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

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

• 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

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

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

• 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

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

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

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

• research. Keywords: light-mediated synthesis; mechanochemistry; photomechanochemistry; Introduction Light-mediated synthetic methodologies have significantly transformed contemporary organic chemistry by enabling a broad array of previously unattainable transformations [1]. In fact, the absorption of a

New tandem Ugi/intramolecular Diels–Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives

• Yuriy I. Horak,
• Roman Z. Lytvyn,
• Andrii R. Vakhula,
• Yuriy V. Homza,
• Nazariy T. Pokhodylo and
• Mykola D. Obushak

Beilstein J. Org. Chem. 2025, 21, 444–450, doi:10.3762/bjoc.21.31

• Yuriy I. Horak Roman Z. Lytvyn Andrii R. Vakhula Yuriy V. Homza Nazariy T. Pokhodylo Mykola D. Obushak Department of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005, Ukraine 10.3762/bjoc.21.31 Abstract A new tandem sequence involving the Ugi

Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones

• Yurii A. Sayapin,
• Eugeny A. Gusakov,
• Inna O. Tupaeva,
• Alexander D. Dubonosov,
• Igor V. Dorogan,
• Valery V. Tkachev,
• Anna S. Goncharova,
• Gennady V. Shilov,
• Natalia S. Kuznetsova,
• Svetlana Y. Filippova,
• Tatyana A. Krasnikova,
• Yanis A. Boumber,
• Alexey Y. Maksimov,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26

• Research Centre the Southern Scientific Centre of the Russian Academy of Sciences, Rostov-on-Don 344006, Russian Federation Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don 344090, Russian Federation Federal Research Center of Problems of Chemical Physics and Medical

Synthesis of new condensed naphthoquinone, pyran and pyrimidine furancarboxylates

• Kirill A. Gomonov,
• Vasilii V. Pelipko,
• Igor A. Litvinov,
• Ilya A. Pilipenko,
• Anna M. Stepanova,
• Nikolai A. Lapatin,
• Ruslan I. Baichurin and
• Sergei V. Makarenko

Beilstein J. Org. Chem. 2025, 21, 340–347, doi:10.3762/bjoc.21.24

• Kirill A. Gomonov Vasilii V. Pelipko Igor A. Litvinov Ilya A. Pilipenko Anna M. Stepanova Nikolai A. Lapatin Ruslan I. Baichurin Sergei V. Makarenko Department of organic chemistry, Herzen State Pedagogical University of Russia, nab. r. Moiki 48, 191186 St. Petersburg, Russian Federation Federal

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

• , red-light photocatalysis enables innovative applications in phototherapy and controlled drug release, exploiting its tissue penetration and low cytotoxicity. Together, these developments underscore the versatility and impact of red-light photocatalysis, positioning it as a cornerstone of green organic

• chemistry with significant potential in synthetic and biomedical fields. Keywords: green chemistry; medicinal chemistry; organic photochemistry; photocatalysis; red-light mediated transformations; Introduction Red-light-activated photocatalysis has recently gained significant interest as a tool for

Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide

• Marios Zingiridis,
• Danae Papachristodoulou,
• Despoina Menegaki,
• Konstantinos G. Froudas and
• Constantinos G. Neochoritis

Beilstein J. Org. Chem. 2025, 21, 217–225, doi:10.3762/bjoc.21.13

• such, it is becoming increasingly essential for synthetic methods to align with a net-zero carbon future [2][3]. Therefore, advancing C1 chemistry remains a crucial endeavor for our group [4]. In synthetic organic chemistry, C1 compounds are usually installed using CO, CO2, HCO2H, CH3OH and CH4, which

• of aliphatic and aromatic substituents (Scheme 4). Pyrimidines and pyrimidone-bearing indole derivatives are crucial in organic chemistry because of their extensive use as bioactive compounds with a wide array of significant biological activities (DB03074, DB03304, DB08131) [70][71][72]. In a similar

Nickel-catalyzed cross-coupling of 2-fluorobenzofurans with arylboronic acids via aromatic C–F bond activation

• Takeshi Fujita,
• Haruna Yabuki,
• Ryutaro Morioka,
• Kohei Fuchibe and
• Junji Ichikawa

Beilstein J. Org. Chem. 2025, 21, 146–154, doi:10.3762/bjoc.21.8

• organic chemistry owing to their high bond dissociation energy compared to other aromatic C–X (X = Cl, Br, I) bonds [1][2][3][4][5][6][7]. This activation is essential for the late-stage functionalization of stable C–F bonds in complex molecules with reactive functional groups, providing an orthogonal

Recent advances in organocatalytic atroposelective reactions

• Henrich Szabados and
• Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

• Henrich Szabados Radovan Sebesta Department of Organic Chemistry, Faculty of Natural Science, Comenius University Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia 10.3762/bjoc.21.6 Abstract Axial chirality is present in a variety of naturally occurring compounds, and is

Emerging trends in the optimization of organic synthesis through high-throughput tools and machine learning

• Pablo Quijano Velasco,
• Kedar Hippalgaonkar and
• Balamurugan Ramalingam

Beilstein J. Org. Chem. 2025, 21, 10–38, doi:10.3762/bjoc.21.3

• commercial and in-house developed equipment. Normally, HTE for organic chemistry will include a liquid transfer module, a reactor stage, and analytical tools for product characterization. When the full experimental process is automated and coupled with a centralized control system performing ML optimization

