Visible-light-driven NHC and organophotoredox dual catalysis for the synthesis of carbonyl compounds

• Vasudevan Dhayalan

Beilstein J. Org. Chem. 2025, 21, 2584–2603, doi:10.3762/bjoc.21.200

• ]. The use of visible light as an energy source has significantly expanded the scope of organic molecule activation and its application in organic synthesis or medicinal chemistry [12], thereby driving the fast development of various photocatalytic transformations. Among these advances, dual catalysis

• carbenes (NHCs) with photocatalysts. The review encompasses transition-metal-based photocatalytic reactions for C–C and C–HA cross-coupling reactions involving various acyl fluorides, amides, aldehydes, carboxylic acids, and esters, highlighting their broad applications in organic synthesis and medicinal

• groups of MacMillan, Studer, Chi, Plunkett, Rovis, Hopkinson, and others developed NHC-involved radical reactions via visible light-promoted dual or triple photocatalysis, including NHC and transition metal-based photocatalytic reactions and their application in organic synthesis [41][42][43][44][45][46

Total syntheses of highly oxidative Ryania diterpenoids facilitated by innovations in synthetic strategies

• Zhi-Qi Cao,
• Jin-Bao Qiao and
• Yu-Ming Zhao

Beilstein J. Org. Chem. 2025, 21, 2553–2570, doi:10.3762/bjoc.21.198

• primary driving forces behind the advancement of organic synthetic chemistry. With rapidly evolving organic synthesis technologies, a diverse array of novel methods and sophisticated strategies continues to emerge. These approaches not only complement and synergize with one another but also significantly

• diterpenoids; synthetic strategy; total synthesis; Introduction Organic synthesis, as a cornerstone of chemical research, is dedicated to constructing complex natural products or target molecules from simple and readily available starting materials via a series of precise and efficient chemical reactions

Isoorotamide-based peptide nucleic acid nucleobases with extended linkers aimed at distal base recognition of adenosine in double helical RNA

• Grant D. Walby,
• Brandon R. Tessier,
• Tristan L. Mabee,
• Jennah M. Hoke,
• Hallie M. Bleam,
• Angelina Giglio-Tos,
• Emily E. Harding,
• Vladislavs Baskevics,
• Martins Katkevics,
• Eriks Rozners and
• James A. MacKay

Beilstein J. Org. Chem. 2025, 21, 2513–2523, doi:10.3762/bjoc.21.193

• Department of Chemistry, Ohio Wesleyan University, Delaware, OH, 43015, USA Department of Chemistry, Binghamton University, 4400 Vestal Parkway East, Binghamton, NY 13902, USA Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, LV-1006, Latvia 10.3762/bjoc.21.193 Abstract Non-coding ribonucleic

Assembly strategy for thieno[3,2-b]thiophenes via a disulfide intermediate derived from 3-nitrothiophene-2,5-dicarboxylate

• Roman A. Irgashev

Beilstein J. Org. Chem. 2025, 21, 2489–2497, doi:10.3762/bjoc.21.191

• Roman A. Irgashev Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Ekaterinburg, 620137, Russia 10.3762/bjoc.21.191 Abstract A versatile synthetic route to thieno[3,2-b]thiophenes was elaborated from dimethyl 3-nitrothiophene-2,5-dicarboxylate

• organic synthesis. A widely adopted strategy for building the TT scaffold involves the annulation of a second thiophene ring onto a suitably functionalized thiophene precursor. Most commonly, this approach starts from halogenated thiophenes such as 3-bromo- or 3-chlorothiophenes, which undergo subsequent

• Analytical studies were carried out using equipment of the Center for Joint Use «Spectroscopy and Analysis of Organic Compounds» at the Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences. Funding This study was supported by the Russian Science Foundation, Grant No

Palladium-catalyzed regioselective C1-selective nitration of carbazoles

• Vikash Kumar,
• Jyothis Dharaniyedath,
• Aiswarya T P,
• Sk Ariyan,
• Chitrothu Venkatesh and
• Parthasarathy Gandeepan

