Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

• Long K. San,
• Sebastian Balser,
• Brian J. Reeves,
• Tyler T. Clikeman,
• Yu-Sheng Chen,
• Steven H. Strauss and
• Olga V. Boltalina

Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39

• Barnstead NANOpure Ultrapure Water system, producing water with a final resistance of at least 18 MΩ); and silica gel (Sigma-Aldrich, 70–230 mesh, 60 Å). For HPLC separations: acetonitrile (Fisher Scientific ACS grade); toluene (Fisher Scientific, ACS grade); and heptane (Mallinckrodt Chemicals, ACS grade

• were extracted with Et2O and washed four to six times with doubly distilled water removing the aqueous layer each time. Anhydrous MgSO4 was added to the organic layer and passed through silica gel with DCM as the eluent. The organic layer was then concentrated to dryness. Yield (isolated): 9-H-10-BnF

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

• chlorine gas, with the reaction conducted by stirring the pyrazolinone with TCICA in DCM for 18 hours. Bimanes can be purified easily using column chromatography with silica gel as the stationary phase, with the compounds Cl2B, Me2B, and Me4B only requiring neat DCM as the eluent. After chromatographic

Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction

• James Guevara-Pulido,
• Fernando González-Pérez,
• José M. Andrés and
• Rafael Pedrosa

Beilstein J. Org. Chem. 2025, 21, 473–482, doi:10.3762/bjoc.21.34

• its enantioselectivity, aliquots of the reaction mixture were taken at defined time intervals and analyzed by HPLC using a chiral column after passing them through a short silica gel pad. Some interesting conclusions can be made from the data in Table 1. Firstly, the retro-Michael reaction occurs, to

• a one dm path length, and concentration was given in grams per 100 mL. TLC analysis was performed on glass-backed plates coated with silica gel 60 and an F254 indicator and visualized by either UV irradiation or staining with phosphomolybdic acid solution. Flash chromatography uses silica gel (230

• added to a solution of enal (2.5 mmol) and 2-phenylacetophenone (3.0 mmol) in dichloromethane (20 mL), and the mixture was stirred until the reaction was completed. Then, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using hexane/ethyl

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

• (9.1) (Scheme 9) [75]. In this case the authors used a ball-mill reactor equipped with a blue LED, and the reaction was run in a glass vial with two transparent PMMA balls. The authors noted that fluorination of the vial and the use of silica gel to adjust texture were needed to prevent reagent

• investigated. When o-terphenyl (10.1) was milled (30 Hz, PTFE balls) and irradiated (λ = 270 nm) in the presence of silica gel (bulking agent), I2 (1 equiv) as an oxidant, and K2CO3 (1 equiv) as a base in the presence of toluene, the expected product 10.2 was obtained in 81% yield after isolation upon 181 h of

Identification and removal of a cryptic impurity in pomalidomide-PEG based PROTAC

• Bingnan Wang,
• Yong Lu and
• Chuo Chen

Beilstein J. Org. Chem. 2025, 21, 407–411, doi:10.3762/bjoc.21.28

• to generate an inseparable byproduct. By contrast, the byproduct derived from Boc-protected amines has a significantly different retention time on HPLC and could be removed by regular silica gel chromatography. Because the formation of 5‒7 posts a significant purification challenge, we sought to

• silica gel column chromatography. The LUMO and electrostatic charges of thalidomide and its derivatives by DFT calculation at the ωB97X-D/6-311+G** level. The synthetic route for iVeliparib-AP6. The conversion of byproduct 6 to 10 to facilitate its removal. Effects of the length and functionalization of

Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia

• Rita Toshe,
• Syeda J. Khalid,
• Blondelle Matio Kemkuignou,
• Esteban Charria-Girón,
• Paul Eckhardt,
• Birthe Sandargo,
• Kunlapat Nuchthien,
• J. Jennifer Luangsa-ard,
• Till Opatz,
• Hedda Schrey,
• Sherif S. Ebada and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 327–339, doi:10.3762/bjoc.21.23

