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Search for "copper" in Full Text gives 762 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Copper catalysis: a constantly evolving field

  • Elena Fernández and
  • Jaesook Yun

Beilstein J. Org. Chem. 2025, 21, 1477–1479, doi:10.3762/bjoc.21.109

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  • Elena Fernandez Jaesook Yun Departament de Química Física i Inorgànica, University Rovira i Virgili, Tarragona, Spain Department of Chemistry, Sungkyunkwan University, Suwon 16419, Republic of Korea 10.3762/bjoc.21.109 Keywords: copper; copper catalysis; Copper catalysis continues to thrive as
  • one of the most dynamic and versatile areas of contemporary chemical research. Once viewed primarily as a cost-effective alternative to noble metals, copper has emerged as a powerful and versatile catalyst, capable of mediating a wide array of chemical transformations through both two-electron and
  • single-electron pathways. This duality has enabled access to previously elusive molecular transformations, positioning copper at the center of modern synthetic strategy. This thematic issue captures the dynamic nature of the field, featuring five insightful Review articles and five original research
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Published 17 Jul 2025

Microwave-enhanced additive-free C–H amination of benzoxazoles catalysed by supported copper

  • Andrei Paraschiv,
  • Valentina Maruzzo,
  • Filippo Pettazzi,
  • Stefano Magliocco,
  • Paolo Inaudi,
  • Daria Brambilla,
  • Gloria Berlier,
  • Giancarlo Cravotto and
  • Katia Martina

Beilstein J. Org. Chem. 2025, 21, 1462–1476, doi:10.3762/bjoc.21.108

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  • completed in 1.5–2 h. A solid Cu(I) catalyst supported on aminated silica made the process cost-effective and heterogeneous, thus simplifying work-up and minimising free copper in solution. The catalyst was found to be regeneratable and reusable for up to eight cycles. The optimised method facilitated the
  • synthesis of various benzoxazole derivatives, demonstrating its versatility and practical applicability. Keywords: aerobic oxidation; copper; grafted silica; heterogeneous catalysis; microwave; Introduction 2-Aminoazoles are nitrogenous heterocyclic compounds of high relevance due to their biological and
  • environmental abundance, low cost and low overall toxicity. A wide range of aminating reagents have been utilised, including nitrogen electrophiles and amines in the presence of external or internal oxidants [27], in many types of copper-catalysed synthetic protocols. The direct copper-catalysed C–H amination
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Published 15 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

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Published 27 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

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  • either a 1,5-hydride shift to give D or a direct cyclization with the aryl ring via intermediate E, which upon deprotonation lead to the final products 16 and 17. In a 2016 study by Van der Eycken’s group (Scheme 9), an innovative copper-catalyzed alkylarylation of activated alkenes using isocyanides as
  • -determining step. Based on these results, a detailed mechanism was proposed (Scheme 10) in which a copper-assisted homolysis of DCP generates a cumyloxyl radical A, which initiates the formation of an imidoyl radical B from the isocyanide. This radical then undergoes homolytic cleavage to yield an alkyl
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Published 24 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

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  • .21.96 Abstract Aerobic copper(II)-mediated phosphorylation of enol acetates with H-phosphonates leading to the formation of β-ketophosphonates was discovered. The proposed method is applicable to a wide range of H-phosphonates or phosphine oxides as PH-reagents and enol acetates. Unlike previous reports
  • , which generally employed stoichiometric amounts of oxidants or more expensive transition metal catalysts, the present protocol employs only cheap copper sulfate pentahydrate as a catalyst under mild reaction conditions. The achieved phosphorylation proceeds via the formation of P-centered radicals
  • produced by the oxidation of PH-reagents by copper(II)-containing species. Employing anhydrous CuSO4 instead of the pentahydrate led to a dramatic phosphorylation yield drop from 70 to <5%. It seems that the ligand environment of copper is very important for the effective reaction: other Cu(II) and Cu(I
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Published 20 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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  • the significant role of asymmetric catalysis in their strategy, utilizing a copper-catalyzed asymmetric 1,4-addition and a ruthenium-catalyzed asymmetric ketone hydrogenation. Fragment 61 was synthesized in 15% overall yield across 19 steps, while fragment 62b was achieved in 32% yield over 11 steps
  • . Herber and Breit’s strategy for constructing Theodorakis’ C3–C11 fragment In 2006, Herber and Breit utilized an iterative deoxypropionate synthesis to construct the Theodorakis’ C3–C11 fragment of borrelidin. This approach was based on a copper-mediated directed allylic substitution previously developed
  • ]. Synthesis of Ōmura’s C1–C11 fragment 61 by Minnaard and Madduri [37]. Synthesis of fragment 62b of borrelidin as proposed by Minnaard and Madduri [37]. Iterative directed allylation for the synthesis of deoxypropionates by Herber and Breit [33]. Iterative copper-mediated directed allyl substitution for the
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Published 12 Jun 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

