Thiazolidinones: novel insights from microwave synthesis, computational studies, and potentially bioactive hybrids

• Luan A. Martinho,
• Victor H. J. G. Praciano,
• Guilherme D. R. Matos,
• Claudia C. Gatto and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2025, 21, 2618–2636, doi:10.3762/bjoc.21.203

• compounds [79]. The colorimetric properties of rhodanine-derived compound 3n were used in the determination of silver [80] and gold [81] metals, and as a fluorescent sensor for detection of human serum albumin (HSA) [82]. Despite this, the TZD-derived compound 4n had its photophysical properties neglected

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

• has emerged as a powerful strategy for the rapid synthesis of functionally enriched axially chiral diaryl compounds. However, due to the potential strong coordination between organoselenium compounds and transition metals, the direct construction of C–Se bonds via metal-catalyzed C–H bond

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

• of reactivity, they are environmentally sustainable alternatives to heavy metals. The advantage of hypervalent catalytic systems based on iodine lies in their reusability [63]. The oxidative contraction of the tetralone cycle 117 depended on the stoichiometric amounts of iodine(III)-based chiral

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

• include the use of transition metals or photoredox catalysts. In photoredox catalysis, radical generation often involves single-electron transfer (SET) to or from a photoexcited state of a photoredox catalyst, usually a metal complex or organic molecule. Two other notable strategies for radical generation

• -photocatalysts [10][11][12] have been successfully incorporated into enantioselective radical reactions. The use of transition metals to catalyze enantioselective radical reactions can be considered a major advancement in the field of asymmetric catalysis. Several metals such as cobalt, nickel, copper, and

• titanium have been employed successfully to catalyze enantioselective radical reactions. Two earth abundant transition metals that have found extensive application in enantioselective radical reactions are copper and nickel. These metals, particularly Ni, can be used in radical–radical coupling reactions

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

• using a wide range of noble or non-noble metal catalysts [227]. For example, treatment of levulinic acid under vapor phase in a continuous fixed-bed with bifunctional mesoporous SBA-15 doped with metals such as Nb, Ti, and Zr having hydrogenation centers and acidic sites led to VA, with GVL and alkyl

Stereoselective electrochemical intramolecular imino-pinacol reaction: a straightforward entry to enantiopure piperazines

• Margherita Gazzotti,
• Fabrizio Medici,
• Valerio Chiroli,
• Laura Raimondi,
• Sergio Rossi and
• Maurizio Benaglia

Beilstein J. Org. Chem. 2025, 21, 1897–1908, doi:10.3762/bjoc.21.147

• represent the most established approach to imino-pinacol coupling (Scheme 1), with zero-valent metals traditionally employed as reductants and various strategies extensively explored [2]. The use of alkali metals [3][4][5], as lithium and sodium, and alkaline earth metals [6], as magnesium, are

• characteristic of the earliest versions of this transformation. Several metals from the p- and the d-blocks of the periodic table, such as aluminum [7], indium [8], bismuth [7], zinc [9][10][11][12][13][14][15][16][17], and manganese [18][19], were later studied. The use of zinc, in particular, has attracted

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

• issue is a fundamentally important factor. In the present work, the reactivity of the hypophosphites of alkali metals (Li, K, Rb, and Cs) in reductive amination was explored for the first time. A set of secondary and tertiary amines was synthesized from various types of carbonyl compounds and amines

• metals other than sodium have been severely understudied in reductive transformations. While at least the structure of LiH2PO2 is known [30][31], rubidium hypophosphite is not described in the literature. There is only a very limited number of KH2PO2 utilization examples in copolymerization [32] and

• alkali metals, such as Li, K, Rb, and Cs was studied in the reductive amination for the first time. The reactivity was strongly influenced by acidity and the nature of the alkali metal cation: under neutral conditions, the yield decreased from Na to Cs, while acidic conditions with H3PO2 reversed this

Synthesis of optically active folded cyclic dimers and trimers

• Ena Kumamoto,
• Kana Ogawa,
• Kazunori Okamoto and
• Yasuhiro Morisaki

Beilstein J. Org. Chem. 2025, 21, 1603–1612, doi:10.3762/bjoc.21.124

• substituent(s) at appropriate position(s) on the benzene rings [8]. Enantiopure planar chiral [2.2]paracyclophanes have been used as chiral auxiliaries and chiral ligands for transition metals in the fields of organic and organometallic chemistry [9][10][11][12][13][14][15][16][17][18][19][20]. In 2012

