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Search for "evolution" in Full Text gives 332 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Novel macrocycles: from synthesis to supramolecular function
Beilstein J. Org. Chem. 2026, 22, 982–985, doi:10.3762/bjoc.22.76
- versatile tools for the selective modulation of biologically relevant protein–protein interactions. The contributions collected in this thematic issue highlight the breadth and continued evolution of contemporary macrocyclic chemistry. From new ultracycle receptors to functional materials for carbon dioxide
Electrochemical reduction of unsaturated carbon–carbon bonds via 3d transition-metal catalysis
Beilstein J. Org. Chem. 2026, 22, 955–981, doi:10.3762/bjoc.22.75
- electrochemical conditions, coupled with the propensity of such intermediates to promote undesired hydrogen evolution in the presence of proton sources. In 2025, the Derosa group systematically evaluated the feasibility of electroreductive iron catalysis using alkyne semihydrogenation as a model transformation
- tolerated (Scheme 1B). Cyclic voltammetric studies revealed distinct Fe(II/I) and Fe(I/0) redox events for (P3P)Fe(II)(BF4)2. Notably, introduction of cobaltocene (Cp2Co) as a redox mediator enabled selective SET at a more anodic potential, thereby suppressing competitive hydrogen evolution and rendering
- exhibiting remarkably broad functional group tolerance, even in the presence of readily reducible functionalities (Scheme 4B). Also, the use of a redox mediator allows operation at a milder applied potential, thereby suppressing overreduction pathways and competitive hydrogen evolution while maintaining high
Synthesis of sterically shielded piperidine nitroxides via acid-catalyzed heterocyclization of β-aminoketone derivatives with ketones
Beilstein J. Org. Chem. 2026, 22, 948–954, doi:10.3762/bjoc.22.74
- evolution, methanesulfonic acid (2.0 equiv) was added dropwise to the refluxing mixture, and heating was continued for an additional hour. The reaction was quenched with aqueous sodium carbonate, and the resulting piperidines 5a,b were purified by vacuum distillation. The target 2,2,6-triethyl- and 2,2,6
Site-specific labelling of native peptides and proteins: chemical and enzymatic strategies
Beilstein J. Org. Chem. 2026, 22, 857–881, doi:10.3762/bjoc.22.67
- penicillin G acylase (PGA) for the selective modification of insulin [151]. After screening 100 commercially available PGA homologs and initial optimisation for expression and handling, Kluyvera cryocrescens PGA was chosen for directed evolution (Scheme 15b). The goal was to selectively protect or deprotect
Using generative AI to transform peptide hits into small molecule leads
Beilstein J. Org. Chem. 2026, 22, 672–679, doi:10.3762/bjoc.22.51
- ), including RFdiffusion2 [43] and RFdiffusion3 [44], along with integrated pipelines such as BindCraft [31] which are built upon tools such as ProteinMPNN and AlphaFold2. Other design tools that are specific for peptide binders also include the evolution-based EvoBind2 that only requires the protein target
Hydrogen production from formic acid catalyzed by NHC–Cu complexes
Beilstein J. Org. Chem. 2026, 22, 620–627, doi:10.3762/bjoc.22.48
- . Interestingly, by adding to the reaction mixture a further equivalent of FA, evolution of gas was observed and H2 was detected by NMR spectroscopy (see Supporting Information File 1, Figure S1). This highlighted the formation in situ of the Cu–H species by decarboxylation of 1b. To quantify the amount of gas
- produced, the pressure change was measured as a function of time (see Supporting Information File 1, Table S1). By heating formic acid in toluene in the presence of 1 and 10 mol % of 1a, no evolution of gas was observed neither at 25 nor at 110 °C (see Supporting Information File 1, Table S1, entries 1–4
- our delight, upon reacting in toluene equimolar amounts of FA and PhSiH3, efficiency increased (Figure 2). Indeed, by using 1a and its tert-butoxide congener 1c ([Cu] = 10 mol %) a violent evolution of gas was observed at room temperature, resulting into a considerable increase of pressure which
