and

Evaluating the halogen bonding strength of a iodoloisoxazolium(III) salt

• Dominik L. Reinhard,
• Anna Schmidt,
• Marc Sons,
• Julian Wolf,
• Elric Engelage and
• Stefan M. Huber

Beilstein J. Org. Chem. 2024, 20, 2401–2407, doi:10.3762/bjoc.20.204

• ) Å, 84% of Σr, and C1–I1···Br1 = 176.08(9)°]. The bond distances indicate that the hydrogen bond is noticeably weaker than the two XBs and thus constitutes merely an assisting interaction. The XB interactions in this crystal structure were compared to the ones in the literature-known co-crystal of

Efficient one-step synthesis of diarylacetic acids by electrochemical direct carboxylation of diarylmethanol compounds in DMSO

• Hisanori Senboku and
• Mizuki Hayama

Beilstein J. Org. Chem. 2024, 20, 2392–2400, doi:10.3762/bjoc.20.203

• constant-current electrolysis in DMF using an undivided cell equipped with a Pt cathode and a Mg anode in the presence of carbon dioxide. On the other hand, carboxylation scarcely took place in DMF when other benzyl alcohols were used as substrates. Lundberg and co-workers recently reported similar results

Asymmetric organocatalytic synthesis of chiral homoallylic amines

• Nikolay S. Kondratyev and
• Andrei V. Malkov

Beilstein J. Org. Chem. 2024, 20, 2349–2377, doi:10.3762/bjoc.20.201

• essential to provide a comprehensive overview of this significant topic. Review Asymmetric allylation with boron-based reagents The research on the metal-free, asymmetric organocatalytic allylation of acylimines was pioneered in 2007 by Schaus and co-workers [24]. In their elegant approach, high

• Maraviroc, an HIV-1 drug of the CCR5-receptor antagonists class that was approved by the FDA in 2007. In 2013, a significant work was published by Hoveyda and co-workers [6], who demonstrated that small organic molecules like hindered aminophenol 11 can serve as highly efficient and versatile catalysts in

• for the resolution of chiral amines [28]. However, it was not until 2004 that they were recognised as efficient chiral Brønsted acid organocatalysts for asymmetric Mannich reactions [29]. Malkov and co-workers revealed [30] that (R)-TRIP can act as a very efficient catalyst for the kinetic resolution

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

• (AS-MS), co-fractionation mass spectrometry (CF-MS), or mass spectrometry integrated with equilibrium dialysis for the discovery of allostery systematically (MIDAS) [38][39][40][41][42][43][44]. The chemical proteomics approach and related activity-based protein profiling has been reviewed

Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis

• Stefan P. Schmid,
• Leon Schlosser,
• Frank Glorius and
• Kjell Jorner

Beilstein J. Org. Chem. 2024, 20, 2280–2304, doi:10.3762/bjoc.20.196

• Drawing inspiration from linear free energy relationships, MLR models, pioneered by Norrby and co-workers [83] and later further developed by Sigman and co-workers [69][82], are commonly used for the prediction of enantioselectivity. In such models, the substrates, catalysts, and other relevant reaction

• structure, it is important to include information from relevant conformers. To avoid losing important information from discarding conformers, Paton and co-workers [85] introduced wSterimol, which takes into account structures from the entire conformer ensemble via Boltzmann-weighting. The authors used their

• acrylates [95] and found a similar performance compared to NCI probe descriptors. Despite the success of this approach, it is important to remember that descriptors do not have to be parameters of one molecule and that intermolecular terms can be used to derive mechanistic hypotheses. Toste and co-workers