Copper catalysis: a constantly evolving field

• Elena Fernández and
• Jaesook Yun

Beilstein J. Org. Chem. 2025, 21, 1477–1479, doi:10.3762/bjoc.21.109

• one of the most dynamic and versatile areas of contemporary chemical research. Once viewed primarily as a cost-effective alternative to noble metals, copper has emerged as a powerful and versatile catalyst, capable of mediating a wide array of chemical transformations through both two-electron and

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

• devoted to benzoxazoles. When applied to benzoxazole, the reaction is catalysed by transition metals such as Ag(I) [20], Mn(II) [21], Fe(III) [22][23], Co [24], Ni(II) [25] and Fe(III) [26]. However, the use of Cu(II) has increased thanks to its high tolerance towards several functional groups, high

• . Additionally, using supported metals instead of metal salts can prevent the formation of chelates, which might otherwise impact the efficiency of the procedure. Moreover, this approach can provide bifunctional catalysis as the support itself contributes to the catalyst's reactivity, thus enhancing its overall

• microwave irradiation to enhance the protocol’s efficacy. The non-thermal effects and unique ability of MW irradiation to promote reactions catalysed by solid-supported metals have already been demonstrated [53]. As shown in Scheme 1, our research is in line with earlier studies that highlight the

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

• Chemistry for Metals and Molecules, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven B-3001, Belgium 10.3762/bjoc.21.104 Abstract A one-step method has been developed for the preparation of 2,3-dihydro-2-sulfonyl-3,4,5-substituted 1,2-thiazoles by the reaction of acryl thioamides and

Oxetanes: formation, reactivity and total syntheses of natural products

• Peter Gabko,
• Martin Kalník and
• Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

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

• metals, and have been applied to a wide range of PAHs [92] and graphene nanoribbons [93]. More recently, this synthetic strategy has been independently employed by several research groups for the synthesis of non-alternant azulene-embedded PAHs. Typically, modular synthesis of direct precursors can be

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

• particularly noteworthy for its use at room temperature, requiring no transition metals, photocatalysts, or additives. Notably, Umemoto's reagent served as the trifluoromethyl source, and the reaction was facilitated under blue LED irradiation, achieving good to excellent yields. Moreover, this approach

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

• whether the connectivity has changed. The connectivity of the complex before and after optimization is compared only for bonds not involving the transition metal since the determination of bonds to transition metals is prone to errors. Instead, the geometry of the four atoms adjacent to the transition

• Pd(OAc)2 catalyst, which cannot be used since the following step relies on the Merck molecular force field (MMFF, version MMFF94s), which is not parameterized for transition metals like Pd [30][31]. If the embedding fails, the corresponding pair is removed. When a 3D geometry could be obtained, we

Gold extraction at the molecular level using α- and β-cyclodextrins

• Susana Santos Braga

Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89

• its discovery, mostly because of its glittery metallic yellow color and its ability to remain untarnished even after exposure to extremely aggressive conditions. Gold is able to keep its shine for centuries, having been deemed as the most noble of metals [1]. Present in human life since early

• because of its unique properties. Gold is soft, ductile, malleable, and a good conductor of heat and electricity, having the lowest electrochemical potential amidst metals. This means that cationic gold (in any form) can accept electrons from any reducing agent to form metallic gold while, in turn

• -OES, the precipitation ability of α-CD (0.2 mmol × 2) of a solution containing gold in the presence of palladium and platinum (33 mM KAuBr4, 33 mM K2PdBr4, and saturated K2PtBr4, at ≈26 mM), with 78.3% of the gold precipitating out of solution while for the other metals there was only precipitation of

Supramolecular assembly of hypervalent iodine macrocycles and alkali metals

• Krishna Pandey,
• Lucas X. Orton,
• Grayson Venus,
• Waseem A. Hussain,
• Toby Woods,
• Lichang Wang and
• Kyle N. Plunkett