Beilstein J. Org. Chem. 2025, 21, 2479–2488, doi:10.3762/bjoc.21.190

• strategies in streamlining access to nitro-functionalized carbazoles for applications in organic synthesis and materials science. Experimental A 15 mL pressure tube was charged with Pd2(dba)3 (18.3 mg, 0.02 mmol, 10 mol %), N-(pyridin-2-yl)-9H-carbazole 1 (0.2 mmol, 1.0 equiv), and AgNO3 (41 mg, 0.24 mmol

Ex-situ generation of gaseous nitriles in two-chamber glassware for facile haloacetimidate synthesis

• Nikolai B. Akselvoll,
• Jonas T. Larsen and
• Christian M. Pedersen

Beilstein J. Org. Chem. 2025, 21, 2465–2469, doi:10.3762/bjoc.21.188

• danger of working with this toxic gas, restricts its use in laboratory scale synthesis. Consequently, when used in organic synthesis, trifluoroacetonitrile is typically synthesized on demand. The most common method is by dehydration of trifluoroacetamide using Gilman’s method with phosphorous pentoxide

Catalytic enantioselective synthesis of selenium-containing atropisomers via C–Se bond formations

• Qi-Sen Gao,
• Zheng-Wei Wei and
• Zhi-Min Chen

Beilstein J. Org. Chem. 2025, 21, 2447–2455, doi:10.3762/bjoc.21.186

• many applications in industry, but also plays an important role in many fields, such as electronics [3], agriculture [4], environmental protection [5] and cosmetics [6]. Chiral organic selenium-containing compounds also have important applications in organic synthesis and biomedicine [7][8]. These

Transformation of the cyclohexane ring to the cyclopentane fragment of biologically active compounds

• Natalya Akhmetdinova,
• Ilgiz Biktagirov and
• Liliya Kh. Faizullina

Beilstein J. Org. Chem. 2025, 21, 2416–2446, doi:10.3762/bjoc.21.185

• -dihydronaphthalenes. Silva et al. have also developed an effective method for the stereoselective oxidation of tetralone derivatives using chiral hypervalent iodine reagents [61][62]. Hypervalent iodine compounds are widely used in organic synthesis as selective oxidants and enantiomerically pure reagents. In terms

The high potential of methyl laurate as a recyclable competitor to conventional toxic solvents in [3 + 2] cycloaddition reactions

• Ayhan Yıldırım and
• Mustafa Göker

Beilstein J. Org. Chem. 2025, 21, 2389–2415, doi:10.3762/bjoc.21.184

• different sources [4][5]. In order to fulfil this requirement, a considerable number of green solvents of various classes have been developed for a range of applications, including the extraction of natural compounds [6][7][8][9], food analysis [10][11][12], pharmacology [13][14][15], and organic synthesis

Enantioselective radical chemistry: a bright future ahead

• Anna C. Renner,
• Sagar S. Thorat,
• Hariharaputhiran Subramanian and
• Mukund P. Sibi

Beilstein J. Org. Chem. 2025, 21, 2283–2296, doi:10.3762/bjoc.21.174

• powerful tool in organic synthesis [65][66][67][68][69][70]. Over the years, many catalytic systems were developed by merging photoredox processes and other catalytic modes. Some of the disadvantages of chiral Lewis acid catalysis such as toxic reducing agents, high catalytic loading, and limitations in

• selective synthesis owing to their unprecedented catalytic activity and selectivity. Advances in the field of protein engineering have made enzymatic catalysis more amenable to enantioselective organic synthesis in the past decade. Recent advances in the development of synergistic catalytic systems

• bengal), affording diversely substituted products [78]. Electrochemical radical reactions The organic chemistry community has witnessed a resurgence of interest in electrochemical methods for organic synthesis [79]. Organic electrochemistry can provide mild reaction conditions, good functional group

Pathway economy in cyclization of 1,n-enynes

• Hezhen Han,
• Wenjie Mao,
• Bin Lin,
• Maosheng Cheng,
• Lu Yang and
• Yongxiang Liu

