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Search for "catalytic" in Full Text gives 1672 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Asymmetric Mannich reaction of aromatic imines with malonates in the presence of multifunctional catalysts
Beilstein J. Org. Chem. 2026, 22, 151–157, doi:10.3762/bjoc.22.8
- ], halogen bonding is more frequently employed as a component of multifunctional catalytic systems [23][24][25]. Multifunctionality of the catalyst is essential to intensify weak noncovalent interactions. Results and Discussion As a continuation of our previous studies [18][24], we now report an asymmetric
- catalyst and the imine and malonate attacks from si-face affording the product in S-configuration (Figure 2). To demonstrate the utility of the elaborated catalytic system, the Mannich reaction between aromatic imines, both with electron-withdrawing and electron-donating substituents in the phenyl ring
- method and applications of obtained products are under study. Experimental General procedure for the catalytic asymmetric Mannich reaction Catalyst E (2.7 mg, 0.0057 mmol, 0.01 equiv) was weighed into a reaction vessel, imine (0.057 mmol, 1.0 equiv) and toluene (285 µL) were added. The mixture was
Total synthesis of natural products based on hydrogenation of aromatic rings
Beilstein J. Org. Chem. 2026, 22, 88–122, doi:10.3762/bjoc.22.4
- saturation the aromatic ring facilitates synthetic chemists to efficiently synthesize natural products with complex three-dimensional structures. Recent advances in catalyst and ligand design have enabled unprecedented progress in the catalytic hydrogenation of (hetero)aromatic systems. Quinoline
- , isoquinoline, pyridine, and related substrates can now be reduced with high efficiency and stereoselectivity, providing efficient access to saturated and partially saturated architectures vital to synthetic chemistry. Furthermore, catalytic asymmetric aromatic hydrogenation has facilitated the asymmetric total
- synthesis of complex natural products and pharmaceutical agents. This review highlights recent advances in catalytic (hetero)arene hydrogenation, with a focus on its application in natural product synthesis. Keywords: aromatic rings; dearomatization; hydrogenation; natural products; total synthesis
Advances in Zr-mediated radical transformations and applications to total synthesis
Beilstein J. Org. Chem. 2026, 22, 71–87, doi:10.3762/bjoc.22.3
- and accelerating the whole process. Zr-mediated catalytic radical reactions In recent years, numerous chemical transformations employing photoredox catalysts in combination with catalytic amounts of zirconium complexes have been reported. In this section, representative examples of such reactions are
- the strong affinity of zirconium for halogens, they developed a catalytic system to address this issue. Treatment of alkyl chloride 34 with zirconocene bistosylate in the presence of an Ir-photoredox catalyst promoted halogen atom transfer to generate alkyl radical 35. This radical then abstracted a
- yields. The catalytic system was further extended to the borylation of alkyl chlorides. (Scheme 7B). Under XAT conditions with B2(cat)2, the in situ-generated alkyl radical was trapped by diborane compound to form intermediate 39, which was subsequently converted into pinacol boronate 40 upon treatment
Synthesis and applications of alkenyl chlorides (vinyl chlorides): a review
Beilstein J. Org. Chem. 2026, 22, 1–63, doi:10.3762/bjoc.22.1
- stereocontrolled olefin metathesis with molybdenum catalysts to access trisubstituted alkenes including alkenyl chlorides (Figure 3H) [39]. Two recent reviews by Lu [40] and Nishiwaki [41] provide overviews of current developments in the hydrochlorination of alkynes, highlighting emerging catalytic strategies
- of the desired products (Scheme 20B). The authors proposed that BTC functions by regenerating benzoyl chloride in situ from benzoic acid, thereby allowing the use of benzoyl chloride in catalytic quantities (Scheme 20C). Under similar conditions – benzoyl chloride (2.2 equiv), room temperature
