Synthesis of diaryl phosphates using phytic acid as a phosphorus source

• Kazuya Asao,
• Seika Matsumoto,
• Haruka Mori,
• Riku Yoshimura,
• Takeshi Sasaki,
• Naoya Hirata,
• Yasuyuki Hayakawa and
• Shin-ichi Kawaguchi

Beilstein J. Org. Chem. 2026, 22, 213–223, doi:10.3762/bjoc.22.15

• soil. It can potentially serve as a phosphorus source in the syntheses of organic phosphates; however, this approach has not been utilized for the preparation of phosphate esters. In this study, we report the first successful synthesis of phosphate esters using phytic acid as a phosphorus source. Crude

• esterification with alcohols using sustainable biomass-derived phytic acid as a phosphorus source (Figure 2E). This approach can facilitate the development of environmentally friendly phosphate ester production as well as phosphorus recovery and recycling techniques. To date, the preparation of phosphate esters

• A total P analysis was performed according to a test method for industrial wastewater standardized in the Japanese Industrial Standards (JIS K 0102 46.3). Step 1 (preparation of a coloring agent): Hexaammonium heptamolybdate tetrahydrate (300 mg) and antimony potassium tartrate trihydrate (12 mg

Screwing the helical chirality through terminal peri-functionalization

• Devesh Chandra,
• Sachin and
• Upendra Sharma

Beilstein J. Org. Chem. 2026, 22, 205–212, doi:10.3762/bjoc.22.14

• -functionalization, where a bulkier handle provides the required enantiomerization barrier to screw helical chirality (Figure 1C and D). A straight forward preparation of various carbohelicenes via an organocatalytic enantioselective hydroamination reaction of polyaromatic phenols with diazodicarboxamide derivatives

Base-promoted deacylation of 2-acetyl-2,5-dihydrothiophenes and their oxygen-mediated hydroxylation

• Vladimir G. Ilkin,
• Margarita Likhacheva,
• Igor V. Trushkov,
• Tetyana V. Beryozkina,
• Vera S. Berseneva,
• Vladimir T. Abaev,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2026, 22, 192–204, doi:10.3762/bjoc.22.13

• convenient tool for the preparation of phenols from aromatic ketones, several specific approaches have been developed for the synthesis of hydroxylated heterocycles [30][31][32][33][34]. The deacylation of ketones is also another important direction of their transformation [35][36][37][38]. Dihydrothiophenes

Improved synthesis and physicochemical characterization of the selective serotonin 2A receptor agonist 25CN-NBOH

• Adrian G. Rossebø,
• Hannah G. Kolberg,
• Anders E. Tønder,
• Louise Kjaerulff,
• Poul Erik Hansen,
• Karla A. Frydenvang,
• Jesper Østergaard and
• Jesper L. Kristensen

Beilstein J. Org. Chem. 2026, 22, 175–184, doi:10.3762/bjoc.22.11

• ) and water at 25 ± 0.5 °C. The solutions comprising 0.2 mg/mL of 1·HCl were kept in a temperature-controlled incubator, and samples were measured by HPLC immediately after sample preparation as well as after one and four weeks for the experiments in phosphate buffer and after four weeks for experiments

A new synthesis of Tyrian purple (6,6’-dibromoindigo) and its corresponding sulfonate salts

• Holly Helmers,
• Mark Horton,
• Julie Concepcion,
• Jeffrey Bjorklund and
• Nicholas C. Boaz

Beilstein J. Org. Chem. 2026, 22, 167–174, doi:10.3762/bjoc.22.10

• at different pH values. A) Generalized synthetic scheme for several previous syntheses of 6,6’-dibromoindigo. B) The synthetic scheme for 6,6’-dibromoindigo described in this work. Synthetic scheme for the preparation of 6,6’-dibromoindigo from p-bromotoluene (5). Nitration of p-bromotoluene (5