Giese-type alkylation of dehydroalanine derivatives via silane-mediated alkyl bromide activation

• Perry van der Heide,
• Michele Retini,
• Fabiola Fanini,
• Giovanni Piersanti,
• Francesco Secci,
• Daniele Mazzarella,
• Timothy Noël and
• Alberto Luridiana

Beilstein J. Org. Chem. 2024, 20, 3274–3280, doi:10.3762/bjoc.20.271

• ; Introduction The construction of C(sp3)–C(sp3) bonds is a highly important target in synthetic organic chemistry. Historically, polar conjugate additions have been a benchmark method for constructing these bonds by functionalizing an electron-deficient olefin [1][2][3]. Recently, however, radical-based

Intramolecular C–H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds

• Yuki Nakanishi,
• Shoichi Sugita,
• Kentaro Okano and
• Atsunori Mori

Beilstein J. Org. Chem. 2024, 20, 3256–3262, doi:10.3762/bjoc.20.269

• ; phosphine ligand; pyridine amides; Introduction Transition-metal-catalyzed synthetic reactions have recently attracted much attention in synthetic organic chemistry [1][2]. C–H Arylation reactions catalyzed by a transition metal are of particular interest because these reactions involve rather superior

Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds

• Radell Echemendía,
• Carlee A. Montgomery,
• Fabio Cuzzucoli,
• Antonio C. B. Burtoloso and
• Graham K. Murphy

Beilstein J. Org. Chem. 2024, 20, 3182–3190, doi:10.3762/bjoc.20.263

• of compounds, increase their metabolic stability, and boost their lipophilicity [5][6][7]. Consequently, developing new synthetic techniques that incorporate fluorine and fluorinated groups represents a significant area of research in synthetic organic chemistry [8][9]. Among the various fluorine

• ) hypervalent iodonium salts, for the efficient synthesis of fluorinated sulfoxonium ylides (Scheme 1c). Results and Discussion Since the introduction of hypervalent iodonium salts in organic chemistry, these valuable reagents have led to many new strategies for carbon–carbon bond formation [31][32]. Our

Enantioselective regiospecific addition of propargyltrichlorosilane to aldehydes catalyzed by biisoquinoline N,N’-dioxide

• Noble Brako,
• Sreerag Moorkkannur Narayanan,
• Amber Burns,
• Layla Auter,
• Valentino Cesiliano,
• Rajeev Prabhakar and
• Norito Takenaka

Beilstein J. Org. Chem. 2024, 20, 3069–3076, doi:10.3762/bjoc.20.255

• . Accordingly, the development of efficient access to optically active chiral α-allenic alcohols continues to be of significant interest in organic chemistry [11][12][13]. The asymmetric catalytic addition of allenylation reagents to aldehydes provides direct access to chiral α-allenic alcohols in an

Advances in radical peroxidation with hydroperoxides

• Oleg V. Bityukov,
• Pavel Yu. Serdyuchenko,
• Andrey S. Kirillov,
• Gennady I. Nikishin,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2024, 20, 2959–3006, doi:10.3762/bjoc.20.249

• Oleg V. Bityukov Pavel Yu. Serdyuchenko Andrey S. Kirillov Gennady I. Nikishin Vera A. Vil' Alexander O. Terent'ev N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation 10.3762/bjoc.20.249 Abstract Organic peroxides have

Synthesis of fluorinated acid-functionalized, electron-rich nickel porphyrins

• Mike Brockmann,
• Jonas Lobbel,
• Lara Unterriker and
• Rainer Herges

Beilstein J. Org. Chem. 2024, 20, 2954–2958, doi:10.3762/bjoc.20.248

• Mike Brockmann Jonas Lobbel Lara Unterriker Rainer Herges Otto Diels-Institute of Organic Chemistry, Christian-Albrechts-Universität zu Kiel, Otto-Hahn-Platz 4, 24118 Kiel, Germany 10.3762/bjoc.20.248 Abstract In this study, novel fluorinated carboxylic acid esters of the generic structure TfO

gem-Difluorovinyl and trifluorovinyl Michael acceptors in the synthesis of α,β-unsaturated fluorinated and nonfluorinated amides

• Monika Bilska-Markowska,
• Marcin Kaźmierczak,
• Wojciech Jankowski and
• Marcin Hoffmann

Beilstein J. Org. Chem. 2024, 20, 2946–2953, doi:10.3762/bjoc.20.247

• nucleophiles to unsaturated compounds with electron-withdrawing groups, is a cornerstone in constructing carbon–carbon and carbon–heteroatom bonds [1]. It is instrumental in synthesizing natural products [2][3][4][5] and pharmaceuticals [6], underlining its significance in organic chemistry. Recent

Structure and thermal stability of phosphorus-iodonium ylids

• Andrew Greener,
• Stephen P. Argent,
• Coby J. Clarke and
• Miriam L. O’Duill

Beilstein J. Org. Chem. 2024, 20, 2931–2939, doi:10.3762/bjoc.20.245

• synthetic organic chemistry, becoming indispensable tools in total synthesis, late-stage functionalisation and radiolabelling [1][2][3][4][5][6][7][8][9]. Due to their great mechanistic flexibility, including reactivity as oxidants, electrophiles, radical precursors and transmetalating agents, they often