Beilstein J. Org. Chem. 2025, 21, 2260–2282, doi:10.3762/bjoc.21.173

• rapid molecular diversification, offering transformative potential for green chemistry and pharmaceutical applications. By unifying mechanistic insights with practical synthetic design, this review provides valuable guidance for future innovations in precision organic synthesis. Keywords: economical

• synthesis; 1,n-enynes; pathway economy; small-molecule skeletons; Introduction As organic synthesis concepts continue to evolve, economical synthesis remains a foundational principle for synthetic chemists [1][2][3][4][5][6][7]. The essence of economical synthesis lies in the conservation of materials and

• importance of reducing the time required for reaction processes and conducting multistep reactions within a single pot (Scheme 1a) [6][7]. Contemporary organic synthesis is progressively approaching ideal synthesis – achieving highly functionalized target molecular frameworks in a single step. This paradigm

Electrochemical cyclization of alkynes to construct five-membered nitrogen-heterocyclic rings

• Lifen Peng,
• Ting Wang,
• Zhiwen Yuan,
• Bin Li,
• Zilong Tang,
• Xirong Liu,
• Hui Li,
• Guofang Jiang,
• Chunling Zeng,
• Henry N. C. Wong and
• Xiao-Shui Peng

Beilstein J. Org. Chem. 2025, 21, 2173–2201, doi:10.3762/bjoc.21.166

• of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China 10.3762/bjoc.21.166 Abstract Organic five-membered rings have shown significant applications in the fields of organic synthesis, natural products, organic materials and pharmaceuticals for their unique

• organic synthesis [1][2][3][4][5][6][7][8][9][10][11][12][13][14] but also are critical moieties in natural products [15][16][17][18], organic materials [19] and pharmaceuticals [20][21][22][23][24] due to their unique chemical, electrical, optical, pharmacological and biological properties. Gracilioether

• search tools and profiles applied. Review Construction of indoles Indoles, exhibiting interesting photoelectric properties and biological activities, were widely applied in organic synthesis, pharmacology and organic materials science [112][113][114][115][116][117][118][119][120][121][122][123][124][125

C2 to C6 biobased carbonyl platforms for fine chemistry

• Jingjing Jiang,
• Muhammad Noman Haider Tariq,
• Florence Popowycz,
• Yanlong Gu and
• Yves Queneau

Beilstein J. Org. Chem. 2025, 21, 2103–2172, doi:10.3762/bjoc.21.165

• of Science and Technology, 1037 Luoyu road, Wuhan 430074, China 10.3762/bjoc.21.165 Abstract The carbonyl group is central in organic synthesis, thanks to its ability to undergo a vast range of different chemical transformations on its carbon center or at the neighboring positions. Due to the high

• organic synthesis. Therefore, synthetic chemists can base strategies on the existing reactivity of carbonyl compounds for defining novel routes converting biobased platform molecules containing carbonyl groups to prepare fine organic chemicals [21][22]. Following this approach, researchers can obtain

• toward useful biobased functional compounds or intermediates with applications in fuels, polymer chemistry and fine organic synthesis (CH activation, Piancatelli rearrangement, etc.). Conversion of furfural to alcohols, aldehydes and ketones: One of the most important transformations of furfural is its

Solar thermal fuels: azobenzene as a cyclic photon–heat transduction platform

• Jie Yan,
• Shaodong Sun,
• Minghao Wang and
• Si Wu

Beilstein J. Org. Chem. 2025, 21, 2036–2047, doi:10.3762/bjoc.21.159

• ]. Since Olmsted’s pioneering exploration of azobenzene compounds as solar thermal fuels in 1983 [42], significant breakthroughs have been achieved through interdisciplinary integration of organic synthesis, functional materials engineering, photophysical mechanism analysis, and computational chemistry. So

