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Search for "acid" in Full Text gives 2968 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

N-Salicyl-amino acid derivatives with antiparasitic activity from Pseudomonas sp. UIAU-6B

  • Joy E. Rajakulendran,
  • Emmanuel Tope Oluwabusola,
  • Michela Cerone,
  • Terry K. Smith,
  • Olusoji O. Adebisi,
  • Adefolalu Adedotun,
  • Gagan Preet,
  • Sylvia Soldatou,
  • Hai Deng,
  • Rainer Ebel and
  • Marcel Jaspars

Beilstein J. Org. Chem. 2025, 21, 1388–1396, doi:10.3762/bjoc.21.103

Graphical Abstract
  • new natural products, pseudomonins D–G (1–4) isolated alongside other three known compounds, pseudomonine (5), pseudomonin B (6) and salicylic acid (7), were elucidated based on high-resolution mass spectrometry, 1D and 2D NMR analyses. The absolute configurations of the threonine residue in compounds
  • (3 and 4) isolated alongside three known compounds, pseudomonine (5), pseudomonin B (6) and salicylic acid (7) [15] from the Pseudomonas sp. UIAU-6B strain by altering the fermentation conditions using an open system shaker at room temperature [16][17][18]. Results and Discussion The bacterial strain
  • 1,2-disubstituted benzene ring system was identified by the 1H NMR spectrum showing downfield methine protons at δH 7.88 (dd, J = 8.0, 1.5 Hz, H-5), 7.37 (td, J = 8.0, 1.5 Hz, H-3) 7.01 (d, J = 8.0 Hz, H-2) and 6.92 (t, J = 8.0, H-4) that were consistent with a salicylic acid unit. This was supported
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Published 04 Jul 2025

High-pressure activation for the solvent- and catalyst-free syntheses of heterocycles, pharmaceuticals and esters

  • Kelsey Plasse,
  • Valerie Wright,
  • Guoshu Xie,
  • R. Bernadett Vlocskó,
  • Alexander Lazarev and
  • Béla Török

Beilstein J. Org. Chem. 2025, 21, 1374–1387, doi:10.3762/bjoc.21.102

Graphical Abstract
  • hydrostatic pressure (HHP) was found to be an efficient activation method in several catalyst- and solvent-free reactions and has found application for the syntheses of heterocycles and the preparation of active pharmaceutical ingredients (APIs) via acylation and acid- and solvent-free esterification. The
  • -products. A computational study accompanies the experimental data to interpret the outcome of the reactions. Keywords: acetaminophen; acetylsalicylic acid; benzimidazoles; catalyst-free synthesis; cyclization; esters; high hydrostatic pressure; pyrazoles; Introduction Non-traditional activation methods
  • of important heterocycles, the synthesis of well-known APIs, such as acetaminophen and acetylsalicylic acid, a variety of esterification reactions and the successful scale up (up to 100 g scale) of the Paal–Knorr reaction. The use of HHP appears to provide several advantages, for example, resulting
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Published 02 Jul 2025

Oxetanes: formation, reactivity and total syntheses of natural products

  • Peter Gabko,
  • Martin Kalník and
  • Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

Graphical Abstract
  • from esters of functionalised arylacetic acid 5 or 6 and involves two separate protocols: first, a metallacarbene, which undergoes the insertion, is generated from the corresponding diazo precursor formed either in flow via hydrazone oxidation (PS-TsNIK packed column), or in batch mode via diazo
  • chlorides (Scheme 11a) [44]. The authors found that the secondary alcohol precursors were less reactive and that best results were obtained at low temperature (≤−50 °C) and in chlorinated solvents. The synthesis of these cages was later revisited by Le Drian et al. in 2011 who studied a Lewis acid-catalysed
  • epoxide-opening cyclisation for the oxetane formation (Scheme 11b) [45]. The highest yield was obtained for the PhSH/I2 10:1 activator under unusually mild conditions – the authors believed it is due to the oxa-bridge which facilitates the Lewis acid coordination. In 2001, Rousseau and colleagues reported
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Published 27 Jun 2025

Recent advances and future challenges in the bottom-up synthesis of azulene-embedded nanographenes

