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

General method for the synthesis of enaminones via photocatalysis

• Paula Pérez-Ramos,
• Raquel G. Soengas and
• Humberto Rodríguez-Solla

Beilstein J. Org. Chem. 2025, 21, 1535–1543, doi:10.3762/bjoc.21.116

• ; enaminones; nickel; photocatalysis; Introduction Enaminones are relevant intermediates in organic chemistry and the pharmaceutical industry [1][2][3][4][5][6]. These enamines have a carbonyl group conjugated to a carbon–carbon double bond, owing its great versatility in organic synthesis to its ability to

• act as both electrophiles and nucleophiles [7]. This makes enaminones very reactive, providing an excellent scaffold for organic synthesis. Thus, enaminones are valuable building blocks in the preparation of several carbocyclic [8][9][10][11], heterocyclic [12][13][14][15][16][17][18] as well as

• organic chemistry. With the increasing concern on the environmental impact of organic synthesis, photocatalysis emerged as a powerful synthetic tool in organic chemistry, offering new ways to deliver diverse organic products via mild, easy to handle, and environmentally benign operations [34][35][36

Calcium waste as a catalyst in the transesterification for demanding esters: scalability perspective

• Anton N. Potorochenko and
• Konstantin S. Rodygin

Beilstein J. Org. Chem. 2025, 21, 1520–1527, doi:10.3762/bjoc.21.114

• Anton N. Potorochenko Konstantin S. Rodygin Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya nab., St. Petersburg, 199034, Russia 10.3762/bjoc.21.114 Abstract Esters are valuable compounds in fine organic synthesis and industry. The significant growth in the demand

• amounts of 1–5 wt %. Keywords: biodiesel; calcium oxide; carbide slag; ester; transesterification; Introduction The ester moiety in molecules is one of the most important functional groups, which is widespread in nature, products of fine organic synthesis, and large-scale chemical manufacturing [1][2][3

• fine organic synthesis. Results and Discussion The carbide slag was prepared by hydrolysis of commercially available calcium carbide (Sigma-Aldrich) and oven dried at 80 °C for 3 hours. The active catalyst CS600 was prepared by calcining the carbide slag at 600 °C for 2 hours. The composition of the

Ambident reactivity of enolizable 5-mercapto-1H-tetrazoles in trapping reactions with in situ-generated thiocarbonyl S-methanides derived from sterically crowded cycloaliphatic thioketones

• Grzegorz Mlostoń,
• Małgorzata Celeda,
• Marcin Palusiak,
• Heinz Heimgartner,
• Marta Denel-Bobrowska and
• Agnieszka B. Olejniczak

Beilstein J. Org. Chem. 2025, 21, 1508–1519, doi:10.3762/bjoc.21.113

• of the most important types of organic reactions with key importance for the development of methods of modern organic synthesis [1][2][3]. Therefore, conversions of 1,3-dipoles which cover not only cycloadditions but also annulation and insertion reaction attract great attention worldwide [2][3][4

Microwave-enhanced additive-free C–H amination of benzoxazoles catalysed by supported copper

• Andrei Paraschiv,
• Valentina Maruzzo,
• Filippo Pettazzi,
• Stefano Magliocco,
• Paolo Inaudi,
• Daria Brambilla,
• Gloria Berlier,
• Giancarlo Cravotto and
• Katia Martina

Beilstein J. Org. Chem. 2025, 21, 1462–1476, doi:10.3762/bjoc.21.108

• , to the best of our knowledge, this study represents one of the few examples of a heterogeneous catalysed copper-mediated C–H amination of benzoxazole. The pursuit for greener methodologies in organic synthesis and transitioning from traditional homogeneous catalysis to the use of heterogeneous

Reactions of acryl thioamides with iminoiodinanes as a one-step synthesis of N-sulfonyl-2,3-dihydro-1,2-thiazoles

• Vladimir G. Ilkin,
• Pavel S. Silaichev,
• Valeriy O. Filimonov,
• Tetyana V. Beryozkina,
• Margarita D. Likhacheva,
• Pavel A. Slepukhin,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2025, 21, 1397–1403, doi:10.3762/bjoc.21.104

• Bukireva str., Perm 614990, Russia Department of Organic & Biomolecular Chemistry, Ural Federal University, 19 Mira str., Yekaterinburg 620002, Russia Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, 22/20 S. Kovalevskoy str., Yekaterinburg 620108, Russia Sustainable

