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Search for "coupling" in Full Text gives 1947 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene
Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39
- -step reactions with anthraquinone starting materials [24], or by Ullman coupling reactions of acene bromides with perfluoroalkyl iodides [25]. Notably, direct UV photoinduced reactions between anthracene and perfluoroalkyl iodides in the presence of a reducing agent, Na2S2O3, yielded perfluoroalkylated
- and C6F5 moieties appeared in the expected regions of −δ = 71–74 ppm and −δ = 140–165 ppm, respectively. Through-space F–F coupling was observed between the CF2 group and the ortho-F atoms, resulting in a triplet and a multiplet, respectively. Using 1,4-C6H4(CF3)2 as an internal standard, the F/H mole
- the long ANTH axis (Figure S5 in Supporting Information File 1). This insulation further inhibits any electronic coupling between the columns. Having effectively zero π–π overlap should result in reduced electronic coupling between molecules, which may be a beneficial factor for OLED applications
Synthesis of the aggregation pheromone of Tribolium castaneum
Beilstein J. Org. Chem. 2025, 21, 510–514, doi:10.3762/bjoc.21.38
- is a destructive stored product pest. The aggregation pheromone of this pest was prepared via a new and effective strategy. The key steps include the ring-opening reaction of chiral 2-methyloxirane, the stereospecific inversion of chiral secondary tosylate, Li2CuCl4-catalyzed coupling of tosylate
- coupling, and finally leads to the target pheromones by olefin oxidation with RuCl3/NaIO4. Results and Discussion The retrosynthetic analysis of the aggregation pheromone (4R,8R)-1 is shown in Scheme 1. Obviously, the target pheromone (4R,8R)-1 could be synthesized via an oxidation of chiral terminal
- olefine (5R,9R)-12, which could be obtained through Li2CuCl4-catalyzed coupling of chiral tosylate (S)-10 with a Grignard reagent derived from (R)-1-bromo-2-methylbutane ((R)-11). The key chiral building block (S)-10 was envisaged to be prepared through a sequence of hydrolyzation, decarboxylation, borane
Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction
Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36
- switching efficiency in aqueous solutions. In order to investigate the chemistry of this promising photoswitch and to unlock further applications, we now investigate strategies for the synthesis of derivatives, which are based on cross-coupling reactions. Fourteen vinyl-, aryl-, cyano-, and amino
- -substituted diazocines were prepared via Stille, Suzuki, and Buchwald–Hartwig reactions. X-ray structures are presented for derivatives 1, 2 and 7. Keywords: cross-coupling; diazocine; N-acetyl diazocine; photoisomerization; photoswitch; thermal relaxation; Introduction Diazocines are frequently used
- substitution. Substituents such as halogen atoms must be introduced into the N-acetyl diazocine structure during the synthesis of the building blocks. In the present work we start from mono- and dihalogenated N-acetyl diazocine 2–4 (Figure 2) and focus on the further derivatization via cross-coupling reactions
Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction
Beilstein J. Org. Chem. 2025, 21, 473–482, doi:10.3762/bjoc.21.34
- organometallic catalysis [15], enzymatic catalysis [16], aminocatalysis [17][18][19], and hydrogen-bonding catalysis [20][21][22]. The Michael addition reaction is a versatile synthetic methodology that allows the formation of new carbon–carbon and carbon–heteroatom bonds through the coupling of electron-poor
Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions
Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33
- . Also in this case, the addition of toluene was beneficial and excellent yield of the corresponding product (10.2) was observed in 30 h of reaction. As a comparison, the latter reaction required 48 h in solution. Intriguingly, 10.3 could in turn be synthesized via a mechanochemical Suzuki coupling
- benefits of the photomechanochemical approach in the field of synthesis [77]. Specifically, they developed photomechanochemical conditions for the atom-transfer-radical addition (ATRA) of sulfonyl chlorides to alkenes, pinacol coupling of carbonyl compounds, decarboxylative acylation, and photocatalyzed [2
- traditional solution-phase synthesis. In fact, in the latter case, almost complete recovery of the starting material was observed. Second, the authors found that the replacement of diisopropylethylamine (DIPEA) with Hantzsch ester in the role of sacrificial reductant for the pinacol coupling of benzaldehyde