- ZnCl2·etherate exhibits superior catalytic activity compared to anhydrous ZnCl2. Although counterintuitive from the standpoint of Lewis acidity, this enhanced reactivity was attributed to the significantly improved solubility of the etherate complex, which compensates for its diminished intrinsic Lewis
Total synthesis of asperdinones B, C, D, E and terezine D
Beilstein J. Org. Chem. 2025, 21, 2730–2738, doi:10.3762/bjoc.21.210
- Discussion Adopting approach A, we considered prenylation of the known methyl (2S)-((tert-butoxycarbonyl)amino)-3-(7-iodo-1H-indol-3-yl)propanoate (7) [30] with prenylzinc bromide using a catalytic system reported by Buchwald. In that study, Buchwald’s group achieved the C-6 prenylation of 6-bromoindole in
Visible-light-driven NHC and organophotoredox dual catalysis for the synthesis of carbonyl compounds
Beilstein J. Org. Chem. 2025, 21, 2584–2603, doi:10.3762/bjoc.21.200
- carbonyl compounds and pharmaceutically relevant intermediates. Moreover, this catalytic system operates under green and sustainable conditions, tolerating a broad range of functional groups and substrate scope, and utilizes low-cost, atom-economical, non-toxic starting materials. Keywords: dual catalysis
- functional groups are found in various drugs, natural products, and optoelectronic materials. In the last three decades, N-heterocyclic carbenes (NHCs) have been renowned as versatile organocatalysts, including thiazolium, imidazolium, and triazolium moieties. NHCs are extensively used in many catalytic
- equivalents, which is crucial in dual or triple catalytic cycles. The electron-rich carbene center facilitates faster SET processes in photocatalytic reactions. Triazolium-based NHCs exhibit higher oxidative and photochemical stability, making them well-suited for visible-light-driven catalytic
Total syntheses of highly oxidative Ryania diterpenoids facilitated by innovations in synthetic strategies
Beilstein J. Org. Chem. 2025, 21, 2553–2570, doi:10.3762/bjoc.21.198
- atmosphere significantly suppressed side reactions, yielding the cyclized product in excellent yield and selectivity. This indicates that N-formylsaccharin, beyond acting as a CO-releasing agent, may function as a ligand in the catalytic cycle to regulate the palladium catalyst’s activity and stability
Pentacyclic aromatic heterocycles from Pd-catalyzed annulation of 1,5-diaryl-1,2,3-triazoles
Beilstein J. Org. Chem. 2025, 21, 2524–2534, doi:10.3762/bjoc.21.194
- modification of the base-catalyzed conditions reported by Kwok [53], where a stoichiometric plus additional catalytic amount of tetraethylammonium hydroxide base in DMSO solvent was used to promote tandem trimethylsilyl deprotection and cycloaddition in one preparation (Figure 3). Isolated yields of this
Palladium-catalyzed regioselective C1-selective nitration of carbazoles
Beilstein J. Org. Chem. 2025, 21, 2479–2488, doi:10.3762/bjoc.21.190
- catalytic pathway through a series of experiments (Scheme 5). To probe the nature of the C–H activation step, the reaction was conducted in fully deuterated methanol as both cosolvent and solvent (Scheme 5a). No H/D scrambling was observed at the C1 position of the recovered starting material 1a, suggesting
- palladacycle 6 as the catalyst, and the desired nitrated product 2a was obtained in 48% yield (Scheme 5c). This result supports the involvement of palladacycle intermediate 6 in the catalytic cycle. Proposed mechanism Based on our experimental results and related literature precedents [68][69][74][75][76][77
- ][78][79][80], a plausible catalytic cycle is proposed (Figure 2). The catalytic cycle commences with the formation of active palladium(II) species 7 in the presence of AgNO3. Coordination of the pyridyl group of 1a to Pd(NO₃)₂ is followed by irreversible C–H bond cleavage via cyclopalladation to form
Synthesis of the tetracyclic skeleton of Aspidosperma alkaloids via PET-initiated cationic radical-derived interrupted [2 + 2]/retro-Mannich reaction
Beilstein J. Org. Chem. 2025, 21, 2470–2478, doi:10.3762/bjoc.21.189
- undergo reductive SET in the presence of [FCNIr(II)Pic]−. This leads to the regeneration of [FCNIr(III)Pic] to complete the catalytic cycle and formation of the final product via proton transfer. Intrinsic reaction coordinate (IRC) analysis showed the reaction coordinate connecting the transition state