  • Bartłomiej Pigulski

Beilstein J. Org. Chem. 2025, 21, 1272–1305, doi:10.3762/bjoc.21.99

Graphical Abstract
  • in 1,2-dichloroethane giving PAHs 134–137 in high yields (71–85%). All the new PAHs exhibit characteristics typical for “true” π-extended azulenes, such as azulene-like optical absorption and narrow HOMO–LUMO gaps. In addition, compounds 134–137 show reversible stimuli-responsiveness against the acid
  • , new OFET-based acid vapor sensors were developed from 150 by synergistically utilizing its charge transport and protonation−deprotonation properties. The solution-phase synthesis of a non-benzenoid nanoribbon from an azulene-containing polymer via alkyne benzannulation was reported by Morin and co
  • -workers (Scheme 20) [98]. The starting polymer 152 was synthesized using Suzuki cross coupling and is regiorandom, meaning the orientation of the azulene units within the main chain is not defined. Polymer 152 was annulated using MsOH (methanesulfonic acid) yielding the non-alternant graphene nanoribbon
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Published 26 Jun 2025

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

Graphical Abstract
  • activated alkenes involving benzylic C(sp3)–H bonds through a cascade cyclization process (Scheme 1) [2]. This organomediated approach can be facilitated by a catalytic amount of Lewis acid. Using DTBP as the oxidant and IrCl3 as the promoter, a range of benzylic C–H bonds in arylmethanes
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Published 24 Jun 2025

Optimized synthesis of aroyl-S,N-ketene acetals by omission of solubilizing alcohol cosolvents

  • Julius Krenzer and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2025, 21, 1201–1206, doi:10.3762/bjoc.21.97

Graphical Abstract
  • presumed byproducts in the addition–elimination sequence in the presence of an excess of ethanol as a cosolvent are the ethyl ester formed by Einhorn acylation [7] of the acid chloride under the standard conditions and deep colored polar byproducts (according to TLC detection) that arise from self
  • -condensation of 2-methylbenzothiazolium salts 7 and intermediary formed S,N-ketene acetals 4 at elevated temperatures. Einhorn acylation is governed by the electrophilicity of the acid chloride or acylammonium species and the nucleophilicity of any nucleophilic species present in the reaction mixture. In
  • dichloromethane; N = 17.10 in acetonitrile) [14] than ethanol or the S,N-ketene acetal intermediate 4. Hence, mechanistically the acid chloride first transforms to an acylammonium species as in Einhorn acylations [7]. As a consequence, for avoiding any competing ethyl ester formation, ethanol has to be omitted
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Published 20 Jun 2025

Synthesis of β-ketophosphonates through aerobic copper(II)-mediated phosphorylation of enol acetates

  • Alexander S. Budnikov,
  • Igor B. Krylov,
  • Fedor K. Monin,
  • Valentina M. Merkulova,
  • Alexey I. Ilovaisky,
  • Liu Yan,
  • Bing Yu and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2025, 21, 1192–1200, doi:10.3762/bjoc.21.96

Graphical Abstract
  • effective generation of phosphorous radicals. Under a pure O2 atmosphere, the interception of formed P-centered radicals by excess oxygen can presumably inhibit the target process by the formation of unreactive phosphoric acid from the corresponding H-phosphonate [73][74]. The formation of phosphoric acid
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Published 20 Jun 2025

Selective monoformylation of naphthalene-fused propellanes for methylene-alternating copolymers

  • Kenichi Kato,
  • Tatsuki Hiroi,
  • Seina Okada,
  • Shunsuke Ohtani and
  • Tomoki Ogoshi

Beilstein J. Org. Chem. 2025, 21, 1183–1191, doi:10.3762/bjoc.21.95

Graphical Abstract
  • followed by acid-mediated condensation. The linear copolymers show good solubility and carbon dioxide adsorption. Keywords: alternating copolymer; building block; formylation; gas adsorption; propellane; Introduction Combination of sp2- and sp3-hybridized atoms in core π-skeletons [1][2][3] is a key to
  • -fused propellanes simply by reduction into the corresponding alcohols followed by acid-mediated Friedel–Crafts-type reactions (Figure 2a and Figure S201 in Supporting Information File 1) [67][68]. Reduction by NaBH4 proceeded well for both monoaldehydes [4.3.3]_CHO and [3.3.3]_CHO resulting in over 90
  • % yield. Alcohol products, [4.3.3]_CH2OH and [3.3.3]_CH2OH, were then tested in acidic conditions using anhydrous FeCl3 as a Lewis acid. After the reactions, the alcohol proton signals at 1.54–1.58 ppm disappeared in the 1H NMR spectra, and aliphatic carbon ones at 63.1–63.2 ppm were largely up-field
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Published 18 Jun 2025

Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C–H activation with directing groups

  • Julius Seumer,
  • Nicolai Ree and
  • Jan H. Jensen

Beilstein J. Org. Chem. 2025, 21, 1171–1182, doi:10.3762/bjoc.21.94

Graphical Abstract
  • and carboxylic acid. The palladacycle intermediate can undergo further (coupling) reactions and form a variety of products via reductive elimination. In previous studies, the rate- and regioselectivity-controlling step was identified as the formation of the palladacycle [5][6][7]. The regioselectivity
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Published 16 Jun 2025

A multicomponent reaction-initiated synthesis of imidazopyridine-fused isoquinolinones

  • Ashutosh Nath,
  • John Mark Awad and
  • Wei Zhang

Beilstein J. Org. Chem. 2025, 21, 1161–1169, doi:10.3762/bjoc.21.92

Graphical Abstract
  • initial GBB reaction of aminopyridines 1 (0.5 mmol), isocyanides 3 (1.2 equiv), and furfuraldehydes 2 (1.2 equiv) was conducted in 3:1 CH2Cl2/MeOH (4 mL) using Yb(OTf)3 (0.08 equiv) as a Lewis acid catalyst under microwave irradiation at 100 °C for 1 h (Scheme 2). Nineteen distinct adducts 4 were obtained
  • tested, AlCl₃ gave the best result, while CuCl, ZnCl2, PdCl2 and Sc(OTf)3 showed moderate conversions (30–55%), and InCl3 had the lowest efficiency. Without any Lewis acid we observed no conversion by LC–MS (Table 1, entry 16). During the reaction, IMDA adduct 7a was detected by LC–MS (Figure S1
  • GBB reactions for the preparation of imidazo[1,2-a]pyridines 4 were conducted using aminopyridines 1 (0.5 mmol), isocyanides 3 (0.6 mmol, 1.2 equiv), and furfuraldehyde 2 (0.6 mmol, 1.2 equiv) in 3:1 DCM/MeOH (4 mL) with Yb(OTf)3 (0.04 mmol, 0.08 equiv) as a Lewis acid catalyst under microwave
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Published 13 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

Graphical Abstract
  • synthesis of polydeoxypropionate based on iridium-catalyzed asymmetric hydrogenation of α-substituted acrylic acid [40]. This method was subsequently applied to the synthesis of a promising vaccine candidate (+)-phthioceranic acid, as well as key intermediates for two natural products, ionomycin and
  • borrelidin (C3–C11). The synthesis involved three main steps: (1) carboxymethylation using Meldrum’s acid, (2) alkenylation with Eschenmoser’s salt, and (3) asymmetric hydrogenation catalyzed by iridium complex (Ra)-50 or (Sa)-50. The authors began their investigation by performing the hydrogenation of α
  • -substituted acrylic acid 51 (Scheme 7). After optimization, the iridium complex (Ra)-50, in the presence of cesium carbonate, was identified as the most efficient catalyst, producing compound 52 in 97% yield with an enantiomeric excess of 97.6%. Subsequently, compound 52 was treated with Meldrum’s acid in the
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Published 12 Jun 2025

Gold extraction at the molecular level using α- and β-cyclodextrins

  • Susana Santos Braga

Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89

Graphical Abstract
  • precious metals [42]. The process of gold precipitation with cyclodextrins, bromic acid and potassium hydroxide to form the potassium bromoaurate salt was patented, with patent coverage expanding to metals like silver, platinum, palladium, and rare earths, as well as the use of other cyclodextrins, β- and
  • γ-CDs, other acids (including hydrogen halides, nitric acid, sulfuric acid, and mixtures thereof) and sodium hydroxide (instead of potassium hydroxide) [43]. Scale-up pilot trials on 20 batch samples were conducted in Arizona with partnership from companies already active in the market. Results
  • [45]. The ores were obtained in an artisanal way from the Shanono gold deposit in Kano State, Nigeria. The researchers involved in this study used a modified aqua regia solution to digest the ore concentrate, in which hydrochloric acid was replaced by hydrobromic acid. Upon addition of α-CD and KOH
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Published 06 Jun 2025