High-pressure activation for the solvent- and catalyst-free syntheses of heterocycles, pharmaceuticals and esters

• Kelsey Plasse,
• Valerie Wright,
• Guoshu Xie,
• R. Bernadett Vlocskó,
• Alexander Lazarev and
• Béla Török

Beilstein J. Org. Chem. 2025, 21, 1374–1387, doi:10.3762/bjoc.21.102

• largely gone unnoticed as an activation method for organic synthesis. A large number of applications have been reported in solid state, homogeneous and heterogeneous systems to prepare inorganic compounds and materials [7][8][9]. In contrast, high pressure organic chemistry, or HHP-initiated organic

• synthesis is still in its infancy. Despite the recent advances [10][11], the HHP applications in this field are still being developed. The first HHP-assisted organic syntheses were reported in the 1970s [12][13]. Although the mechanism of how pressure enables reactions is not fully elucidated, there is a

Recent advances in amidyl radical-mediated photocatalytic direct intermolecular hydrogen atom transfer

• Hao-Sen Wang,
• Lin Li,
• Xin Chen,
• Jian-Li Wu,
• Kai Sun,
• Xiao-Lan Chen,
• Ling-Bo Qu and
• Bing Yu

Beilstein J. Org. Chem. 2025, 21, 1306–1323, doi:10.3762/bjoc.21.100

• demonstrated a decent methodology of organic synthesis. These elegant strategies presented powerful C–H bond transformation toolkits (Figure 1b) [6][7][8]. One of the exceptions to the perfection is the pre-functionalization of substrates. Current catalytic methodologies predominantly rely on substrate

• and the relatively green chemistry of generating amidyl radicals. Amidyl radicals offer several advantages that enhance their applicability in organic synthesis: 1) The BDE of amidyl N–H bond is more than 105 kcal/mol, relative to the bond (C–H, Si–H, B–H, and Ge–H) which BDE is lower than 100 kcal

• with a systematic understanding and strategic toolkit, thereby propelling the development of direct functionalization of C–H, B–H, Si–H, and Ge–H techniques in modern organic synthesis. Most of the photocatalysts used in this review are listed in Figure 3. Review Amidyl radical from N–H bond cleavage N

Recent advances and future challenges in the bottom-up synthesis of azulene-embedded nanographenes

• Bartłomiej Pigulski

Beilstein J. Org. Chem. 2025, 21, 1272–1305, doi:10.3762/bjoc.21.99

• crucial for fine-tuning their properties. An alternative is the bottom-up approach where various nanographenes are synthesized form smaller building blocks via classical organic synthesis. This strategy enables precise control over the structure and topology, leading to the development of a vast array of

Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents

• Jiangfei Chen,
• Yi-Lin Qu,
• Ming Yuan,
• Xiang-Mei Wu,
• Heng-Pei Jiang,
• Ying Fu and
• Shengrong Guo

Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98

• been extensively investigated by researchers. Keywords: carbon radical reagents; intramolecular transformations; N-arylacrylamides; oxidative difunctionalization; radical reactions; Introduction Alkenes, as abundant and versatile feedstocks, have been widely employed in organic synthesis

Synthesis of β-ketophosphonates through aerobic copper(II)-mediated phosphorylation of enol acetates

• Alexander S. Budnikov,
• Igor B. Krylov,
• Fedor K. Monin,
• Valentina M. Merkulova,
• Alexey I. Ilovaisky,
• Liu Yan,
• Bing Yu and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2025, 21, 1192–1200, doi:10.3762/bjoc.21.96

• [1][2][3][4][5] due to the numerous applications of phosphorus-containing compounds in pharmaceuticals, biology, agrochemistry, organic synthesis, and materials science [6][7][8][9][10][11][12][13]. Among various organophosphorus compounds, β-ketophosphonates have received particular attention for

Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C–H activation with directing groups

• Julius Seumer,
• Nicolai Ree and
• Jan H. Jensen

Beilstein J. Org. Chem. 2025, 21, 1171–1182, doi:10.3762/bjoc.21.94

• Julius Seumer Nicolai Ree Jan H. Jensen Department of Chemistry, University of Copenhagen, Copenhagen, Denmark 10.3762/bjoc.21.94 Abstract The mild and selective functionalization of carbon–hydrogen (C–H) bonds remains a pivotal challenge in organic synthesis, crucial for developing complex