α-Ketoglutaric acid in Ugi reactions and Ugi/aza-Wittig tandem reactions

• Vladyslav O. Honcharov,
• Yana I. Sakhno,
• Olena H. Shvets,
• Vyacheslav E. Saraev,
• Svitlana V. Shishkina,
• Tetyana V. Shcherbakova and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2021–2029, doi:10.3762/bjoc.21.157

• quinoxalinones and Ugi reaction products may be valuable for organic synthesis and medicinal chemistry because the presence of a free carboxyl group makes them promising for use as building blocks for the construction of complex heterocyclic structures, including those using multicomponent reactions. Some

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

• Leticia A. Gomes and
• Steven A. Lopez

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

Measuring the stereogenic remoteness in non-central chirality: a stereocontrol connectivity index for asymmetric reactions

• Ivan Keng Wee On,
• Yu Kun Choo,
• Sambhav Baid and
• Ye Zhu

Beilstein J. Org. Chem. 2025, 21, 1995–2006, doi:10.3762/bjoc.21.155

• chiral molecules. Keywords: asymmetric reactions; axial chirality; catalysis; planar chirality; stereocontrol; Introduction Chirality is a ubiquitous and fundamental phenomenon in nature and thus holds an irreplaceable position in organic synthesis. At its most rudimental definition, chirality in a

Aryl iodane-induced cascade arylation–1,2-silyl shift–heterocyclization of propargylsilanes under copper catalysis

• Rasma Kroņkalne,
• Rūdolfs Beļaunieks,
• Armands Sebris,
• Anatoly Mishnev and
• Māris Turks

Beilstein J. Org. Chem. 2025, 21, 1984–1994, doi:10.3762/bjoc.21.154

• Rasma Kronkalne Rudolfs Belaunieks Armands Sebris Anatoly Mishnev Maris Turks Institute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena str. 3, LV-1048, Riga, Latvia Latvian Institute of Organic Synthesis, Aizkraukles str. 21

Photochemical reduction of acylimidazolium salts

• Michael Jakob,
• Nick Bechler,
• Hassan Abdelwahab,
• Fabian Weber,
• Janos Wasternack,
• Leonardo Kleebauer,
• Jan P. Götze and
• Matthew N. Hopkinson

Beilstein J. Org. Chem. 2025, 21, 1973–1983, doi:10.3762/bjoc.21.153

• carboxylic acid derivatives involving hydrogen-atom transfer have not been reported despite the fundamental importance of carbonyl reduction processes in organic synthesis [46]. Here, we report the results of our investigation into such reactions using an acylazolium salt derived from benzoic acid as a model

• . Given the importance of carboxyl reduction reactions in organic synthesis and the recent explosion in interest in light-mediated NHC-catalyzed coupling reactions, we believe this work will be of value to the community and further studies on these systems, including on the development of catalytic

• yield (Scheme 3c). The successful generation of the aldehyde from the azolium species derived from the corresponding carboxylic acid highlights the potential of this two-step sequence as a method for the partial reduction of carboxyl compounds. Such transformations can be challenging in organic

Fe-catalyzed efficient synthesis of 2,4- and 4-substituted quinolines via C(sp²)–C(sp²) bond scission of styrenes

• Prafull A. Jagtap,
• Manish M. Petkar,
• Vaishnavi R. Sawant and
• Bhalchandra M. Bhanage

Beilstein J. Org. Chem. 2025, 21, 1799–1807, doi:10.3762/bjoc.21.142

• probes for sensing and bioimaging applications (Figure 1) [16][17]. Quinoline-derived metal complexes have also demonstrated broad utility, functioning as effective catalysts in organic synthesis and finding applications across medicinal chemistry, materials science, photovoltaics, and chemical sensing

• production of approximately 30 million tons annually [40]. Their low cost and widespread availability make them highly valuable as fundamental building blocks in organic synthesis. Over the past few decades, the direct functionalization of styrenes has emerged as a prominent research area due to its

• -metal catalysts. One of the key transformations in organic synthesis is the selective oxidative cleavage of alkenes to yield ketones or aldehydes [43][44][45][46][47]. Traditionally, such transformations have been achieved using various oxidizing agents, transition-metal-based systems, organo- and