A versatile route towards 6-arylpipecolic acids

  • Erich Gebel,
  • Cornelia Göcke,
  • Carolin Gruner and
  • Norbert Sewald

Beilstein J. Org. Chem. 2025, 21, 1104–1115, doi:10.3762/bjoc.21.88

Graphical Abstract
  • Erich Gebel Cornelia Gocke Carolin Gruner Norbert Sewald Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, Universitätsstraße 25, D-33615 Bielefeld, Germany 10.3762/bjoc.21.88 Abstract Pipecolic acid is known as a non-proteinogenic amino acid with a secondary amine
  • . It contains a six-membered ring and is, like its five-membered correlate, known for its secondary structure inducing properties, which are particularly useful in the design of peptide conformations. We present a new and improved way to generate enantiomerically pure pipecolic acid derivatives with
  • aryl modifications in C6 position by utilising the chiral pool of a non-proteinogenic amino acid in combination with transition metal-catalysed cross-coupling reactions. Moreover, we present an in-depth NMR analysis of the key intermediate steps, which illustrates the conformational constraints in
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Published 04 Jun 2025

Supramolecular assembly of hypervalent iodine macrocycles and alkali metals

  • Krishna Pandey,
  • Lucas X. Orton,
  • Grayson Venus,
  • Waseem A. Hussain,
  • Toby Woods,
  • Lichang Wang and
  • Kyle N. Plunkett

Beilstein J. Org. Chem. 2025, 21, 1095–1103, doi:10.3762/bjoc.21.87

Graphical Abstract
  • . Results and Discussion We have reported the synthesis of several variations of valine and phenylalanine-based HIMs that are based on benzene-, naphthalene-, and anthraquinone systems [18][19]. This study employed a phenylalanine and iodobenzoic acid-based HIM system owing to its simplicity in synthesis
  • and ease of crystal growth. Following our previously established synthetic route [18], phenylalanine-based HIM 1 was synthesized in three steps by utilizing commercially available 2-iodobenzoic acid and ʟ-Phe-Ot-Bu as starting materials (Supporting Information File 1). Phenylalanine HIM 1 was
  • macrocycle is electrophilic in nature. In addition, DFT results show the three outwardly projected carbonyl oxygens (formerly the carbonyl of benzoic acid) are negatively charged and can potentially bind or interact with metal cations. Figure 3 (right) shows the calculated electrostatic potential map with
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Published 30 May 2025

Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

  • Betty A. Kustiana,
  • Galuh Widiyarti and
  • Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

Graphical Abstract
  • Cinnamic acid derivatives represent a significant class of biologically active compounds exhibiting a broad spectrum of activities, such as antifungal, antidengue, antimetastatic, antimicrobial, antibacterial, and anticancer properties. Their preparation has attracted considerable attention due to their
  • versatile applications across the pharmaceutical, food, and chemical sectors. This review elucidates the functional groups of cinnamic acid that are instrumental in the rational design of biologically active derivatives. A comprehensive representative of recent advancements in synthetic methodologies over
  • the past five years is presented, particularly emphasizing the active scaffolds of bioactive cinnamic acid derivatives. The review provides a strategic overview of alternative synthetic routes and highlights the latest innovations, including more efficient, highly selective, and environmentally
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Published 28 May 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
  • different organic sources as photoreductants. Such carbon nanomaterials were synthesized by two different approaches, either hydrothermal or pyrolytic, from citric acid and glucose as the starting organic substrates. On the other hand, carbon dots deriving from fishery waste (bass scales) and fruit
  • efficiency of the resulting CDs. In this context, citric acid-derived materials (both graphitic and amorphous) were found as the most promising materials, while less satisfactory results have been observed when using CDs derived from glucose and biowastes. Keywords: agricultural waste; carbon dots (CDs
  • have been considered as a promising source of aryl radicals and employed in organic synthesis [20][21][22][23][26][27][28][29][30][31][32]. This investigation aims to compare the performance of CDs prepared from several carbon precursors including citric acid, glucose, and organic waste materials via
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Published 26 May 2025

Recent total synthesis of natural products leveraging a strategy of enamide cyclization