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
- contain complex three-dimensional structures, make total synthesis challenging. The retrosynthetic analysis [9], alongside the evolution of methodologies such as “two-phase synthesis” [10], “biomimetic synthesis” [11], or “protecting-group-free synthesis” [12], has progressively streamlined synthetic
- with exceptional step and atom economy has begun to reshape how to design synthetic routes toward architecturally complex natural products. The past five years have witnessed significant methodological evolution in the hydrogenation of (hetero)arenes. However, a systematic analysis correlating catalyst
Recent advancements in the synthesis of Veratrum alkaloids
Beilstein J. Org. Chem. 2025, 21, 2657–2693, doi:10.3762/bjoc.21.206
- functionalization for rapid access to these exceptional alkaloids, while also showcasing the evolution of the art of synthesis and its ability in meeting the demands posed by molecular complexity. Keywords: alkaloid synthesis; convergent synthesis; total synthesis; Veratrum alkaloids; Introduction Veratrum
- embedded in A–E rings, thus, adding to their complexity in total synthesis efforts [9]. This review will cover synthetic approaches from the last decades, showcasing the evolution of Veratrum alkaloids synthesis and by that, providing an impression of the evolution of synthetic methods in general. For a
- simultaneously. Notably, both total syntheses commenced from (S)-Wieland–Miescher ketone, but made the retrosynthetic cut elsewhere in the molecule (Baran: D-ring, Zhu/Gao: C-ring). In comparison, a direct evolution can be seen from 2009 to 2024. While the first synthesis of cyclopamine by Giannis [21] stood
Isoorotamide-based peptide nucleic acid nucleobases with extended linkers aimed at distal base recognition of adenosine in double helical RNA
Beilstein J. Org. Chem. 2025, 21, 2513–2523, doi:10.3762/bjoc.21.193
- hydrogen bonding (blue dashed lines). Watson–Crick hydrogen bonds are in red (dashed lines). Evolution of the strategy for U–A recognition. Isoorotamide-derived nucleobases for A–U recognition. Proposed isoorotamide distal binding (Db) nucleobases designed from the Io5 core. Hydrogen bonding donors to the
C2 to C6 biobased carbonyl platforms for fine chemistry
Beilstein J. Org. Chem. 2025, 21, 2103–2172, doi:10.3762/bjoc.21.165
- temperatures between 180–240 ºC in a maximum yield of about 30–40% (Scheme 14) [72][73]. Dihydroxyacetone (DHA) The formose process is the conversion of formaldehyde to glycolaldehyde and 1,3-dihydroxy-2-propanone (dihydroxyacetone, DHA). A computational protein-directed evolution allowed to create "formolase
Bioinspired total syntheses of natural products: a personal adventure
Beilstein J. Org. Chem. 2025, 21, 2048–2061, doi:10.3762/bjoc.21.160
- biotic evolution in which live survives from changes of Earth environment by changing themselves. Natural products play a pivotal role in biological transformations within organisms, and moreover, are of great value for human life by serving as food, cloth and medicine. It represents a longstanding goal
Understanding the origin of stereoselectivity in the photochemical denitrogenation of 2,3-diazabicyclo[2.2.1]heptene and its derivatives with non-adiabatic molecular dynamics
Beilstein J. Org. Chem. 2025, 21, 2007–2020, doi:10.3762/bjoc.21.156
- producing energy-dense compounds [2][3]. One promising strategy to access strained compounds involves gas-evolution (e.g., CO or N2) because of the associated entropic driving force; this approach has had wide utility in photomedicine and organic synthesis. For example, photochemical decarboxylation has
Chiral phosphoric acid-catalyzed asymmetric synthesis of helically chiral, planarly chiral and inherently chiral molecules
Beilstein J. Org. Chem. 2025, 21, 1864–1889, doi:10.3762/bjoc.21.145
- asymmetric Mannich reactions, the past two decades have witnessed the remarkable evolution of CPA catalysis into one of the most versatile platforms for achieving diverse enantioselective transformations [3][4][5][6][7][8]. CPA catalysts are generally recognized as bifunctional catalysts with two distinct