New tandem Ugi/intramolecular Diels–Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives
Beilstein J. Org. Chem. 2025, 21, 444–450, doi:10.3762/bjoc.21.31
- products were identified via NMR as 4,4a,5,6,7,7a-hexahydro-3aH-furo[2,3-f]isoindoles. The structures of compounds 5 were confirmed by NMR spectroscopy data (for details and discussion see Supporting Information File 1). The NMR data for the obtained furoindole skeleton signals and spin-coupling constants
The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation
Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27
- glycosylation reaction between the two extremes of substitution reactions enables the synthetic chemists to manoeuvre and design the coupling reactions according to the regio- and stereochemical demand. In chemical glycosylation, the role of protecting groups in directing the attack of the incoming nucleophile
Synthesis, characterization, antimicrobial, cytotoxic and carbonic anhydrase inhibition activities of multifunctional pyrazolo-1,2-benzothiazine acetamides
Beilstein J. Org. Chem. 2025, 21, 348–357, doi:10.3762/bjoc.21.25
- complex as the amide coupling agent with thionyl chloride [38] (Figure 1C). Recently, benzothiazine scaffolds of phenyl acetamides were synthesized as potent inhibitors for ureolytic infections [39] (Figure 1D). Saccharine (a sweetener) was reported to be a potent carbonic anhydrase inhibitor (CAI) by
- pain [48], cancer [41], hypertension (as diuretics) [41], and arthritis [49]. This article introduces a new approach to synthesize the targeted scaffolds from commercially available saccharine without using amide coupling agents to minimize the cost. This work is the first attempt to put pyrazolo-1,2
- . Finally, none of the pyrazolobenzothiazine scaffolds showed hCA inhibition activity comparable to acetazolamide (AAZ, reference drug). Conclusion In summary, an economical multistep synthesis approach without using any coupling reagents for the synthesis of new multifunctional pyrazolo-1,2-benzothiazines
Red light excitation: illuminating photocatalysis in a new spectrum
Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22
- sustainable photocatalysis, with applications ranging from selective oxidation to cross-dehydrogenative coupling. These organic systems are valued for their reduced environmental impact, their wide availability, and tunability, making them viable alternatives to traditional metal-based catalysts for red-light
- + and 660 nm for [Os(phen)3]2+ [15]. In a same way, spin–orbit coupling, stemming from the relativistic effects, can be exploited in photoredox-catalyzed reaction [16]. Spin–orbit coupling promotes intersystem crossing (ISC) between the singlet and triplet excited states, and even allows for direct
- , thereupon highlighting potential for broad applications in photoredox catalysis on an industrial scale. In this context, T. Rovis et al. have studied a C–N cross-coupling Buchwald–Hartwig-like reaction using dual nickel and osmium catalysis under red-light activation, addressing common challenges such as
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
- alcohol 2. Its 1H NMR spectrum contained a triplet with a coupling constant of 5.1 Hz at 5.52 ppm and a doublet at 4.30 ppm. In methanol, ethanol and petroleum ether, with an increasing reaction time, a significant amount of product 3 was observed in the 1H NMR spectra of the mixtures, as identified by
Synthesis of disulfides and 3-sulfenylchromones from sodium sulfinates catalyzed by TBAI
Beilstein J. Org. Chem. 2025, 21, 253–261, doi:10.3762/bjoc.21.17
- antibody–drug coupling (ADCs), in which the active drug released in the target cell by selectively breaking the disulfide bond [11]. Given the wide applicability of disulfides, the development of efficient, green, mild, and cost-effective methods for the organic synthesis of disulfides is of significant
- reaction at 120 °C for 2 hours were determined as optimal conditions for the reaction (Table 1, entry 14). Under the optimized conditions, the coupling reaction of various sodium arylsulfinates was investigated to assess the scope and generality of this protocol. The results, shown in Scheme 2
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
- coupling with gold(I)-mediated 6-endo cyclization streamlines the rapid and modular assembly of the substructure of bis-tetrahydroisoquinoline (THIQ) alkaloids. The design of the key synthetic intermediate bearing a 2,3-diaminobenzofuran moiety allows both gold(I)-mediated regiocontrolled 6-endo