  • Chun-Yu Mi,
  • Jia-Yuan Zhai and
  • Xiao-Ming Zhang

Beilstein J. Org. Chem. 2025, 21, 999–1009, doi:10.3762/bjoc.21.81

Graphical Abstract
  • quaternary center in a single step. As depicted in Scheme 1, key enamide 1 was prepared from (R)-pulegone in 6 steps. In the presence of the weak acid H3PO4, protonation of 1 generates a stabilized iminium ion 2, which then undergoes a 6-exo-trig cyclization to deliver 4 after hydration of cation 3. Notably
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Published 22 May 2025

On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals

  • Daniel Straub,
  • Markus Gross,
  • Mona E. Arnold,
  • Julia Zolg and
  • Alexander J. C. Kuehne

Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80

Graphical Abstract
  • to be altered sufficiently to evoke a noticeable improvement of the ϕ [48]. This also holds true for mono-para-substitution with boronic acid derivatives, yielding λem = 580 nm and ϕ of 1–3% (in dichloromethane) [49]. Substituting one or two of the 2,4,6-trichlorinated rings in TTM with 2,4,6
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Published 21 May 2025

Studies on the syntheses of β-carboline alkaloids brevicarine and brevicolline

  • Benedek Batizi,
  • Patrik Pollák,
  • András Dancsó,
  • Péter Keglevich,
  • Gyula Simig,
  • Balázs Volk and
  • Mátyás Milen

Beilstein J. Org. Chem. 2025, 21, 955–963, doi:10.3762/bjoc.21.79

Graphical Abstract
  • 21 under extremely harsh conditions (100 °C, 130 bar), followed by N-acetylation gave a mixture of diastereomeric racemates 22, which was cyclized to a diastereomeric mixture of β-carboline derivatives 23. Heating of 23 in pivalic acid in the presence of a catalytic amount of trifluoroacetic acid
  • -monomethylation of the primary amino group of compound 25 by alkylation with methyl iodide or by Eschweiler–Clarke reductive amination with formaldehyde and formic acid were unsuccessful, because the dimethylated byproduct was also formed, even when one equivalent alkylating agent was used. Finally, our efforts
  • worth mentioning that in a similar reaction of 30 with NaCNBH3 in acetic acid (instead of TFA) we did not observe any reaction, however, with NaBH4 (instead of NaCNBH3) in TFA, the formation of 32 was detected. Conclusion In conclusion, a new method for the synthesis of β-carboline alkaloid brevicarine
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Published 20 May 2025

Harnessing tethered nitreniums for diastereoselective amino-sulfonoxylation of alkenes

  • Shyam Sathyamoorthi,
  • Appasaheb K. Nirpal,
  • Dnyaneshwar A. Gorve and
  • Steven P. Kelley

Beilstein J. Org. Chem. 2025, 21, 947–954, doi:10.3762/bjoc.21.78

Graphical Abstract
  • disulfonoxylation [2] and alkene amino-trifluoroacetoxylation [4], we hypothesized that treatment of (E)-hex-3-en-1-yl methoxycarbamate with a mixture of an I(III) oxidant and a sulfonic acid would lead to the formation of amino-sulfonoxylated product. We were thus very pleased to observe 59% of desired product B
  • using a combination of 1 equivalent of commercially available 1-acetoxy-1,2-benziodoxol-3-(1H)-one (CAS [1829-26-1]) and 1 equivalent of methanesulfonic acid (MsOH) (Table 1, entry 1). Increasing the equivalents of both reagents to 1.5 completely consumed starting material and delivered product B in an
  • other sulfonoxylated products, we found that stirring substrate with a combination of 1-acetoxy-1,2-benziodoxol-3-(1H)-one and the appropriate sulfonic acid worked best. Here, we hypothesize that rapid exchange of the acetate for the sulfonate occurred at the I(III) nucleus, and this unstable sulfonoxy
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Published 19 May 2025

A convergent synthetic approach to the tetracyclic core framework of khayanolide-type limonoids

  • Zhiyang Zhang,
  • Jialei Hu,
  • Hanfeng Ding,
  • Li Zhang and
  • Peirong Rao

Beilstein J. Org. Chem. 2025, 21, 926–934, doi:10.3762/bjoc.21.75

Graphical Abstract
  • Nazarov cyclization under a variety of conditions (Table 1). Initial trials under acid-mediated Nazarov conditions (AlCl3, BF3·Et2O and Me2AlCl) led to complete decomposition, while the exposure to AcOH resulted in recovery of the starting material (Table 1, entries 1–4). Recognizing the limitations of
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Published 12 May 2025