Circumventing Mukaiyama oxidation: selective S–O bond formation via sulfenamide–alcohol coupling

• Guoling Huang,
• Huarui Zhu,
• Shuting Zhou,
• Wanlin Zheng,
• Fangpeng Liang,
• Zhibo Zhao,
• Yifei Chen and
• Xunbo Lu

Beilstein J. Org. Chem. 2026, 22, 158–166, doi:10.3762/bjoc.22.9

• preparation of sulfinimidate esters remain scarce. For instance, Degennaro and Luisi reported a direct amination strategy using N,N’-disubstituted sulfenamides in alcoholic solvents; however, this method suffered from limited substrate scope [13]. Subsequently, Malacria and co-workers reported an oxidative

Design and synthesis of an axially chiral platinum(II) complex and its CPL properties in PMMA matrix

• Daiki Tauchi,
• Sota Ogura,
• Misa Sakura,
• Kazunori Tsubaki and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2026, 22, 143–150, doi:10.3762/bjoc.22.7

• reaction of S/R-1 with trimethtylsilylacetylene in toluene (Scheme 1). Subsequent deprotection of the trimethylsilyl (TMS) groups with tetrabutylammonium fluoride (TBAF) afforded the desired ligand S/R-3. The preparation of the target platinum(II) complex was performed by using a similar procedure of other

Total synthesis of natural products based on hydrogenation of aromatic rings

• Haoxiang Wu and
• Xiangbing Qi

Beilstein J. Org. Chem. 2026, 22, 88–122, doi:10.3762/bjoc.22.4

• 18, 20 to piperidine compounds using [CpRhCl2]2 as a metal catalyst and formic acid as a hydrogen source (Scheme 3) [45]. Different with other previous studies, this method allows for substituents at the 3-position of pyridine, enabling the rapid preparation of chiral piperidine compounds. It should

• hydrogenation feasible, it also increased the complexity of the synthetic route, limiting its suitability for large-scale preparation of 157. Consequently, the authors redirected their efforts toward homogeneous catalytic hydrogenation, a field that has seen rapid progress in recent years. Upon converting 161

Advances in Zr-mediated radical transformations and applications to total synthesis

• Hiroshige Ogawa and
• Hugh Nakamura

Beilstein J. Org. Chem. 2026, 22, 71–87, doi:10.3762/bjoc.22.3

• A (72). Notably, this strategy enabled the preparation of tetratryptomycin A (72) on a multigram scale, providing a total of 21 g of tetratryptomycin A (72). The synthesized tetratryptomycin A (72) was then employed in the total synthesis of cyctetryptomycins (76 and 77). Under chemical oxidation

Synthesis and applications of alkenyl chlorides (vinyl chlorides): a review

• Daniel S. Müller

Beilstein J. Org. Chem. 2026, 22, 1–63, doi:10.3762/bjoc.22.1

• Synthesis of Acetylenes” [29] which discusses the preparation of alkenyl chlorides via ketone chlorination using PCl5 (Figure 3A). The synthesis of β-chlorovinyl ketones was later reviewed by Poland and Benson in 1966 (Figure 3B) [30]. More recently, Morandi and co-workers summarized transition-metal

• – including iodides, bromides, and chlorides – this review is limited to studies that report at least two distinct examples of alkenyl chloride formation. The preparation of 1,1-dichloroalkenes has been comprehensively reviewed by Chelucci and will not be revisited here [44]. Conversely, 1,2-dichloroalkene

• HIV-1 non-nucleoside reverse transcriptase inhibitor, they aimed to improve the preparation of compound 19, whose yield had previously been limited to 22% following a similar route. They noticed that in situ-generated species such as POCl3 or HCl triggered ring opening of dichloride 15 to produce a

