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Search for "copper" in Full Text gives 756 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Recent advances in synthetic approaches for bioactive cinnamic acid derivatives
Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85
- affording cinnamamide (99) in excellent yield. The reaction proceeds via the decarboxylated amide–copper complex 359 (Scheme 79B) [134] and could be scaled-up to a gram scale reaction. Cinnamic acid derivatives could also be accessed via multicomponent reactions. For example, Jana and Ghosh (2019) utilized
On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals
Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80
Recent advances in controllable/divergent synthesis
Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73
- hydrogen atom transfer (HAT)/chiral copper dual catalytic system that achieved regiodivergent and enantioselective C(sp3)–C(sp3) and C(sp3)–N oxidative cross-couplings between N-arylglycine ester/amide derivatives and abundant hydrocarbon C(sp3)–H feedstocks (Scheme 6) [24]. This methodology also
- represents a highly challenging direct C(sp3)–H asymmetric amination. Mechanistic insights: When using a bulky, electron-rich chiral bisphosphine ligand L6, the glycine ester substrate coordinates with the copper catalyst to form a key intermediate complex Int-26. The sterically hindered and electron-rich
- environment around the copper center disfavors a direct interaction with nucleophilic alkyl radicals. Instead, the reaction proceeds via an outer-sphere mechanism, where the alkyl radical reacts with the copper-activated C=N unsaturated bond, enabling stereocontrolled C(sp3)–C(sp3) coupling. In contrast, with
Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes
Beilstein J. Org. Chem. 2025, 21, 877–883, doi:10.3762/bjoc.21.71
- are shown to undergo a rare dimerization process when reacted with bis(pinacolato)diboron under copper catalysis. The reaction provides densely functionalized products with excellent levels of chemo-, regio-, and diastereoselectivity. This high degree of functionalization makes these products
- 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
- carboboration of unsaturated hydrocarbons [1][2][3][4][5][6][7]. In the course of our investigation of the copper-catalyzed borylative coupling of alkynes with allylic gem-dichlorides [3], we observed that alkyl 4,4-dichloro-2-butenoates deviated from the general reactivity trend. While allylic gem-dichlorides
Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones
Beilstein J. Org. Chem. 2025, 21, 839–844, doi:10.3762/bjoc.21.67
- methods, the cascade reaction between ortho-halogen (e.g., chlorine, bromine or iodine) substituted benzoic acids and amidines has become a prominent route to synthesize the corresponding quinazolinones [10][11][12][13][14][15][16][17][18]. In 2009, Fu and co-workers found that copper(I) could effectively
- promote this cascade reaction for the synthesis of quinazolinones without the need for additional ligands or additives (Scheme 1a) [7][10]. Since then, various copper-based catalysts, both homogeneous and heterogeneous, have been explored (Scheme 1b) [11][12][13][14][15][16]. For example, Wang’s group
- developed a magnetically recoverable and reusable Fe3O4 nanoparticle-supported copper(I) catalyst with excellent catalytic efficiency for quinazolinone synthesis [11]. In addition, Cai et al. reported that MCM-41-immobilized tridentate nitrogen-supported copper(I) [MCM-41-3N–CuI] served as a highly
Regioselective formal hydrocyanation of allenes: synthesis of β,γ-unsaturated nitriles with α-all-carbon quaternary centers
Beilstein J. Org. Chem. 2025, 21, 800–806, doi:10.3762/bjoc.21.63
- Seeun Lim Teresa Kim Yunmi Lee Department of Chemistry, Kwangwoon University, Seoul 01897, Republic of Korea 10.3762/bjoc.21.63 Abstract This study introduces a highly selective hydrocyanation method based on copper-catalyzed hydroalumination of allenes with diisobutylaluminum hydride, followed
- allenes, the development of hydrocyanation methodologies with a broadened substrate scope and improved regio- and stereoselectivity is of significant interest. Inspired by our study on the construction of all-carbon quaternary centers via functionalized allylaluminum reagents obtained from the copper
- centers [30][31][32][33]. Herein, we report a mild and efficient method for the regio- and (E)-stereoselective formal hydrocyanation of di- and trisubstituted allenes. Using DIBAL-H as the hydride source and TsCN as a readily available and bench-stable cyanating agent in the presence of a copper catalyst
Recent advances in the electrochemical synthesis of organophosphorus compounds
Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61