Ex-situ generation of gaseous nitriles in two-chamber glassware for facile haloacetimidate synthesis
Beilstein J. Org. Chem. 2025, 21, 2465–2469, doi:10.3762/bjoc.21.188
- trifluoroacetimidates to be more stable than their trichloroacetimidate counterparts [25]. Since these early examples trichloroacetimidates have become one of the most common glycosyl donors used in catalytic glycosylation, whereas the trifluoroacetimidates have received much less attention. Results and Discussion We
- used building blocks in glycosylations. For the synthesis chamber (A) was loaded with trifluoroacetamide (6 equiv) in pyridine. In the other chamber (B), the hemiacetal (ca. 500 mg, 1 equiv) was dissolved in CH2Cl2 together with a catalytic amount of DBU. Upon addition of trifluoroacetic anhydride
The intramolecular stabilizing effects of O-benzoyl substituents as a driving force of the acid-promoted pyranoside-into-furanoside rearrangement
Beilstein J. Org. Chem. 2025, 21, 2456–2464, doi:10.3762/bjoc.21.187
- observed another example of the PIF-rearrangement [31] where treatment with catalytic amounts of TfOH in CH2Cl2 unexpectedly shifted the equilibrium between selectively protected galactoside 1 and furanoside 2 in favor of the furanose form (Figure 3A), thus opening a new route towards Galf-containing
Catalytic enantioselective synthesis of selenium-containing atropisomers via C–Se bond formations
Beilstein J. Org. Chem. 2025, 21, 2447–2455, doi:10.3762/bjoc.21.186
- Atropisomers are not only prevalent in biologically active natural products and pharmaceuticals, but they have also garnered increasing attention for their effectiveness as ligands and catalysts in the field of catalytic asymmetric synthesis. Asymmetric catalysis serves as a key strategy for the
- currently lacking. This review aims to provide an overview of recent developments in the catalytic enantioselective synthesis of selenium-containing atropisomers via C–Se bond formation. We hope this review will serve as a valuable reference for researchers interested in further exploring this area
- participate in various types of asymmetric reactions, significantly improving the selectivity of reactions (Figure 1) [10][11][12][13][14]. Catalytic asymmetric synthesis is the main method to construct chiral organic selenium-containing compounds. Centrally chiral selenium-containing compounds can be
Transformation of the cyclohexane ring to the cyclopentane fragment of biologically active compounds
Beilstein J. Org. Chem. 2025, 21, 2416–2446, doi:10.3762/bjoc.21.185
- 111 led to (±)-preterrenoid (107) with 68% yield, which was subjected to stereoselective oxidation with magnesium monoperoxyphthalate (MMPP) to give (±)-terrenoid (108) as a single diastereomer. Subsequent treatment of the key precursor 108 with catalytic amounts of NaOMe in MeOH resulted in
- of reactivity, they are environmentally sustainable alternatives to heavy metals. The advantage of hypervalent catalytic systems based on iodine lies in their reusability [63]. The oxidative contraction of the tetralone cycle 117 depended on the stoichiometric amounts of iodine(III)-based chiral
The high potential of methyl laurate as a recyclable competitor to conventional toxic solvents in [3 + 2] cycloaddition reactions
Beilstein J. Org. Chem. 2025, 21, 2389–2415, doi:10.3762/bjoc.21.184
- is fully consumed by the end of the five-minute reaction period. In academic and industrial communities alike, there is a high level of interest in catalytic methods of Green Chemistry that allow stereoselective transformations [125][126][127][128]. It is imperative to develop stereoselective
- synthetic methods for cycloaddition reactions. In this study, a series of natural organic compounds from diverse classes and an acetonide [129] derivative were selected for investigation, with a focus on their potential catalytic effects in relation to the alteration of cis/trans product distribution under
An Fe(II)-catalyzed synthesis of spiro[indoline-3,2'-pyrrolidine] derivatives
Beilstein J. Org. Chem. 2025, 21, 2383–2388, doi:10.3762/bjoc.21.183