Preparation of a furfural-derived enantioenriched vinyloxazoline building block and exploring its reactivity

• Madara Darzina,
• Anna Lielpetere and
• Aigars Jirgensons

Beilstein J. Org. Chem. 2025, 21, 1737–1741, doi:10.3762/bjoc.21.136

• Madara Darzina Anna Lielpetere Aigars Jirgensons Latvian Institute of Organic Synthesis Aizkraukles 21, Riga, LV-1006, Latvia Faculty of Natural Sciences and Technology, Riga Technical University, 3 P. Valdena Street, Riga LV-1048, Latvia 10.3762/bjoc.21.136 Abstract N-Alloc-protected furfuryl

Influence of the cation in hypophosphite-mediated catalyst-free reductive amination

• Natalia Lebedeva,
• Fedor Kliuev,
• Olesya Zvereva,
• Klim Biriukov,
• Evgeniya Podyacheva,
• Maria Godovikova,
• Oleg I. Afanasyev and
• Denis Chusov

Beilstein J. Org. Chem. 2025, 21, 1661–1670, doi:10.3762/bjoc.21.130

• Scientific) and readily available in bulk quantities compound. In organic synthesis, it is most commonly used in metal-catalyzed reductions where NaH2PO2 serves as a molecular hydrogen donor [6][7][8][9][10][11][12][13][14][15][16]. However, recent studies demonstrated application of hypophosphites as a

Catalytic asymmetric reactions of isocyanides for constructing non-central chirality

• Jia-Yu Liao

Beilstein J. Org. Chem. 2025, 21, 1648–1660, doi:10.3762/bjoc.21.129

• become a hot topic in synthetic organic chemistry. Isocyanides (also termed isonitriles) are a class of highly versatile building blocks in organic synthesis, participating in a wide range of transformations including multicomponent reactions (e.g., the well-known Passerini and Ugi reactions) [13][14][15

• transformations of isocyanides for generating architectures bearing axial, planar, helical, and inherent chirality. These advances not only offer efficient routes to enantioenriched non-central chiral compounds but also significantly broaden the utility of isocyanides in organic synthesis. Nevertheless, despite

Photocatalysis and photochemistry in organic synthesis

• Timothy Noël and
• Bartholomäus Pieber

Beilstein J. Org. Chem. 2025, 21, 1645–1647, doi:10.3762/bjoc.21.128

• impact of [Ru(bpy)3]Cl2 on several research areas, including solar energy conversion [5], optosensing [6], photodynamic therapy [7][8] and bioimaging [9]. Scattered examples of [Ru(bpy)3]Cl2 being used as a photocatalyst for visible-light-driven organic synthesis appeared in the scientific literature as

• implement. Two decades later, photocatalysis and photochemistry remain among the most studied topics in modern organic synthesis. Nowadays, chemists can choose from a wide range of organometallic [12][13], organic [14][15], or heterogeneous photocatalysts [16][17] to trigger visible-light photoredox

• thematic issue that visible light increases the reaction rate of palladium-catalyzed Negishi cross-couplings [34]. The integration of enabling technologies has also contributed to the success of photocatalytic organic synthesis [35]. Automated reaction platforms, high-throughput experimentation techniques

3-Aryl-2H-azirines as annulation reagents in the Ni(II)-catalyzed synthesis of 1H-benzo[4,5]thieno[3,2-b]pyrroles

• Julia I. Pavlenko,
• Pavel A. Sakharov,
• Anastasiya V. Agafonova,
• Derenik A. Isadzhanyan,
• Alexander F. Khlebnikov and
• Mikhail S. Novikov

Beilstein J. Org. Chem. 2025, 21, 1595–1602, doi:10.3762/bjoc.21.123

• reaction, in which 2H-azirines act as the annulation reagent. Keywords: annulation; azirines; benzothiophenes; indoles; nickel catalysis; Introduction 2H-Azirines represent a valuable class of nitrogen heterocycles that are widely used as versatile building blocks in organic synthesis. In particular, the