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  • 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
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Published 28 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

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Published 21 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

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  • 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
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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

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  • 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
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Published 05 May 2025

Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones

  • Xuhong Zhao,
  • Weishuang Li,
  • Mengli Yang,
  • Bojie Li,
  • Yaoyao Zhang,
  • Lizhen Huang and
  • Lei Zhu

Beilstein J. Org. Chem. 2025, 21, 839–844, doi:10.3762/bjoc.21.67

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  • 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
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Published 28 Apr 2025

Regioselective formal hydrocyanation of allenes: synthesis of β,γ-unsaturated nitriles with α-all-carbon quaternary centers

  • Seeun Lim,
  • Teresa Kim and
  • Yunmi Lee

Beilstein J. Org. Chem. 2025, 21, 800–806, doi:10.3762/bjoc.21.63

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  • 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
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Published 17 Apr 2025

Recent advances in the electrochemical synthesis of organophosphorus compounds

  • Babak Kaboudin,
  • Milad Behroozi,
  • Sepideh Sadighi and
  • Fatemeh Asgharzadeh

Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61

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  • 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
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Published 16 Apr 2025

Copper-catalyzed domino cyclization of anilines and cyclobutanone oxime: a scalable and versatile route to spirotetrahydroquinoline derivatives

  • Qingqing Jiang,
  • Xinyi Lei,
  • Pan Gao and
  • Yu Yuan

Beilstein J. Org. Chem. 2025, 21, 749–754, doi:10.3762/bjoc.21.58

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  • 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
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Published 09 Apr 2025

Recent advances in allylation of chiral secondary alkylcopper species

  • Minjae Kim,
  • Gwanggyun Kim,
  • Doyoon Kim,
  • Jun Hee Lee and
  • Seung Hwan Cho

Beilstein J. Org. Chem. 2025, 21, 639–658, doi:10.3762/bjoc.21.51

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  • 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
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Published 20 Mar 2025

Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions

  • Xiao-Yang Bi,
  • Xiao-Shuai Yang,
  • Shan-Shan Chen,
  • Jia-Jun Sui,
  • Zhao-Nan Cai,
  • Yong-Ming Chuan and
  • Hong-Bo Qin

Beilstein J. Org. Chem. 2025, 21, 601–606, doi:10.3762/bjoc.21.47

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  • 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
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Published 17 Mar 2025

Sequential two-step, one-pot microwave-assisted Urech synthesis of 5-monosubstituted hydantoins from L-amino acids in water

  • Wei-Jin Chang,
  • Sook Yee Liew,
  • Thomas Kurz and
  • Siow-Ping Tan

Beilstein J. Org. Chem. 2025, 21, 596–600, doi:10.3762/bjoc.21.46

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  • 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
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Published 14 Mar 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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  • 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
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Published 13 Mar 2025

Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

  • Long K. San,
  • Sebastian Balser,
  • Brian J. Reeves,
  • Tyler T. Clikeman,
  • Yu-Sheng Chen,
  • Steven H. Strauss and
  • Olga V. Boltalina

Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39

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  • ): 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
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Published 07 Mar 2025

Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction

  • Thomas Brandt,
  • Pascal Lentes,
  • Jeremy Rudtke,
  • Michael Hösgen,
  • Christian Näther and
  • Rainer Herges

Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36

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  • 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
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Published 04 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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  • 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
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Published 03 Mar 2025

Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages

  • Keith G. Andrews

Beilstein J. Org. Chem. 2025, 21, 421–443, doi:10.3762/bjoc.21.30

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  • ][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
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Published 24 Feb 2025

Red light excitation: illuminating photocatalysis in a new spectrum

  • Lucas Fortier,
  • Corentin Lefebvre and
  • Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

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  • [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
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Published 07 Feb 2025

Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions

  • Dmitry E. Shybanov,
  • Maxim E. Kukushkin,
  • Eugene V. Babaev,
  • Nikolai V. Zyk and
  • Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 262–269, doi:10.3762/bjoc.21.18

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  • 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
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Published 04 Feb 2025

Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization

  • Asahi Kanno,
  • Ryo Tanifuji,
  • Satoshi Yoshida,
  • Sota Sato,
  • Saori Maki-Yonekura,
  • Kiyofumi Takaba,
  • Jungmin Kang,
  • Kensuke Tono,
  • Koji Yonekura and
  • Hiroki Oguri

Beilstein J. Org. Chem. 2025, 21, 226–233, doi:10.3762/bjoc.21.14

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  • 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
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Published 28 Jan 2025
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