- electrochemical method. They have synthesized 30 different thiazole phosphine oxides with up to 91% yield at room temperature without using an external metal or oxidant. The reaction was carried out in an undivided cell using glassy carbon as the anode and foamed copper as the cathode electrodes at a constant
- and copper foam (CF) as a cathode at a constant current of 14 mA. Experiments confirmed that the trace amount of copper dissolved from the cathode had no catalytic effect on the reaction. The reaction proceeded via anodic oxidation of diphenylphosphine followed by a reaction with alkenes to give
- anode and cathode electrodes were graphite felt (GF) and platinum, respectively, at a constant current of 7 mA. When a platinum plate or a carbon rod was used instead of GF for the anode, and a nickel plate or copper plate was used for the cathode, the efficiency of the reaction decreased (Table 6
Copper-catalyzed domino cyclization of anilines and cyclobutanone oxime: a scalable and versatile route to spirotetrahydroquinoline derivatives
Beilstein J. Org. Chem. 2025, 21, 749–754, doi:10.3762/bjoc.21.58
- report the copper-catalyzed synthesis of tetrahydroquinoline derivatives via a domino reaction of aniline with cyclobutanone oxime. This method demonstrates a selective approach for generating bioactive tetrahydroquinoline scaffolds, which have broad applications in pharmaceutical chemistry. The reaction
- the desired product. Keywords: copper catalysis; cyclobutane-fused tetrahydroquinolines; domino cyclization reaction; green synthesis; Introduction Tetrahydroquinolines (THQs) represent a privileged scaffold in medicinal chemistry, exhibiting a broad spectrum of biological activities and serving as
- cyclobutanone oxime using a copper-catalyzed reaction under ambient air conditions (Scheme 1c). Results and Discussion With these considerations in mind, we explored the feasibility of synthesizing cyclobutane-fused spirotetrahydroquinolines (STHQs) through the reaction of arylamines with cyclobutanone oxime
Recent advances in allylation of chiral secondary alkylcopper species
Beilstein J. Org. Chem. 2025, 21, 639–658, doi:10.3762/bjoc.21.51
- attention due to their unique properties in stereoselective allylic substitution. This review highlights recent advances in copper-catalyzed asymmetric allylic substitution reactions with chiral secondary alkylcopper species, encompassing several key strategies for their generation: stereospecific
- transmetalation of organolithium and organoboron compounds, copper hydride catalysis, and enantiotopic-group-selective transformations of 1,1-diborylalkanes. Detailed mechanistic insights into stereochemical control and current challenges in this field are also discussed. Keywords: allylic substitution; chiral
- secondary organocopper; copper-mediated reaction; stereoselectivity; Introduction The transition-metal-catalyzed regio- and enantioselective allylic substitution represents a pivotal methodology in organic synthesis, providing remarkable versatility for complex molecule construction [1][2][3][4]. The
Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions
Beilstein J. Org. Chem. 2025, 21, 601–606, doi:10.3762/bjoc.21.47
- alcohol 19 was isolated in 89% yield. The copper-catalyzed replacement of the bromine substituent in 19 with a hydroxy group was achieved in the presence of a catalytic amount of oxalamide ligand I [13]. This transformation is critical for enabling further functionalization and the reaction conditions
Sequential two-step, one-pot microwave-assisted Urech synthesis of 5-monosubstituted hydantoins from L-amino acids in water
Beilstein J. Org. Chem. 2025, 21, 596–600, doi:10.3762/bjoc.21.46
- copper(I)-catalyzed reactions (48–71%) [13] and the four-component Ugi reaction [14] yields 48–71% and 27–67%, respectively. In addition, pyroglutamates with isocyanates, which provide exceptionally high yields (97–99%) [15], and dipeptides have been utilized in triflate-activated Mumm’s rearrangement
Formaldehyde surrogates in multicomponent reactions
Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45
- substituted styrene under copper(I) catalysis to give the target compounds via a Povarov reaction. A further aromatization process yields product I (Scheme 8, path I). In a closely related approach, the same group reported on the synthesis of quinolines from anilines and alkynes [37]. In this case, the alkyne
- derivatives are isolated as side-products. Interestingly, when Liu et al. [40] modified this reaction by using a copper(II) catalyst under aerobic oxidative conditions, the regioisomers III (2-arylquinolines) were obtained (Scheme 9). To rationalize this singular result, the authors proposed a mechanism in