• (15 g) was analyzed by LC–MS. Thereafter, it was fractionated by vacuum liquid chromatography (VLC) using silica gel as a stationary phase. The elution procedure was performed using a chromatographic scheme of two different gradients as follows: 1) n-heptane/EtOAc (1:0, 7:3, 3:7, 0:1) followed by

Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions

• Dmitry E. Shybanov,
• Maxim E. Kukushkin,
• Eugene V. Babaev,
• Nikolai V. Zyk and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 262–269, doi:10.3762/bjoc.21.18

• days (TLC or NMR control). After completion of the reaction, the solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel using chloroform as eluent. ((1S,4S)-Bicyclo[2.2.1]hept-5-ene-2,2-diyl)bis(phenylmethanone) (8) and phenyl((4aR,7aS)-2-phenyl

Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory

• Misato Suganuma,
• Daichi Kitagawa,
• Shota Hamatani and
• Seiya Kobatake

Beilstein J. Org. Chem. 2025, 21, 242–252, doi:10.3762/bjoc.21.16

• solution, extracted with ether, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using n-hexane and ethyl acetate 95:5 to give 1.4 g of I2(a) in 50% yield. 1H NMR (300 MHz, CDCl3, TMS) δ = 2.55 (d, JHF = 3.2 Hz

• brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using n-hexane to give 2.8 g of I4(a) in 56% yield. 1H NMR (300 MHz, CDCl3, TMS) δ = 2.42 (s, 3H, CH3), 7.29–7.34 (m, 1H, aromatic H), 7.40–7.46 (m, 1H, aromatic H), 7.49

• reaction mixture was neutralized by HCl aqueous solution, extracted with ether, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using n-hexane and ethyl acetate 8:2 and recycling HPLC using chloroform as the

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

• JMS-T100GCV or a JEOL JMS-T200GC spectrometer. All the reactions were conducted under argon or nitrogen. Materials: Column chromatography was conducted on silica gel (Silica Gel 60 N, Kanto Chemical Co., Inc.). Toluene and N,N-dimethylformamide (DMF) were purified by a solvent-purification system

• . After removal of the solvent under reduced pressure, the residue was purified by silica gel column chromatography (hexane/EtOAc = 10:1) to give 3bb (76 mg, 98%) as a white solid. 1H NMR (500 MHz, CDCl3) δ 8.15 (d, J = 8.2 Hz, 1H), 7.93 (d, J = 8.2 Hz, 1H), 7.75–7.67 (m, 4H), 7.58 (ddd, J = 8.2, 6.9, 1.2

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

• products once experiments are performed. Despite this bottleneck, the landscape is evolving, with various practical tools emerging to streamline purification processes. From prepacked silica gel tubes to the precision semipreparative liquid chromatography and the versatile capabilities of various scavenger

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

• dichloromethane (2 mL) three times. The combined organic extracts were repeatedly washed with water (20 mL) and brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude material, which was purified by silica gel column chromatography (hexane

Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina

• Shin-ichiro Kurimoto,
• Kouta Inoue,
• Taito Ohno and
• Takaaki Kubota

Beilstein J. Org. Chem. 2024, 20, 3215–3220, doi:10.3762/bjoc.20.267

• , after which the extract was partitioned between EtOAc and H2O. The EtOAc-soluble fraction was subjected to silica gel column chromatography. A detailed analysis of the 1H NMR spectrum of the fraction eluted after the one containing ceratinadins E and F revealed signals corresponding to psammaplysin F (2

• sponge Pseudoceratina sp. (order Verongida; family Aplysinellidae), collected in Okinawa, Japan (0.4 kg, wet weight), was obtained following the method described in [8]. In a manner similar to [8], a portion of the EtOAc-soluble material (1.45 g) was fractionated by silica gel column chromatography

• [silica gel 60N (spherical, neutral, 40–50 µm), Kanto Chemical Co., Inc.; 38 × 350 mm; eluent CHCl3/MeOH 100:0 to 0:100], yielding 18 fractions (Fr. 1–18). A portion (17.0 mg) of the fraction Fr. 14 (32.5 mg) was further separated by C18 HPLC (COSMOSIL 5C18-AR-II, 10 × 250 mm, Nacalai tesque Inc.; eluent

