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

• are important intermediates in organic syntheses because of the versatility of the cyano group, which can be readily transformed into a wide range of functional groups, including amides, carboxylic acids, amines, aldehydes, ketones, and N-heterocycles [6][7][8]. However, the synthesis of all-carbon

• with diverse functional groups [12][13][14]. Consequently, the development of selective and predictable strategies for the introduction of cyano groups into quaternary carbon frameworks has become necessary in organic synthesis. The transition-metal-catalyzed hydrocyanation of carbon–carbon double

Carbon-rich materials: from polyaromatic molecules to fullerenes and other carbon allotropes

• Hiroko Yamada and
• Yoko Yamakoshi

Beilstein J. Org. Chem. 2025, 21, 798–799, doi:10.3762/bjoc.21.62

• on carbon-rich materials. We highly appreciate that so many of our colleagues and friends – researchers with a variety of backgrounds working on these special molecules – agreed to contribute to this project. The authors hail from diverse research areas, including synthetic organic chemistry, surface

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

• of organic compounds. In recent years, many advances have been made in this field of research, and researchers have been able to synthesize many compounds and confirm various uses for chemical compounds in this field. The significant progress in this field of research led to the name of this field as

• that controls reaction selectivity by adjusting voltage or current [13]. Simple synthetic systems in electrochemical methods are limited to electrodes, cells, electrolytes, and power supplies. Today, in addition to the above, light, metallic, and organic catalysts are also used to increase the

• reaction. Some of their applications include hydrogen and oxygen production, metal electroplating, and organic compound synthesis using electrochemical methods. Depending on the reaction conditions, these cells can be divided or undivided. Divided vs undivided cells In divided cells, oxidation and

New advances in asymmetric organocatalysis II

• Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 766–769, doi:10.3762/bjoc.21.60

• Radovan Sebesta Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia 10.3762/bjoc.21.60 Keywords: asymmetric organocatalysis; covalent activation; noncovalent activation; Organocatalysis is

• commonly defined as a form of catalysis where a small organic molecule, an organocatalyst, accelerates a chemical reaction. Unlike previously regarded traditional catalysts involving metals or enzymes, organocatalysts are composed of nonmetal elements, such as carbon, hydrogen, nitrogen, oxygen, phosphorus

• as the eco- and user-friendliness of asymmetric organocatalysis contribute to its growing applicability in the synthesis of complex target molecules, such as therapeutic agents [17][18]. However, nowadays organocatalysis does go well beyond the boundaries of organic chemistry. This can also be seen

Development and mechanistic studies of calcium–BINOL phosphate-catalyzed hydrocyanation of hydrazones

• Carola Tortora,
• Christian A. Fischer,
• Sascha Kohlbauer,
• Alexandru Zamfir,
• Gerd M. Ballmann,
• Jürgen Pahl,
• Sjoerd Harder and
• Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2025, 21, 755–765, doi:10.3762/bjoc.21.59

• Carola Tortora Christian A. Fischer Sascha Kohlbauer Alexandru Zamfir Gerd M. Ballmann Jurgen Pahl Sjoerd Harder Svetlana B. Tsogoeva Department of Chemistry and Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität

Orthogonal photoswitching of heterobivalent azobenzene glycoclusters: the effect of glycoligand orientation in bacterial adhesion

• Leon M. Friedrich and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2025, 21, 736–748, doi:10.3762/bjoc.21.57

• Leon M. Friedrich Thisbe K. Lindhorst Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3–4, 24118 Kiel, Germany 10.3762/bjoc.21.57 Abstract Carbohydrate recognition is fundamental to a plethora of cellular processes and hence the elucidation of

• . Supporting Information File 1, Figures S13–S16). DMSO is known for its bactericidal effect and still, the use of this organic solvent in bioassays is common [42]. In general, a DMSO concentration of less than 10% (v/v) is accepted as nontoxic [43]. In any case, the effect of DMSO in the assays was carefully

Synthesis of HBC fluorophores with an electrophilic handle for covalent attachment to Pepper RNA

• Raphael Bereiter and
• Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 727–735, doi:10.3762/bjoc.21.56

• Raphael Bereiter Ronald Micura Institute of Organic Chemistry, Center for Molecular Biosciences, Innsbruck (CMBI), University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria 10.3762/bjoc.21.56 Abstract The fluorescent light-up aptamer (FLAP) Pepper can utilize fluorophores that are equipped