One-pot synthesis of ethylmaltol from maltol

• Immanuel Plangger,
• Marcel Jenny,
• Gregor Plangger and
• Thomas Magauer

Beilstein J. Org. Chem. 2025, 21, 2755–2760, doi:10.3762/bjoc.21.212

• helpful discussions during the preparation of this manuscript. Furthermore, we are thankful to Christoph Kreutz (University of Innsbruck) and Thomas Müller (University of Innsbruck) for support with NMR and HRMS studies. Funding T.M. acknowledges the Austrian Academy of Sciences (OeAW) and the Center for

Sustainable electrochemical synthesis of aliphatic nitro-NNO-azoxy compounds employing ammonium dinitramide and their in vitro evaluation as potential nitric oxide donors and fungicides

• Alexander S. Budnikov,
• Nikita E. Leonov,
• Michael S. Klenov,
• Andrey A. Kulikov,
• Igor B. Krylov,
• Timofey A. Kudryashev,
• Aleksandr M. Churakov,
• Alexander O. Terent’ev and
• Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2025, 21, 2739–2754, doi:10.3762/bjoc.21.211

• approaches focus mainly on intramolecular radical cyclizations [42][54][55][56][57][58][59][60][61][62][63], while intermolecular [1][64][65][66][67][68] N–N coupling remains a poorly studied area. In addition to the preparation of azo compounds [69][70], intermolecular N–N coupling reactions are of

• leaving group X. The second step is substitutive nitration of the latter with nitronium salts (NO2BF4, (NO2)2SiF6) or N2O5). The main limitations of this approach are the use of hazardous and expensive nitrating reagents and its inapplicability for preparation of nitro-NNO-azoxy compounds containing

• single step. The synthesized products demonstrated marked in vitro NO-donor ability and fungicidal activity against a broad range of phytopathogenic fungi. Experimental Although we have encountered no difficulties during preparation and handling of compounds described and used in this paper, they are

Recent advancements in the synthesis of Veratrum alkaloids

• Morwenna Mögel,
• David Berger and
• Philipp Heretsch

Beilstein J. Org. Chem. 2025, 21, 2657–2693, doi:10.3762/bjoc.21.206

• the C4/C9 oxo bridge installed (see Scheme 31). Notably, the asymmetric preparation of 100 has also been described (9 steps LLS from commercial substances) [50][51]. The introduction of C7–OH and reduction of double bonds was achieved following a nine-step sequence of redox manipulations to arrive at

• interconversions were employed to install the propargyl bromide moiety and conclude the synthesis of diyne fragment 112 containing the A,B-rings. The preparation of alkyne fragment 116 started with an Evans syn-aldol reaction between propionic acid Evans auxiliary 113 and aldehyde 114 (prepared in two steps from δ

Chemoenzymatic synthesis of the cardenolide rhodexin A and its aglycone sarmentogenin

• Fuzhen Song,
• Mengmeng Zheng,
• Dongkai Wang,
• Xudong Qu and
• Qianghui Zhou

Beilstein J. Org. Chem. 2025, 21, 2637–2644, doi:10.3762/bjoc.21.204

• only causes damage to the environment, but also greatly restricts further research for their pharmaceutical applications. Therefore, substantial synthetic efforts have been devoted towards the preparation of these valuable targets recently [8][9][10][11][12][13][14][15][16][17]. Rhodexin A was firstly

Efficient solid-phase synthesis and structural characterization of segetalins A–H, J and K

• Liangyu Liu,
• Wanqiu Lu,
• Quanping Guo and
• Zhaoqing Xu

Beilstein J. Org. Chem. 2025, 21, 2612–2617, doi:10.3762/bjoc.21.202

• against Gram-positive bacteria), will be conducted in our laboratory. Cyclization reactions to segetalins A–H, J and K. The CD spectra of segetalins A–H, J and K. Preparation of segetalins A–H, J and K. Preparation of linear peptides for segetalins A–H, J and K. Supporting Information Supporting

Silica gel with covalently attached bambusuril macrocycle for dicyanoaurate sorption from water