- was carried out via copper catalysis or iodine–acid catalysis. Interestingly, when aliphatic amines are employed (R3 = n-Pr, n-Bu, product 8) only the N atoms are incorporated in the structure of the final product, probably because the high temperature favors the elimination of the alkyl group. The
Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene
Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39
- ): CF2C6F5I (19 µL, 0.11 mmol) was syringed into a glass ampoule containing anthracene (10 mg, 0.056 mmol) and copper powder (11 mg, 0.17 mmol) dissolved in DMSO, and degassed by a freeze-pump-thaw technique (3 × 10 min). The ampoule was then heated in an oil bath at 160 °C for 24 h. The reaction contents
- -10-bis(perfluorobenzyl)anthracene were mounted in a paratone oil on glass fiber rods glued to a small copper wire. X-ray diffraction data were collected at ChemMatCARS (CARS = consortium for advanced radiation sources) sector 15-B at the Advanced Photon Source (Argonne National Laboratory). The data
Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction
Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36
- provided the corresponding amino-substituted N-acetyl diazocine 21 (Scheme 1). Another option for carbon–heteroatom bond formation reactions are copper-catalyzed Ullmann-type reactions, which have already been applied to the parent diazocine [36][37]. The attempted synthesis of azide-functionalized N
Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions
Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33
- shield above each jar holder allows for irradiation of the reaction glass vessels from above using powerful LED lamps. First, photomechanochemistry facilitated the copper-photocatalyzed ATRA of sulfonyl chlorides and styrenes under fully aerobic conditions (Scheme 11A), a feature unattainable in
Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages
Beilstein J. Org. Chem. 2025, 21, 421–443, doi:10.3762/bjoc.21.30
- ][344][345], which show early promise for low-symmetry cavities with catalytic potential [42][43][44][340]. Notably, Otte has used semi-stepwise self-assembly via imine formation/reduction to access a robust organic cage with reduced-symmetry and internal functionality able to chelate a copper(I) ion
Red light excitation: illuminating photocatalysis in a new spectrum
Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22
- [Os(tpy)2]2+/red-light irradiation system well-suited for large-scale manufacturing. In this way, the authors have also tested different osmium complexes in various well-established photocatalyzed reactions such as copper, palladium, cobalt, and nickel metallophotoredox couplings using red light
- . While transition metals such as copper, palladium, cobalt, and nickel are well-established in catalyzed cross-coupling reactions, J. Cornella et al. have highlighted the reactivity of main-group elements like bismuth, which can mimic transition-metal behavior through oxidative addition. In their recent
- thulium nanoparticles [26] and the use of a molybdenum-centered [27] and tungsten-centered complexes have been described in the literature [28]. The work by O. S. Wenger et al. introduces a system that mimics the Z-scheme of photosynthesis, utilizing a copper(I) bis(α-diimine) complex in combination with
Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions
Beilstein J. Org. Chem. 2025, 21, 262–269, doi:10.3762/bjoc.21.18
- formaldehyde (generated from paraformaldehyde upon heating), an adduct of a methylidene derivative of a CH acid dienophile was detected in some cases only in reference [15] (when carrying out the reaction in a sealed tube in the presence of copper(II) acetate). However, in most reactions only the hetero-Diels
Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization
Beilstein J. Org. Chem. 2025, 21, 226–233, doi:10.3762/bjoc.21.14
- Japan Synchrotron Radiation Research Institute, 1-1-1 Kouto, Sayo, Hyogo, 679-5198, Japan Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan 10.3762/bjoc.21.14 Abstract The integration of copper(I)-catalyzed three-component
- involvement of a fluorescent intermediate in the cascade synthetic process. Keywords: cascade reactions; copper-catalyzed three-component coupling; gold-mediated 6-endo hydroamination; tandem cyclizations; tetrahydroisoquinoline alkaloids; Introduction The bis-tetrahydroisoquinoline (THIQ) alkaloid family
- modular synthetic strategy involving the cascading assembly of the left THIQ segment. A concise modular synthetic process was developed to construct the substructure 14 of saframycin A (1), featuring copper(I)-catalyzed three-component coupling, and subsequent tandem 2,3-diaminobenzofuran formation
Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations
Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12