- cyclization. Subsequently Zhong et al. reported a catalytic asymmetric variant, affording spirooxindoles in high yields with excellent enantioselectivity [8]. An alternative approach employing vinyl azides involves a Rh(II)-catalyzed olefination of diazo compounds, followed by annulation with vinyl azides to
Rotaxanes with integrated photoswitches: design principles, functional behavior, and emerging applications
Beilstein J. Org. Chem. 2025, 21, 2345–2366, doi:10.3762/bjoc.21.179
- chromophores via photoinduced electron and energy transfer within the pyrene–perylene dyad. This interlocked system functions as a fluorescence switch, presenting strong potential for optical applications. Martínez-Cuezva and co-workers synthesized photoswitchable [2]rotaxanes for catalytic applications. They
- incorporated a photoswitchable fumaramide and a thiodiglycolamide unit as recognition sites along the axle of the interlocked system [68]. The catalytic performance of the [2]rotaxane was assessed in a TiCl4-promoted Baylis–Hillman reaction between p-nitrobenzaldehyde and 3-butyn-2-one, where the trans
Recent advances in Norrish–Yang cyclization and dicarbonyl photoredox reactions for natural product synthesis
Beilstein J. Org. Chem. 2025, 21, 2315–2333, doi:10.3762/bjoc.21.177
- under catalytic conditions – may lead to novel strategies for C–H functionalization and fragment coupling, ultimately advancing the field of target-oriented synthesis. Combining Norrish–Yang reaction with flow chemistry technology to realize the continuous operation of the reaction can improve the
Enantioselective radical chemistry: a bright future ahead
Beilstein J. Org. Chem. 2025, 21, 2283–2296, doi:10.3762/bjoc.21.174
- describes several important catalytic asymmetric strategies applied to enantioselective radical reactions, including chiral Lewis acid catalysis, organocatalysis, photoredox catalysis, chiral transition-metal catalysis and photoenzymatic catalysis. The application of electrochemistry to asymmetric radical
- enantioenriched catalysts ranging from chiral organometallic complexes to organocatalysts (small organic molecules) have been designed, synthesized, and successfully used in several organic transformations [1][2][3]. Despite these advances, catalytic methods involving radical intermediates were very rare until
- , initial examples of catalytic methodologies were based on chiral Lewis acid catalysis, with catalysts used in stoichiometric or sub-stoichiometric amounts [38][39]. Porter and Sibi disclosed the first enantioselective examples of conjugate additions to electron-deficient olefins by nucleophilic radicals
Pathway economy in cyclization of 1,n-enynes
Beilstein J. Org. Chem. 2025, 21, 2260–2282, doi:10.3762/bjoc.21.173
- ligands could enhance catalytic activity and efficiency while enabling fine control over chemo-, regio-, stereo-, and enantioselectivity of reactions. Ligands enhance both the thermal/chemical stability and solubility profiles of catalysts in specific reaction media. Thus, ligands function as a regulatory
- nexus for the rational design and optimization of highly effective, selective homogeneous catalytic systems. In 2013, Barriault and co-workers demonstrated that strategic modulation of steric and electronic ligand parameters within gold(I)-catalyzed cyclization pathways enables the selective assembly of
- /cycloisomerization sequences. In 2019 and 2020, Liu and co-workers achieved pathway-controlled cyclization–isomerization of tryptamine-ynamides using ligand-influenced silver catalytic systems (Scheme 19) [27][28][29]. To circumvent decomposition caused by the inherent high reactivity of ynamides under catalytic
Pd-catalyzed dehydrogenative arylation of arylhydrazines to access non-symmetric azobenzenes, including tetra-ortho derivatives
Beilstein J. Org. Chem. 2025, 21, 2234–2242, doi:10.3762/bjoc.21.170
- (OAc)₂/BINAP catalytic system [51], which enabled selective C–N coupling at the terminal nitrogen and suppressed denitrogenative by-products [52][53][54]. Although the general strategy is similar, our method uses the [PdCl(C3H5)]2/t-BuXPhos catalytic system, which provided higher yields and broader
- proposed. In the first step a C–N-coupling reaction with phenylhydrazine occurs [57]. The catalytic cycle starts by the formation of Pd(0) in situ through reduction facilitated by phosphine and water [58]. This is followed by the oxidative addition of aryl bromides, leading to the formation of the Pd(II