• Michaela Šusterová and
• Vladimír Šindelář

Beilstein J. Org. Chem. 2025, 21, 2604–2611, doi:10.3762/bjoc.21.201

• remains a major challenge due to the strong hydration of anions. Here, we report the preparation of silica gel functionalized with covalently anchored bambusuril macrocycles. In aqueous solution, this material efficiently sorbs dicyanoaurate(I), the key anion in gold mining, even in the presence of

• carried out in nitrogen atmosphere. The dicyanoaurate concentration in solution was determined according to UV–vis spectra recorded with a CARY 60 spectrophotometer (Agilent Technologies). NMR spectra were recorded on a Bruker Avance III 300 spectrometer (300.15 Hz, 298.15 K). Preparation of SG-NHCO-BU1

• was filtered and thoroughly washed with DMF, water and methanol in order to remove byproducts and unreacted BU1. After air-drying, SG-NHCO-BU1 was obtained. Preparation of SG-BU1 For the preparation of SG-BU1 with electrostatically bound BU1 on the surface of silica gel, a-SG (0.9 g) was suspended in

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

• , particularly the synergistic combination of N-heterocyclic carbenes (NHCs) with organic photocatalysts, has opened new avenues in molecular construction, particularly for the novel, practical preparation of carbonyl group-containing compounds [13][14][15][16]. These ubiquitous ketone, ester, and amide

• , and advanced optical and energy materials. Review Visible-light-driven NHC/4CzIPN-catalyzed reactions Recently, Shu and co-workers developed a direct and innovative preparation of highly functionalized aryl amide derivatives 3 from aryl aldehydes 1 and substituted imines 2 under mild conditions in the

• existing metal-catalyzed C–H bond functionalization methods (Scheme 3) [53]. Recently, Scheidt et al. discovered an NHC/organic photoredox-catalyzed three-component coupling reaction for the efficient and novel preparation of γ-aryloxy ketone scaffolds 12. This transformation builds on the emerging field

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

• polyhydroxylated molecular framework has posed a significant synthetic challenge, impeding the preparation of derivatives for SAR exploration. In 2017, the Reisman group addressed this issue by drawing upon an analysis of Deslongchamps’s prior synthetic work [45] (Scheme 8). They hypothesized that utilizing an

• ). The synthesis commenced with the preparation of key cyclization precursor 98 via Barbier coupling and Babler–Dauben oxidative rearrangement. A pivotal palladium-catalyzed Heck/carbonylative cyclization then efficiently furnished the ABC tricyclic core 99. Notably, adding N-formylsaccharin under a CO

Ni-promoted reductive cyclization cascade enables a total synthesis of (+)-aglacin B

• Si-Chen Yao,
• Jing-Si Cao,
• Jian Xiao,
• Ya-Wen Wang and
• Yu Peng

Beilstein J. Org. Chem. 2025, 21, 2548–2552, doi:10.3762/bjoc.21.197

• 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TBCD) in CH2Cl2 followed by reaction with allyl alcohol, provided β-bromo acetal 5 in 30% overall yield starting from alcohol 6. With a successful preparation of the cyclization precursor 5, the designed nickel-promoted reductive tandem cyclization was pursued

Pentacyclic aromatic heterocycles from Pd-catalyzed annulation of 1,5-diaryl-1,2,3-triazoles

• Kaylen D. Lathrum,
• Emily M. Hanneken,
• Katelyn R. Grzelak and
• James T. Fletcher

Beilstein J. Org. Chem. 2025, 21, 2524–2534, doi:10.3762/bjoc.21.194

• modification of the base-catalyzed conditions reported by Kwok [53], where a stoichiometric plus additional catalytic amount of tetraethylammonium hydroxide base in DMSO solvent was used to promote tandem trimethylsilyl deprotection and cycloaddition in one preparation (Figure 3). Isolated yields of this