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

• vial was quickly capped with a Teflon microwave cap. The reaction was heated to 70 ºC for 10 min. The crude mixture was dissolved with DCM (3 mL), the solvent was removed under reduced pressure to furnish a crude product that was purified by flash column chromatography, using silica gel 60 (200–400

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

• products. These highly stable compounds were isolated after purification on silica gel in good yields (Scheme 2) and characterized by spectroscopic methods. The reaction proceeded with very high Z-stereoselectivity (Scheme 2, compounds 9a–d). In the 19F NMR spectra of crude mixtures, only trace amounts of

C–H Trifluoromethylthiolation of aldehyde hydrazones

• Victor Levet,
• Balu Ramesh,
• Congyang Wang and
• Tatiana Besset

Beilstein J. Org. Chem. 2024, 20, 2883–2890, doi:10.3762/bjoc.20.242

• collected separately, dried over MgSO4, and concentrated in vacuo. The crude was purified by column chromatography on silica gel, flash chromatography to afford the desired product 2–6. State of the art and this work. Reaction conditions: hydrazone (0.3 mmol, 1.0 equiv), NBS (0.33 mmol, 1.1 equiv), in CH3CN

Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions

• Marzieh Norouzi,
• Mohammad Taghi Nazeri,
• Ahmad Shaabani and
• Behrouz Notash

Beilstein J. Org. Chem. 2024, 20, 2870–2882, doi:10.3762/bjoc.20.241

• reaction mixture was stirred at temperatures of 100 or 80 °C for 2 h using a magnetic stirrer. After making sure that the reactions were completed (monitored by TLC), the reaction mixture was cooled to ambient temperature. Then, the crude mixture was purified using a silica gel chromatography column and

Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates

• Kento Iwai,
• Akari Hikasa,
• Kotaro Yoshioka,
• Shinki Tani,
• Kazuto Umezu and
• Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2024, 20, 2827–2833, doi:10.3762/bjoc.20.238

•  3) [13][14]. To a dry THF solution of adduct 4a, butyllithium was added, and the reaction mixture was stirred at −78 °C for 5 min. Following the addition of acetic acid, the reaction mixture was concentrated and subjected to silica gel column chromatography, resulting in the isolation of ethyl 5

• ), the mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate 70:30, Rf 0.55) to afford diethyl 2-[(4-methylbenzoyl)amino]-2-(phenylethynyl)propanedioate (4a, 122 mg, 0.31 mmol, 78% yield) as yellow oil. 1H NMR (400

• acetic acid (0.1 mL), the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate 70:30, eluent for TLC: hexane/ethyl acetate 80:20, Rf 0.61) to afford ethyl 2-(4-methylphenyl)-5-(phenylmethyl)oxazole-4-carboxylate (5a

Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light

• Francesco Gambuti,
• Jacopo Pizzorno,
• Chiara Lambruschini,
• Renata Riva and
• Lisa Moni

Beilstein J. Org. Chem. 2024, 20, 2722–2731, doi:10.3762/bjoc.20.230

• yield of 88% each step). Since, during the optimization of the reaction conditions, we have noticed a certain instability of the spiro-compounds through chromatography on silica gel, we have initially carried out the purifications using alumina as the stationary phase. However, during the scope studies

• the solvent and using Et3N as additive for the eluent of the chromatography on silica gel. With these improvements, we have demonstrated that the yields are comparable to those obtained with purification on alumina but reaching significantly higher degrees of purity of the final products (see

• %) due to difficulties in the purification. IR spectra were recorded as solid, oil, or foamy samples, with the ATR (attenuated total reflectance) method. TLC analyses were carried out on pre-coated Merck silica gel 60 F254 plates or Aluminum oxide on TLC-plates and viewed at UV (254 nm) and developed

Synthesis of benzo[f]quinazoline-1,3(2H,4H)-diones

• Ruben Manuel Figueira de Abreu,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2708–2719, doi:10.3762/bjoc.20.228