- 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
- condensation of carboxylic acids with anilines, often promoted by activating agents such as thionyl chloride or peptide coupling agents [86][87][88][89]. However, these protocols rely on environmentally harmful reagents and produce unwanted byproduct wastes. Recently, the research group of Son showcased a
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
- , Ibaraki 305-8571, Japan Sagami Chemical Research Institute, 2743-1 Hayakawa, Ayase, Kanagawa 252-1193, Japan 10.3762/bjoc.21.8 Abstract 2-Fluorobenzofurans underwent efficient nickel-catalyzed coupling with arylboronic acids through the activation of aromatic C–F bonds. This method allowed us to
- coupling reactions of aromatic C–F and C–Br bonds with arylboronic acids. Keywords: arylboronic acid; benzofuran; C–F bond activation; cross-coupling; nickel; Introduction The metal-catalyzed activation of aromatic carbon–fluorine (C–F) bonds is widely recognized as a challenging task in synthetic
- are generated by treating 1,1-difluoroethylenes with a zirconocene equivalent (ZrCp2, Scheme 1a) [8]. The resulting 1-fluorovinylzirconocenes B then undergo palladium-catalyzed coupling with aryl iodides to produce arylated fluoroethylenes. Additionally, (ii) we observed that electron-deficient 2
Cu(OTf)2-catalyzed multicomponent reactions
Beilstein J. Org. Chem. 2025, 21, 122–145, doi:10.3762/bjoc.21.7
- ]. Three-component coupling of amines, aldehydes or ketones, and terminal alkynes catalyzed by Cu(OTf)2 is a fruitful tool for the production of α-substituted propargylamines 10 (Scheme 7) [20]. The reaction involves the alkynylation of the corresponding imines formed in situ and provides higher yields
- alkyltrifluoroborate into its corresponding alkyl radical. o-Halo-substituted aryl selenides and sulfides 13 can be achieved by a three-component coupling reaction performed with an aryne precursor, potassium halides and electrophilic chalcogen species as reactants, in the presence of Cu(OTf)2 (Scheme 10) [23]. Under
- Pd-catalyzed cross-coupling reactions, allowing the formation of C–C and C–N bonds in the o-position of the aryl chalcogen compounds. α-Aminophosphonates 14 were the result of a one-pot condensation of an aldehyde, a primary amine and phosphite P(OMe)3 with copper triflate acting as Lewis acid
Recent advances in organocatalytic atroposelective reactions
Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6
- organocatalytic cross-coupling reaction of 1-azonaphthalenes 238 with 2-naphthols 239 catalyzed by chiral N-triflylphosphoramide C56 was done in 2023 (Scheme 70) [104]. A remarkable number of axially chiral products 240 were prepared with excellent enantiomeric purities and high yields. Undiminished yields and
Emerging trends in the optimization of organic synthesis through high-throughput tools and machine learning
Beilstein J. Org. Chem. 2025, 21, 10–38, doi:10.3762/bjoc.21.3
- selection, a dispensing module for solids and liquids, a reaction module capable of heating and stirring, a sample preparation module, and a LC–MS characterization module (Figure 2d). The efficiency of the system has been demonstrated in three reactions types, namely Suzuki–Miyaura coupling, Buchwald
- –Hartwig amination, and Ullmann coupling. These experiments showcased a conversion rate that outperformed existing reference systems and provided at least six times the efficiency in the experimentation, besides synthesis planning, optimization, and downstream workup tasks. The throughput of SynBot is
- were explored, using a total volume of 4.5 mL reaction mixture, and the screening results can be readily translated to continuous flow synthesis. The application of segmented flow or microslug reactors was demonstrated in the decarboxylative arylation cross-coupling reaction promoted by catalysts and
Synthesis, structure and π-expansion of tris(4,5-dehydro-2,3:6,7-dibenzotropone)
Beilstein J. Org. Chem. 2025, 21, 1–7, doi:10.3762/bjoc.21.1
- Abstract The polycyclic skeleton of tris(4,5-dehydro-2,3:6,7-dibenzotropone) is a key structural fragment in carbon schwarzites, a theoretical form of negatively curved carbon allotrope. This report presents a new synthesis of this compound using a Ni-mediated Yamamoto coupling reaction and structural
- , expanding its π-skeleton through the Barton–Kellogg and Scholl reactions led to the successful synthesis of a curved polycyclic arene containing three heptagons and two pentagons. Keywords: carbon schwarzites; polycyclic arenes; Scholl reaction; seven-membered carbocycle; Yamamoto coupling; Introduction