Silver(I) triflate-catalyzed post-Ugi synthesis of pyrazolodiazepines

  • Muhammad Hasan,
  • Anatoly A. Peshkov,
  • Syed Anis Ali Shah,
  • Andrey Belyaev,
  • Chang-Keun Lim,
  • Shunyi Wang and
  • Vsevolod A. Peshkov

Beilstein J. Org. Chem. 2025, 21, 915–925, doi:10.3762/bjoc.21.74

Graphical Abstract
  • [20][21][22][23]. For example, the Ugi four-component reaction (U4CR), involving a carbonyl compound, a primary amine, a carboxylic acid, and an isocyanide, provides a straightforward method for constructing dipeptide-like adducts [24][25][26][27]. These adducts can subsequently be rigidified into
  • involving the Ugi reaction between arylglyoxals 1, benzylamines 2, o-azidobenzoic acid (3), and cyclohexyl isocyanide (4a), followed by a triphenylphosphine-promoted tandem Staudinger/aza-Wittig cyclization (Scheme 1a) [33]. The overall strategy was enabled by the presence of an azide group in the
  • carboxylic acid component 3 and additional keto-carbonyl group in aryl glyoxal 1. This approach was further advanced by Ding's group to produce a broader range of benzodiazepines with diverse substitution patterns by shuffling the necessary functional groups within the Ugi reaction components [34][35][36
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Published 08 May 2025

Recent advances in controllable/divergent synthesis

  • Jilei Cao,
  • Leiyang Bai and
  • Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

Graphical Abstract
  • -29. This intermediate undergoes reductive elimination via an inner-sphere mechanism to generate the C(sp3)–N-coupled chiral product 22. Notably, benzoic acid acts as a critical additive, likely by stabilizing key intermediates and modulating the steric/electronic environment for enhanced
  • influence of steric and electronic effects during the hydrometallation process, simultaneously achieving the synthesis of chiral α-quaternary carbon amino acid derivatives 26 and α-chiral β-amino acid derivatives 27. Using a copper catalyst, the chiral α-quaternary carbon amino acid derivatives 26 were
  • obtained with exclusive regioselectivity and excellent enantioselectivity. Employing a nickel catalyst, α-chiral β-amino acid derivatives 27 were synthesized with single regioselectivity and outstanding enantioselectivity. In the same year, Rong and co-workers reported a highly efficient catalyst
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Published 07 May 2025

Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes

  • Patricia Gómez-Roibás,
  • Andrea Chaves-Pouso and
  • Martín Fañanás-Mastral

Beilstein J. Org. Chem. 2025, 21, 877–883, doi:10.3762/bjoc.21.71

Graphical Abstract
  • Patricia Gomez-Roibas Andrea Chaves-Pouso Martin Fananas-Mastral Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain 10.3762/bjoc.21.71 Abstract 4,4-Dichloro-2-butenoic acid derivatives
  • versatile building blocks for the stereoselective synthesis of chlorocyclopropanes. Keywords: chlorocyclopropanes; copper; cyclization; 4,4-dichloro-2-butenoic acid derivatives; dimerization; Introduction In the last years our group has been focused on the development of catalytic methodologies for the
  • mechanism for the copper-catalyzed diastereoselective dimerization of 4,4-dichoro-2-butenoic acid derivatives (Scheme 4). Initially, the LCu–pin complex generated through reaction between LCu–Ot-Bu and B2pin2 undergoes coordination and regioselective insertion into 1 giving rise to β-borylated organocopper
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Published 05 May 2025

Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters

  • Lewis McGhie,
  • Hannah M. Kortman,
  • Jenna Rumpf,
  • Peter H. Seeberger and
  • John J. Molloy

Beilstein J. Org. Chem. 2025, 21, 854–863, doi:10.3762/bjoc.21.69

Graphical Abstract
  • cyclobutyldiol. A) Product derivatization and B) transition-metal EnT catalysis. Reaction conditions A): 4d (1 equiv), H2O2 (30 wt % in H2O), aq NaH2PO4, THF, 0 °C; B) 4 (1 equiv), KF (4 equiv), ʟ-tartaric acid (2.1 equiv), MeOH, MeCN, H2O, rt. Probing EnT catalysis of alkenylboronic ester 1a via alkene
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Published 30 Apr 2025
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