- widely used as N-acylamide sources in amidation processes of challenging substrates, typically employing precious transition metals. However, these catalytic systems often present several challenges associated with cost, toxicity, stability, and recyclability. Among the 3d transition metals, copper
- advancements in the synthetic transformations of dioxazolones, with particular examples of copper salts. Keywords: amidation; copper salts; dioxazolones; electrophilic nitrogen; N-acyl nitrene; Introduction Dioxazolones, first synthesized and reported by Beck and co-workers [1], have been employed as
- iridium (Scheme 1b) [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. Notably, dioxazolones have primarily been studied in directed carbon–hydrogen amidation processes, which can circumvent the need for tedious prefunctionalizations. Copper catalysts have gained recognition and attracted
Recent advances in electrochemical copper catalysis for modern organic synthesis
Beilstein J. Org. Chem. 2025, 21, 155–178, doi:10.3762/bjoc.21.9
- electrochemistry and copper catalysis for various organic transformations. Keywords: copper; electrochemistry; radical chemistry; single-electron transfer; sustainable catalysis; Introduction Transition-metal-catalyzed cross-coupling has emerged as an effective method for forming carbon–carbon (C–C) and carbon
- –heteroatom (C–X, where X = N, O, or halogens) bonds in organic synthesis. Copper was one of the first transition metals employed in cross-coupling to form C–C and C–X bonds [1][2]. In 1901, Ullmann reported the first cross-coupling reaction for the formation of biaryl compounds in the presence of
- stoichiometric quantities of a copper reagent [3]. This pioneering work, known as the “classical Ullmann reaction”, was extended by Ullmann and Goldberg to enable the C–N and C–O bond formation [4][5][6]. Subsequently, key developments in Cu-catalyzed cross-coupling reactions were achieved, including the
Nickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C–F bond activation
Beilstein J. Org. Chem. 2025, 21, 146–154, doi:10.3762/bjoc.21.8
- (GlassContour) equipped with columns of activated alumina and supported-copper catalyst (Q-5) before use. 1,4-Dioxane and methanol were distilled from sodium, and stored over 4 Å molecular sieves. Unless otherwise noted, materials were obtained from commercial sources and used directly without further
Cu(OTf)2-catalyzed multicomponent reactions
Beilstein J. Org. Chem. 2025, 21, 122–145, doi:10.3762/bjoc.21.7
- Venezian 21, 20133, Milano, Italy 10.3762/bjoc.21.7 Abstract This review reports the achievements in copper(II) triflate-catalyzed processes concerning the multicomponent reactions, applied to the synthesis of acyclic and cyclic compounds. In particular, for the heteropolycyclic systems mechanistic
- insights were outlined as well as cycloaddition and aza-Diels–Alder reactions were included. These strategies have gained attention due to their highly atom- and step-economy, one-step multi-bond forming, mild reaction conditions, low cost and easy handling. Keywords: cascade process; copper catalysis
- ; heteropolycycles; multicomponent reactions; one-pot reaction; Introduction Copper has gained a relevant role in organic synthesis as an alternative to precious metals due to its low toxicity, ease of handling, high catalytic activity, and cost-effectiveness [1][2]. In recent years, Cu(OTf)2 has significantly
Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride
Beilstein J. Org. Chem. 2025, 21, 39–46, doi:10.3762/bjoc.21.4
- ][18][19][20][21][22][28][29], the presence of the copper salt results in overcoming this issue and leads to isolated yields above 90% (7–9) (Scheme 2). Therefore, the NaBH4/CuCl2 system was proved to work on aromatic ester, nitro, and α,β-unsaturated nitroalkene functionalities. Our work demonstrates
- role of the CuCl2 salt is pivotal to the success of this method. Studies on the reduction of CuCl2 by NaBH4 suggest that copper(II) is promptly reduced to free Cu(0), composing up to 96% of the products. The remaining 4% consist of Cu2O and negligible amounts of other copper species [32][33
- ]. Consistently, once the chloride is added, the reduction to free Cu(0) is visually indicated by the immediate disappearance of the blue color of the copper(II) solution, and the formation of a fine suspended black powder. The latter, as metallic copper particles, acts as the actual catalyst. Time plays a
Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives
Beilstein J. Org. Chem. 2024, 20, 3299–3305, doi:10.3762/bjoc.20.274
- was achieved in 5 steps starting from commercially available 2-bromo-4-fluoro-1-nitrobenzene (1, Scheme 1 and Scheme 2). For the preparation of the key intermediate 5 (Scheme 1), self-coupling of 1 in the presence of copper followed by reduction of the nitro group generated diamine compound 3 (89
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