Transition-state aromaticity and its relationship with reactivity in pericyclic reactions
Beilstein J. Org. Chem. 2025, 21, 1613–1626, doi:10.3762/bjoc.21.125
- [1][2][3]. Initially introduced to account for the remarkable stability, low reactivity, and unique structural features of benzene and related aromatic hydrocarbons, the concept has undergone a significant evolution [4]. Since the introduction of the famous Hückel’s (4n + 2) rule [5], first clearly
- ) value (ca. −20 ppm) [67]. Not surprisingly, the analogous, uncatalyzed carbonyl–ene reaction features a similar TS-aromaticity as confirmed by the evolution of the NICS values along a z-axis perpendicular to the molecular plane which exhibits the bell-shape expected for an in-plane aromatic molecule [45
- cycloadditions involving metal cyaphides should be in-plane aromatic species due to the cyclic delocalization of 6-electrons in the molecular plane. Indeed, the evolution of the NICS(3, +1) values along a z-axis perpendicular to the molecular plane shows the expected bell shape with a maximum value at z = 0 Å
Thermodynamic equilibrium between locally excited and charge transfer states in perylene–phenothiazine dyads
Beilstein J. Org. Chem. 2025, 21, 1577–1586, doi:10.3762/bjoc.21.121
- to resolve into the evolution-associated spectra (EAS) [19]. The spectral evolution over time was tentatively analyzed using a three- or four-component sequential decay model (for example, the four-state kinetic model is described as EAS1 → EAS2 → EAS3 → EAS4 → ground state). Figure 6a and 6c show
- . Microsecond transient absorption (a) spectra and (b) dynamics of Pe–PTZ(TPA)2 in benzene excited at 355 nm (5 μJ/pulse) and probed at 430 nm under nitrogen and oxygen conditions. Femtosecond-to-nanosecond transient absorption spectra and evolution-associated spectra (EAS) of Pe–PTZ(TPA)2 in benzene excited at
- (a, c) 350 nm (20 nJ/pulse) and (b, d) 420 nm (6 nJ/pulse) at room temperature. (a) Femtosecond-to-nanosecond transient absorption spectra and (b) evolution-associated spectra (EAS) of Pe–Ph–PTZ(TPA)2 in benzene excited at 350 nm (20 nJ/pulse) at room temperature. Summarized photophysical process of
Ambident reactivity of enolizable 5-mercapto-1H-tetrazoles in trapping reactions with in situ-generated thiocarbonyl S-methanides derived from sterically crowded cycloaliphatic thioketones
Beilstein J. Org. Chem. 2025, 21, 1508–1519, doi:10.3762/bjoc.21.113
- slightly higher temperature (60 °C). In both cases, evolution of nitrogen was completed after ca. 3 h and pure thiiranes 8a and 8b were isolated as sole products in 62%, and 58% yield, respectively (Scheme 4). Thus, their formation clearly evidenced formation of the respective thiocarbonyl S-methanides 1c
- was typically carried out at 45 °C in THF solution, and evolution of N2 was monitored using a nitrometer connected with the reaction flask. When the evolution of the gas was completed, the solvent was evaporated, and the crude residue was checked by means of 1H NMR. Two high-field shifted singlets
- decomposition of dispiro-1,3,4-thiadiazoline 2c: A magnetically stirred solution of 2c (125.0 mg, 0.5 mmol) in 1 mL THF was heated in an oil bath at 65 °C and the evolution of nitrogen gas was controlled with a nitrometer (gas burette) connected with the flask. After ca. 3 h evolution of nitrogen was complete
On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals
Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80
- electron paramagnetic resonance (EPR). This enables improved homogeneity in quantum phase evolution and superior Tm, rendering brominated trityl radicals interesting for quantum memory applications [55]. Symmetry in N-heteroaryl-functionalized diphenylmethyl radicals Another approach to affect the symmetry
Recent advances in controllable/divergent synthesis
Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73