- formed to minimize steric clashes. Finally, reductive elimination leads to the formation of N,N-diarylhydrazine (D), which has been identified and characterized during the optimization process (see Supporting Information File 1 for details). In a second catalytic cycle, the N,N-diarylhydrazine (D
C2 to C6 biobased carbonyl platforms for fine chemistry
Beilstein J. Org. Chem. 2025, 21, 2103–2172, doi:10.3762/bjoc.21.165
- chemistry [3][4][5][6]. Indeed, the use of biobased feedstocks provide a promising substitute for traditional petroleum-based resources [7]. Particularly lignocellulosic materials have emerged as a key source of producing fine chemicals and fuels [8][9], relying on the advances in catalytic processes
- acetal as source of glycolaldehyde, two catalytic systems, namely Sc(OTf)3/nitromethane and Ni(ClO4)2·6H2O/acetonitrile, resulted in good yields. When using directly the aqueous solution of glycolaldehyde, these latter conditions were unproductive, whereas the deep eutectic solvent (DES) system FeCl3
- hydroxy group at the α-position of the carboxyl group (Scheme 10) [38]. Yang and his team reported a metal-free catalytic system for the conversion of LA to PA (Scheme 10a). The use of NaI as catalyst and PA itself as solvent allowed to simplify the product separation process, giving yields up to 99
The application of desymmetric enantioselective reduction of cyclic 1,3-dicarbonyl compounds in the total synthesis of terpenoid and alkaloid natural products
Beilstein J. Org. Chem. 2025, 21, 2085–2102, doi:10.3762/bjoc.21.164
- cyclic prochiral dicarbonyl substrates. In addition, various approaches could be used for the desymmetrization reactions such as enzyme catalytic-, organocatalyst-, and transition-metal-catalyzed reductions [5][6][7]. Advance about the synthesis of several terpenoid and alkaloid natural products (1–5
- group [35][36][37]. This catalytic system efficiently overcame the challenge and furnished the coupling product 46 in high yield. Oxidative cleavage of the double bond in 46 followed by Mg(II)-mediated chelation-controlled Friedel–Crafts cyclization delivered secondary alcohol 47, which was elaborated
- the unprecedented spiroannulated 6/6/6/5/5/3 (A/B/C/D/E/F) hexacarbocyclic motif and exhibit significant antifeedant activity against the pest insect Spodoptera litura [85]. In a very recent report, Han and co-workers accomplished the first catalytic asymmetric total syntheses of 26 and 27 via a
Further elaboration of the stereodivergent approach to chaetominine-type alkaloids: synthesis of the reported structures of aspera chaetominines A and B and revised structure of aspera chaetominine B
Beilstein J. Org. Chem. 2025, 21, 2072–2081, doi:10.3762/bjoc.21.162
- (13) for aspera chaetominine B. To our delight, one-pot catalytic debenzylation–lactamization of 29 afforded lactamization product (–)-isochaetominine C (6). The 1H and 13C NMR data of compound 6 matched those of natural aspera chaetominine B suggesting that aspera chaetominine B is
Bioinspired total syntheses of natural products: a personal adventure
Beilstein J. Org. Chem. 2025, 21, 2048–2061, doi:10.3762/bjoc.21.160
- catalytic asymmetric methods [26], we intended to probe this biomimetic oxidative cyclization transformation [27][28]. In 2013, we first used monocerin as a model target molecule to initiate our study (Scheme 3a). Starting from benzaldehyde 11 with an isopropyl group on the hydroxy group in 4-position
- underwent dehydroxylation protocol involving base-promoted mesylate elimination and catalytic hydrogenation reactions, providing 31a. Reduction of lactam and ester in one pot with LiAlH4 and acid-promoted hydrolysis of ketal protection to ketone furnished 32a. Finally, oxidation of the primary alcohol to
- material of the amine was directly treated with cinnamoyl chloride under basic conditions to install the cinnamoyl side chain, delivering natural products sarglamides A and C independently. Sarglamide C was exposed to an acid to access sarglamides D and E with an oxyl-bridge. When a catalytic amount of
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