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

• . Nucleophilic substitution of the nitro group with sulfur nucleophiles, including thioacetate or disulfide anions as well as thioacetamide, yielded bis(thiophen-3-yl)disulfide and sulfide derivatives. The disulfide served as a suitable precursor for the preparation of 3-alkylthio-substituted thiophene-2,5

• cyclization to furnish the TT framework [2][23][24]. Despite the wide structural diversity of TT derivatives, 3-hydroxy-substituted analogues remain rare, with only a few synthetic strategies described for their preparation, as illustrated in Scheme 1. One such route involves sulfur insertion into a thiophen

• tolerated both electron-donating and electron-withdrawing groups on the aromatic ring, and the yields for this series ranged from 76% to 92%. Piperonyl mesylate was successfully used in the synthesis of compound 4g (92% yield), while thiophene-2-ylmethyl mesylate was used for the preparation of compound 4h

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 LG and 1,3-butadiene (Scheme 3). The ratio of the resulting regioisomers was 5:3 in favor of the 5-methoxycarbonyl derivative 17a. The synthesized cyclopentane derivatives 17a,b, 18, and 19 may be useful for the preparation of iridoids and other biologically active cyclopentanoids. An alternative

• with MeONa or t-BuOK as base led to the formation of diol 29 with a yield of 40%, which is interesting for the synthesis of angeloside (31) [23]. An alternative preparation of diol 29 involved ozonolysis of the double bond in dioxolane 26 at −78 °C in methanol, followed by reduction of the ozonide with

• unprecedentedly highly oxygenated five-membered D-ring. These compounds exhibit potent anti-inflammatory and analgesic activity both in vitro and in vivo [44]. The synthetic method for the preparation of dactylicapnosines A (63) and B (64) was based on the known phenol 65 and involved the ring contraction of p

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

• consisting of a combination of isoxazolidine rings [36][37][38][39][40][41]. It has been demonstrated that such cycloaddition reactions are also employed in the efficient preparation of biologically active molecules, including nucleosides, β-lactam class antibiotics, peptides, and amino acids, as well as

• for the preparation of such cyclic compounds and/or their fused cyclic systems typically necessitate the use of toxic solvents, including chloroform, benzene, toluene etc. [32][53][54][55][56][57][58][59]. Indeed, the selection of conventional organic solvents, including benzene, toluene and

• -based nitrone with some maleimides via a mechanochemical route in a solvent-free medium [67][68]. The development of environmentally friendly green methodologies for the preparation of heterocyclic compounds via such cycloaddition reactions is a significant and ongoing research area that should not be

An Fe(II)-catalyzed synthesis of spiro[indoline-3,2'-pyrrolidine] derivatives

• Elizaveta V. Gradova,
• Nikita A. Ozhegov,
• Roman O. Shcherbakov,
• Alexander G. Tkachenko,
• Larisa Y. Nesterova,
• Elena Y. Mendogralo and
• Maxim G. Uchuskin

Beilstein J. Org. Chem. 2025, 21, 2383–2388, doi:10.3762/bjoc.21.183

• , The Ural Branch of Russian Academy of Sciences, Goleva St. 13, 614081 Perm, Russian Federation 10.3762/bjoc.21.183 Abstract A synthetic strategy for the preparation of spiro[indoline-3,2'-pyrrolidine] derivatives has been developed, featuring a two-step sequence consisting of the reaction of 2

Recent advances in Norrish–Yang cyclization and dicarbonyl photoredox reactions for natural product synthesis

• Peng-Xi Luo,
• Jin-Xuan Yang,
• Shao-Min Fu and
• Bo Liu

Beilstein J. Org. Chem. 2025, 21, 2315–2333, doi:10.3762/bjoc.21.177

• pyrrolidine-derived phenyl keto amide substrate 91 with blue LEDs produces the pyrrolidine-fused 4-oxazolidinone (N,O-acetal) 92, precluding preparation of the pyrrolidine analog of lycoplatyrine A (94) by this method. Compound 92 is presumably formed via either the radical mechanism [41] or possibly