- or stimulus-responsive approaches, this paradigm capitalizes on the chronoselective evolution of reactive species to unlock sequence-controlled transformations. In 2020, the You group reported a reaction-time-dependent enantiodivergent synthesis method. Under the same chiral catalytic system, they
Recent advances in allylation of chiral secondary alkylcopper species
Beilstein J. Org. Chem. 2025, 21, 639–658, doi:10.3762/bjoc.21.51
- nucleophiles 5 that have conjugate acids with pKa values greater than 25 such as organolithium, organomagnesium, organozinc, and organozirconium reagents. This crucial distinction effectively expanded the scope of allylic substitution reactions beyond traditional boundaries. The evolution of copper-catalyzed
- mechanistic insight into the observed stereochemical outcome. Conclusion This review highlights the evolution of strategies for generating and utilizing chiral nonracemic organocopper species with secondary carbon–metal bonds in asymmetric allylic substitution reactions. Early approaches relied on the
Entry to 2-aminoprolines via electrochemical decarboxylative amidation of N‑acetylamino malonic acid monoesters
Beilstein J. Org. Chem. 2025, 21, 630–638, doi:10.3762/bjoc.21.50
- undesired cathodic reduction. Indeed, trace amounts of 2-aminoproline derivative 6g (<4%) could be obtained by replacing SS as the cathode material with platinum that has a low overpotential for hydrogen evolution reaction [14]. To avoid the undesired cathodic reduction of the nitro group, the electrolysis
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
- reagents (“cofactors”), they could perform non-biotic reactions, and even have potential for the design of novel active sites that could be transposed into new designer enzymes for optimization [388][389][390][391], since directed evolution requires initial activity to work from. Flexibility vs rigidity
Red light excitation: illuminating photocatalysis in a new spectrum
Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22
- growing concerns around environmental sustainability, there is increasing interest in developing photocatalysts that are more accessible, tunable, and eco-friendly. Each section of this document discusses a specific approach to red-light photocatalysis, reflecting the field’s evolution and exploring
- efficient catalytic processes. In the same way, recent advances in red-light photoredox catalysis have expanded the utility of first-row transition metals in a domain traditionally dominated by second- and third-row elements. A prime example of this evolution is the development of a dual photoredox strategy
Oxidation of [3]naphthylenes to cations and dications converts local paratropicity into global diatropicity
Beilstein J. Org. Chem. 2025, 21, 277–285, doi:10.3762/bjoc.21.20
- Supporting Information File 1). Upon second oxidation, the former Raman vibrational band upshifts by 24 cm−1 for 12+, and the naphthalene ν(CC)NAP stretching one disappears. Overall, the evolution of the CBD breathing mode, throughout the series 1→1•+→12+ is 1700 → 1689 → 1713 cm−1. Figure 5 shows the Raman
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
- stations for consumables and sample storage. Remarkably, through a tedious ten-dimensional parameter search spanning eight days, the robot achieved an impressive hydrogen evolution rate of approximately 21.05 µmol⋅h−1. Despite the initial investment and two-year development timeline, the versatility of
- chromatographic spectra and to automatically assign the peaks to reagents or products depending on the decrease or increase in peak intensity over time. In addition to monitoring the evolution of the reaction, the IR spectral data was processed in real time. This was to ensure the complete consumption of acid
Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies
Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261
- ]. In relation to epilepsy, the etiology of seizures depends on age. In children, seizures are frequently originated by genetic factors, malformations of cortical evolution, and injuries from perinatal events. In adults lacking an inherited tendency, typical causes include encephalitis or meningitis
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