Acyclic cucurbit[n]uril bearing alkyl sulfate ionic groups

• Christian Akakpo,
• Peter Y. Zavalij and
• Lyle Isaacs

Beilstein J. Org. Chem. 2025, 21, 717–726, doi:10.3762/bjoc.21.55

• elements of life processes including self- versus non-self-recognition, biosynthesis, molecular and ion transport, and replication. Beginning with the pioneering works of Pedersen, Lehn, and Cram, supramolecular chemists have studied the fundamental aspects of non-covalent interactions in organic solvents

Origami with small molecules: exploiting the C–F bond as a conformational tool

• Patrick Ryan,
• Ramsha Iftikhar and
• Luke Hunter

Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54

• Patrick Ryan Ramsha Iftikhar Luke Hunter School of Chemistry, The University of New South Wales (UNSW), Sydney 2052, Australia 10.3762/bjoc.21.54 Abstract When present within an organic molecule, the C–F bond tends to align in predictable ways with neighbouring functional groups, due to

• compact size of the fluorine atom itself, means that fluorine can be incorporated into an organic molecule as a replacement for hydrogen without drastically altering the molecular volume. Second, the C–F bond is highly polarised. This means that any molecular conformation in which the C–F dipole is

• concepts to their own scaffolds of interest. Review 1 Alkanes The simplest organic scaffolds are the alkanes. In such molecules, C–C bond rotations often have low energy barriers, and they often deliver conformers that are similar in energy, and this means that many alkanes have considerable conformational

Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra

• Yuuki Ishii,
• Minoru Yamaji,
• Fumito Tani,
• Kenta Goto,
• Yoshihiro Kubozono and
• Hideki Okamoto

Beilstein J. Org. Chem. 2025, 21, 670–679, doi:10.3762/bjoc.21.53

• chemistry, but also for their application in materials science, in particular, in organic electronics [1][2][3][4]. Among the structural classifications of PAHs, the representatives are acenes and phenacenes; the former consisting of linearly fused benzene-ring arrays while the latter exhibit zigzag ones

• due to the angular annelation. These series are known as one-dimensional graphene ribbons. As has been commonly recognized, acene molecules have been intensively and extensively studied in the organic functional materials field [5][6][7]. By contrast, phenacenes had been hardly applied as functional

• molecules in spite of their long history; phenacenes were recognized as contents in petroleum-industry residues as early as in the 19th century [8][9]. In the last decade, phenacenes were demonstrated to serve as platform materials namely in organic electronics, such as chromophores for photovoltaics [10

Asymmetric synthesis of fluorinated derivatives of aromatic and γ-branched amino acids via a chiral Ni(II) complex

• Maurizio Iannuzzi,
• Thomas Hohmann,
• Michael Dyrks,
• Kilian Haoues,
• Katarzyna Salamon-Krokosz and
• Beate Koksch

Beilstein J. Org. Chem. 2025, 21, 659–669, doi:10.3762/bjoc.21.52

• , base, solvent, and reagent equivalents to optimize the alkylation reaction for both bromides 4 and 5 (Table 1 and Table 2). For Ni(II) complex of [2.3.5.6F]TfMePhe (6), firstly we screened different inorganic and organic bases (Table 1, entries 1–3) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was

• with DCM (2 × 40 mL). The combined organic phases were then washed with aq HCl (2 M, 12 mL), saturated aqueous NaHCO3 solution (12 mL), and brine (12 mL). Afterward, the combined organic phases were dried over Na2SO4, filtered, and dried in vacuo for 16 h. The crude product was purified via flash

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

• Abstract The transition-metal-catalyzed asymmetric allylic substitution represents a pivotal methodology in organic synthesis, providing remarkable versatility for complex molecule construction. Particularly, the generation and utilization of chiral secondary alkylcopper species have received considerable

• 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

• AAA methodologies. Review Copper-catalyzed stereospecific coupling of chiral organometallic species with allylic electrophiles The asymmetric construction of carbon–carbon bonds through copper-catalyzed AAA has emerged as a powerful synthetic tool in organic chemistry [41][42][43][44][45]. The

Entry to 2-aminoprolines via electrochemical decarboxylative amidation of N‑acetylamino malonic acid monoesters

• Olesja Koleda,
• Janis Sadauskis,
• Darja Antonenko,
• Edvards Janis Treijs,
• Raivis Davis Steberis and
• Edgars Suna