Beilstein J. Org. Chem. 2025, 21, 1095–1103, doi:10.3762/bjoc.21.87

• Buckminster fullerene into long range assembled structures (Figure 1B) [20]. In this contribution, we explored the cation binding abilities of HIMs with first group alkali metals such as lithium and sodium. The phenylalanine-based HIM 1 used in this study was re-synthesized following the previously reported

• protocol, and the characterization data are consistent with the original dataset [18]. Through a series of crystallographic experiments, we demonstrate that HIMs coordinate with alkali metals through the periphery carbonyl oxygens via metal–oxygen bonding to form a higher order metal-coordinated

• Information File 1, Figures S6 and S7). These results suggest that there are new associative processes occurring in the presence of both LiBArF20 and NaBArF24. The NMR spectral changes observed are mainly due to the binding of metals (lithium and sodium) to HIM 1. Additionally, some of these changes could be

Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

• Betty A. Kustiana,
• Galuh Widiyarti and
• Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

• release (82). Numerous cinnamic acid derivatives with electron-withdrawing and -donating groups were converted to the corresponding amides 76–81 in moderate to excellent yields (Scheme 24B) [60]. 2.1.2 Transition-metal catalysis: Several transition metals have been exploited to catalyze O/N-acylations of

• intermediate 85 followed by reductive elimination with tertiary amine to give intermediate 86. The utilization of earth-abundant transition metals for O/N-acylation has emerged due to their low cost. For instance, Son and co-workers (2023) utilized a more cost-efficient Cu salt to access N-acyliminophosphorane

• metals, such as Yb and Ti. Salunke and co-workers (2020) utilized Yb(OTf)3 to catalyze the Boc-protection of cinnamic acid (7) via the formation of the chelate complex 101 between Boc2O and Yb(OTf)3 (Scheme 31B) [68]. Recently, Ramachandran and Alawaed (2024) reported a Ti-catalyzed direct amidation of

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

• the α-position of enamide to be an active cyclization site, with the alkyne tether acting as the nucleophile. Since it is well-established that alkynes, when activated by transition metals such as gold or platinum, can also function as electrophiles, modulating the reactivity of the decahydroquinoline

Silver(I) triflate-catalyzed post-Ugi synthesis of pyrazolodiazepines

• Muhammad Hasan,
• Anatoly A. Peshkov,
• Syed Anis Ali Shah,
• Andrey Belyaev,
• Chang-Keun Lim,
• Shunyi Wang and
• Vsevolod A. Peshkov

Beilstein J. Org. Chem. 2025, 21, 915–925, doi:10.3762/bjoc.21.74

• 13). Catalytic systems based on other transition metals including Cu(OTf)2 and the AuPPh3Cl/AgOTf combination were also tested (Table 1, entries 14 and 15). However, their performance was significantly poorer compared to AgOTf. To evaluate the scope and limitations of the optimized protocol (Table 1

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

• phosphonates and phosphine oxides using a nickel catalyst. The use of nickel complex is an important and primary factor in the C–P coupling process. Notably, the inexpensive and environmentally readily available nickel catalysis was more effective for phosphorylation than other 3D metals. Moreover, it

• exhibited higher stability compared to 4d and 5d transition metals. Through the study of a series of previous experiments, it was shown that the electron density of the nitrogen atom in the quinoline structure significantly affects the efficiency of nickel-electrocatalysis; however, other N,N- or N,O

• reaction proceeded via an oxidative addition and reductive elimination processed in the presence of Ni(0), which was produced in situ from NiBr2 in the cathode. Palladium is one of the most important metals used as a catalyst in non-electrochemical reactions. In 2020, Budnikova et al. [58] reported a

New advances in asymmetric organocatalysis II

• Radovan Šebesta

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

• 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

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

• ; hydrazones; isocyanides; Introduction Catalytic applications of non-toxic earth abundant metals like calcium are currently on the rise [1][2][3][4]. Prominent recent examples that witness the versatility of calcium catalysis include calcium-catalyzed amination of π-activated alcohols [5], the Beckmann

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

• terminus. In search of complementary approaches, other transition metals including W [9], Mo [10], Ru [11][12], Rh [13][14][15], and Ni [16][17] have been explored. Among these alternatives, Ir catalysis emerged as a particularly powerful complement to Pd catalysis. The field of iridium-catalyzed allylic

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