Biobased carbon dots as photoreductants – an investigation by using triarylsulfonium salts

• Valentina Benazzi,
• Arianna Bini,
• Ilaria Bertuol,
• Mariangela Novello,
• Federica Baldi,
• Matteo Hoch,
• Alvise Perosa and
• Stefano Protti

Beilstein J. Org. Chem. 2025, 21, 1024–1030, doi:10.3762/bjoc.21.84

• photooxidant or photoreductant in the presence of a suitable electron donor or acceptor [18], and these properties have been exploited in procedures for the formation of both C–C and C–heteroatom bonds [18][19]. Our research groups recently focused on the application of CDs in light-mediated organic synthesis

• have been considered as a promising source of aryl radicals and employed in organic synthesis [20][21][22][23][26][27][28][29][30][31][32]. This investigation aims to compare the performance of CDs prepared from several carbon precursors including citric acid, glucose, and organic waste materials via

Recent total synthesis of natural products leveraging a strategy of enamide cyclization

• Chun-Yu Mi,
• Jia-Yuan Zhai and
• Xiao-Ming Zhang

Beilstein J. Org. Chem. 2025, 21, 999–1009, doi:10.3762/bjoc.21.81

• followed by deprotection completed the total synthesis, giving rise to (−)-cephalocyclidin A in 10 steps from known compounds. Conclusion In summary, the perception of enamides as stable chemical entities with limited utilities in organic synthesis has evolved, and these compounds are now widely used in

Recent advances in controllable/divergent synthesis

• Jilei Cao,
• Leiyang Bai and
• Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

• generate cyclosiloxanes. An alternative pathway involving cleavage of another Si–O bond during the conversion from 55 to 56 and subsequently to 57 cannot be excluded. Temperature control Temperature, as a readily adjustable physical parameter in organic synthesis, offers a simple and versatile approach to

• , while the thermodynamic and kinetic properties of different reductive elimination intermediates jointly determine the switchable site selectivity. Acid–base control The strategic modulation of acid–base interactions has emerged as a powerful paradigm in organic synthesis, enabling precise control over

• radical anion, followed by cyclization and dehydration to yield bicyclic product 76. Substrate control Substrate control has emerged as a powerful strategy in organic synthesis, enabling precise manipulation of reaction pathways and stereochemical outcomes through the intrinsic structural and electronic

Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters

• Lewis McGhie,
• Hannah M. Kortman,
• Jenna Rumpf,
• Peter H. Seeberger and
• John J. Molloy

Beilstein J. Org. Chem. 2025, 21, 854–863, doi:10.3762/bjoc.21.69

• considering recent advances enabling subsequent intramolecular H-atom abstraction [51] and efficient rearrangements [73][74]. A) Energy transfer catalysis of alkenes in organic synthesis. B) Energy transfer catalysis of conjugated borylated alkenes. C) Energy transfer catalysis of simple alkenylboronic esters

Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones

• Xuhong Zhao,
• Weishuang Li,
• Mengli Yang,
• Bojie Li,
• Yaoyao Zhang,
• Lizhen Huang and
• Lei Zhu

Beilstein J. Org. Chem. 2025, 21, 839–844, doi:10.3762/bjoc.21.67

• and amino groups in III yields the target quinazolinone 3. To demonstrate the practicality of this reaction in organic synthesis, the reaction was scaled up to the gram level. For instance, the desired product 3a was obtained in 91% yield (1.45 g) when the reaction was conducted on a 10.0 mmol scale

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

• 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

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

• on the aromatic ring did not react in this system due to the incompatibility of the intermediate radicals. Electrochemical N–P bond formation Due to the importance of phosphoramidates in medicine and organic synthesis, Zhong et al. [64] reported an electrochemical P–N coupling of amines with dialkyl

• )(OR)2. The final product was formed by a simple nucleophilic substitution of the phosphorus center (Scheme 20). The N–P bond formation is a critical process in organic synthesis due to the preparation of various materials with different biological and medicinal activities. In 2021 Wang et al. [65

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

• generation of chiral secondary alkylcopper species has been a significant challenge in organic synthesis, primarily due to their inherent instability and tendency to racemization [38]. For generating the key chiral organocopper intermediates, two distinct approaches have been developed: one utilizing chiral