Beilstein J. Org. Chem. 2025, 21, 630–638, doi:10.3762/bjoc.21.50

• Olesja Koleda Janis Sadauskis Darja Antonenko Edvards Janis Treijs Raivis Davis Steberis Edgars Suna Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga LV-1006, Latvia Faculty of Medicine and Life Sciences, Department of Chemistry, University of Latvia, Jelgavas 1, Riga LV-1004, Latvia

Photocatalyzed elaboration of antibody-based bioconjugates

• Marine Le Stum,
• Eugénie Romero and
• Gary A. Molander

Beilstein J. Org. Chem. 2025, 21, 616–629, doi:10.3762/bjoc.21.49

• aqueous media is essential for the modification of antibodies, as these biomolecules are typically dissolved in water or aqueous buffers to maintain their stability and activity. Antibodies are sensitive to their environment, and using a non-negligible amount of organic solvents or harsh chemical

Semisynthetic derivatives of massarilactone D with cytotoxic and nematicidal activities

• Rémy B. Teponno,
• Sara R. Noumeur and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 607–615, doi:10.3762/bjoc.21.48

• mixture was stirred at room temperature overnight. The reaction mixture was suspended in water (25 mL) and extracted with CH2Cl2 (2 × 25 mL). The combined organic layer was evaporated to dryness to give a residue, which was dissolved in methanol (300 μL) and purified by preparative HPLC [ChemStation

• (25 mL) and extracted with CH2Cl2 (2 × 25 mL). The combined organic layer was evaporated to dryness to give a residue, which was dissolved in methanol (300 μL) and purified by preparative HPLC (gradient from 60 to 85% solvent B in 50 min) to yield compounds 3 in 6% yield (1.72 mg, tR = 25.24 min) and

• with CH2Cl2 (2 × 25 mL). The combined organic layer was evaporated to dryness to give a residue, which was dissolved in methanol (300 μL) and purified by preparative HPLC (gradient from 60 to 100% solvent B in 50 min) to yield compound 5 in 82% yield (39.79 mg, tR = 22.50 min). White powder; [α]D25

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

• mixture was neutralized to pH 7 using saturated sodium bicarbonate solution and extracted with ethyl acetate multiple times. The organic extracts were combined, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to afford H2d as a white solid. Yield 70%. 1H NMR (400 MHz, DMSO-d6

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

• concerns and improved reaction control can be addressed, paving the way for more efficient and sustainable synthetic methodologies. Keywords: cascade reactions; formaldehyde surrogates; green chemistry; heterocycles; multicomponent reactions; Introduction Organic chemistry is a mature discipline that has

• undergone significant changes since the term was first coined. Since its inception, organic chemistry has straddled the boundaries between art, creativity, and industrial applications. It is a science that is needed to solve complex retrosynthetic problems and develop molecules in gram to kilogram scales

• surrogate and source of formaldehyde Dimethyl sulfoxide is a well-known polar-aprotic solvent with high boiling point that is used in several organic synthetic reactions because of affordable cost and relatively low toxicity. There are numerous examples that show the use of DMSO as a C1 or C2 building block

Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles

• Constantine V. Milyutin,
• Andrey N. Komogortsev and
• Boris V. Lichitsky

Beilstein J. Org. Chem. 2025, 21, 556–563, doi:10.3762/bjoc.21.44

• Constantine V. Milyutin Andrey N. Komogortsev Boris V. Lichitsky N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation 10.3762/bjoc.21.44 Abstract For the first time, the reaction of substituted 2H-furo[3,2-b]pyran-2-ones

• Supporting Information File 2: General information, characterization data, NMR spectra and crystallographic data of synthesized compounds. Acknowledgements Crystal structure determination was performed in the Department of Structural Studies of Zelinsky Institute of Organic Chemistry, Moscow.

Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt

• Yasushi Yoshida,
• Maho Aono,
• Takashi Mino and
• Masami Sakamoto

Beilstein J. Org. Chem. 2025, 21, 547–555, doi:10.3762/bjoc.21.43

• of its unique interaction in organic synthesis. Chiral halonium salts have been found to have strong halogen-bonding-donor abilities and work as powerful asymmetric catalysts. Recently, we have developed binaphthyl-based chiral halonium salts and applied them in several enantioselective reactions

• organic chemistry [2][3][4][5], organocatalysis [6][7], metal catalysis [8][9], biochemistry [10][11], materials science [12][13], and supramolecular chemistry [14][15], although its successful application to asymmetric catalysis has been limited (Figure 1) [16][17][18][19][20]. In 2018, Arai and co

Binding of tryptophan and tryptophan-containing peptides in water by a glucose naphtho crown ether

• Gianpaolo Gallo and
• Bartosz Lewandowski

Beilstein J. Org. Chem. 2025, 21, 541–546, doi:10.3762/bjoc.21.42

• Gianpaolo Gallo Bartosz Lewandowski Laboratory of Organic Chemistry, ETH Zürich, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland 10.3762/bjoc.21.42 Abstract Tryptophan fulfills a plethora of important functions in nature both in its free form and as a component of peptides and proteins. Selective

Cryptophycin unit B analogues

• Thomas Schachtsiek,
• Jona Voss,
• Maren Hamsen,
• Beate Neumann,
• Hans-Georg Stammler and
• Norbert Sewald

Beilstein J. Org. Chem. 2025, 21, 526–532, doi:10.3762/bjoc.21.40

• Thomas Schachtsiek Jona Voss Maren Hamsen Beate Neumann Hans-Georg Stammler Norbert Sewald Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, Universitätsstraße 25, 33615 Bielefeld, Germany Department of Chemistry, Inorganic and Structural Chemistry, Bielefeld

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

• ; perfluorobenzylation; photochemistry; Introduction The revolution of small organic molecules in the semiconductor industry continues to progress, replacing some silicon and metal-based electronic components. Acenes, such as anthracene (ANTH) and its higher homologues, represent some of the most studied materials that

• have promising applications in optoelectronics. For example, investigation of the photophysical and electronic properties of ANTH began in the 1960s [1][2][3], and since then many new ANTH derivatives have been synthesized and explored for their use as fluorescent probes, organic semiconductors, and

• emitters for organic light emitting diodes (OLEDs) [4][5][6][7][8]. More recently, an increased interest in the studies of triplet–triplet annihilation mechanisms in anthracene emitter materials [9] and the design of efficient OLED emitters based on hyperfluorescence [10][11], which could exhibit high

Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye

• Metodej Dvoracek,
• Brendan Twamley,
• Mathias O. Senge and
• Mikhail A. Filatov

Beilstein J. Org. Chem. 2025, 21, 500–509, doi:10.3762/bjoc.21.37

• topochemical reactions. Currently, topochemically active monomers are limited to large, planar aromatic molecules, aryl-substituted olefins, and polyenes, often complexed with metals. These compounds are frequently employed in the construction of metal-organic frameworks [13][14][15]. The limited range of

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

• Thomas Brandt Pascal Lentes Jeremy Rudtke Michael Hosgen Christian Nather Rainer Herges Otto Diels Institute for Organic Chemistry, Kiel University, Otto-Hahn-Platz 4, 24118 Kiel, Germany Institute for Inorganic Chemistry, Kiel University, Max-Eyth-Straße 2, 24118 Kiel, Germany 10.3762/bjoc.21.36

• ]. Moreover, the parent diazocine is insoluble in water (precipitation in water/DMSO > 9:1). Substitution with polar substituents such as CH2NH2 provides water solubility, however, it does not restore the high Z → E conversion rates of the parent system in organic solvents, which is a disadvantage, since

• azobenzenes, spiropyranes and diarylethenes in organic solvents [3][13][15]. There are two strategies of applying diazocines in photopharmacology. The first one exploits the structural similarity of the tricyclic diazocine framework to the tricyclic structure of, e.g., tetrahydrodibenzazocines [16][17] and

Synthesis of electrophile-tethered preQ₁ analogs for covalent attachment to preQ₁ RNA

• Laurin Flemmich and
• Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35

• Laurin Flemmich Ronald Micura Institute of Organic Chemistry, Center for Molecular Biosciences Innsbruck (CMBI), Innrain 80-82, 6020 Innsbruck, Austria 10.3762/bjoc.21.35 Abstract The preQ1 cIass-I riboswitch aptamer can utilize 7-aminomethyl-7-deazaguanine (preQ1) ligands that are equipped with

• derivatives have been reported [22][23][24][25][26]. Among these reports, various silylation and protection strategies have been employed to address the poor solubility of preQ1 (and analogs) in organic solvents [9][22][23][25][26][27][28][29]. Herein, we report an optimized three-step protocol, free of