- synthesis of 1 using a Ni-mediated Yamamoto coupling reaction and the simultaneous crystallization of its two different conformers from the same solution. Expanding the π-skeleton of 1 through a Barton–Kellogg reaction followed by a subsequent Scholl reaction resulted in a new polycyclic arene (3 in Figure
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
Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade
Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273
- %). This cascade involves an initial Suzuki–Miyaura cross-coupling reaction between 1,8-dihalonaphthalenes and heteroarylboronic acids or esters, followed by an intramolecular C–H arylation under the same conditions to yield the final heterocyclic fluoranthene analogues. The method was further employed to
- )-catalyzed [2 + 2 + 2] cycloaddition reactions with 1,8-dialkynylnaphthalenes to access azafluoranthenes and 2-pyridone-fused naphthalenes [27]. In 2017, we reported a Pd-catalyzed cascade reaction that involves a sequential Suzuki–Miyaura cross-coupling and a subsequent intramolecular C–H arylation between
- boronic esters of 1,8-DHN have recently been investigated and reported by Krempner and co-workers [51]. To our delight, the Suzuki–Miyaura coupling/intramolecular C–H arylation sequence between 12 and boronic ester 17d proceeded smoothly affording product 15a in 84% yield. The results summarized in Table
Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases
Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270
- commercial perfluoroarene chemical blocks and reagents, involving catalyzed C–F-bond activation and cross-coupling reactions, usually requiring precious transition-metal catalysts and tedious synthetic routes [28][29][30][31][32][33][34]. Therefore, low-cost and facile synthetic strategies are desired to
- prepared in high yield via FeCl3-oxidative coupling of 1,2-dialkoxy-4-bromobenzene (Scholl reaction). The new triphenylene derivatives, F3–F12, were prepared in moderate to high yields (51–73%). In addition, three bitriphenylene derivatives were synthesized in a subsequent annulation step from Fn
- ) was synthesized via consecutive Suzuki coupling and Scholl reaction in a total yield of 77%. The synthesis, molecular structures, nomenclature, and synthetic yields of all compounds are shown in general Scheme 1. All prepared molecules were fully characterized by NMR (1H, 19F and 13C), HRMS, and CHN
Intramolecular C–H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds
Beilstein J. Org. Chem. 2024, 20, 3256–3262, doi:10.3762/bjoc.20.269
- conditions. We carried out the palladium-catalyzed intramolecular coupling reaction of precursor 1a under similar conditions [23], which afforded smooth reaction with phenanthroline bisamide, with 10 mol % of palladium acetate as a catalyst in the presence of potassium carbonate and tetra-n-butylammonium
Germanyl triazoles as a platform for CuAAC diversification and chemoselective orthogonal cross-coupling
Beilstein J. Org. Chem. 2024, 20, 3198–3204, doi:10.3762/bjoc.20.265
- further diversification of the triazole products, including chemoselective transition metal-catalysed cross-coupling reactions using bifunctional boryl/germyl species. Keywords: chemoselectivity; click chemistry; copper; germanium; triazole; Introduction Since its inception, click chemistry has been
- cross-couplings. Schoenebeck and co-workers have shown that Ge-based compounds are versatile reagents within chemoselective cross-coupling processes for the formation of a variety of C–C and C–X bonds [55][56][57][58][59][60][61][62][63]. Importantly, these transformations can take place in the presence
- of borylated functional groups, allowing orthogonal cross-coupling, whilst also offering excellent stability compared to boron-based reagents [57][58][59][60][61][62][63][64][65][66][67]. Based on their utility and stability, germanium units could therefore be useful within CuAAC reactions and offer
Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds
Beilstein J. Org. Chem. 2024, 20, 3182–3190, doi:10.3762/bjoc.20.263
- fluoroalkyliodonium salts as sources of electrophilic trifluoroethyl synthon. Given the non-nucleophilic nature of the iodoarene byproduct, this protocol should not suffer from further reactivity that decomposes the ylide. We describe here the coupling of α-carbonyl sulfoxonium ylides with polyfluoroalkyl(aryl
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