• -Flight (TOF) LC–MS. The solvent, toluene, was purchased as dry solvent and applied without further purification. Other reagents, catalysts, ligands, acids, and bases were used as purchased from commercial suppliers. Column chromatography was performed on Merck Silica gel 60 (particle size 63–200 μm

Transition-metal-free decarbonylation–oxidation of 3-arylbenzofuran-2(3H)-ones: access to 2-hydroxybenzophenones

• Bhaskar B. Dhotare,
• Seema V. Kanojia,
• Chahna K. Sakhiya,
• Amey Wadawale and
• Dibakar Goswami

Beilstein J. Org. Chem. 2024, 20, 2655–2667, doi:10.3762/bjoc.20.223

• vacuum, and the residue was purified using silica-gel column chromatography. Compounds 3aa [21], 3ba [21], 3ea [21], 3eb [21], 3fa [21], 3fb [22], 3ga [21], and 3ja [21] were synthesized using the similar method as reported previously by us. General procedure for the synthesis of 2-hydroxybenzophenones

The scent gland composition of the Mangshan pit viper, Protobothrops mangshanensis

• Jonas Holste,
• Paul Weldon,
• Donald Boyer and
• Stefan Schulz

Beilstein J. Org. Chem. 2024, 20, 2644–2654, doi:10.3762/bjoc.20.222

• analysis [8]. Silver nitrate column chromatography: Silver nitrate column chromatography was carried out as described [45]. An aq solution of silver nitrate (5.5 g) in H2O (30 mL) was added to silica gel (50 g). Water was added to barely cover the silica gel. The silica was stirred with a glass rod and

• shaken for 15 min and then placed in an oven at 100 °C until the silica gel was completely dried. The impregnated silica gel was stored in the dark until use. Syntheses 1-(1-Propen-1-yl)piperidine (2): In a manner analogous to [27], potassium carbonate (2 g, 15 mmol), piperidine (10 mL, 0.1 mol), and

Synthesis and cytotoxicity studies of novel N-arylbenzo[h]quinazolin-2-amines

• Battini Veeraiah,
• Kishore Ramineni,
• Dabbugoddu Brahmaiah,
• Nangunoori Sampath Kumar,
• Hélène Solhi,
• Rémy Le Guevel,
• Chada Raji Reddy,
• Frédéric Justaud and
• René Grée

Beilstein J. Org. Chem. 2024, 20, 2592–2598, doi:10.3762/bjoc.20.218

• traces of residual moisture. Reactions were monitored by thin-layer chromatography (TLC) using E. Merck silica gel plates and components were visualized by illumination with short wavelength UV light and/or staining (ninhydrin or basic KMnO4). All aldehydes were distilled right before use. All aryl

Transition-metal-free synthesis of arylboronates via thermal generation of aryl radicals from triarylbismuthines in air

• Yuki Yamamoto,
• Yuki Konakazawa,
• Kohsuke Fujiwara and
• Akiya Ogawa

Beilstein J. Org. Chem. 2024, 20, 2577–2584, doi:10.3762/bjoc.20.216

• somewhat difficult due to strong adsorption or decomposition on silica gel. Since some arylboronates are somewhat unstable, it is desirable to synthesize such compounds and then use them in a one-pot manner for the following reactions without isolation. To gain insight into the reaction pathways, several

Anion-dependent ion-pairing assemblies of triazatriangulenium cation that interferes with stacking structures

• Yohei Haketa,
• Takuma Matsuda and
• Hiromitsu Maeda

Beilstein J. Org. Chem. 2024, 20, 2567–2576, doi:10.3762/bjoc.20.215

• sheets coated with silica gel 60 (Merck 5554). Column chromatography was performed on Wakogel C-300. Preparation of ion pairs 4,8,12-Tris(2,6-dimethylphenyl)-4,8,12-triazatriangulenium as a BF4− ion pair, 2+-BF4−. According to the literature procedure [26], to a Schlenk tube were added 2,6

• , 1.38 mmol), and the reaction mixture was stirred at rt for 10 min, followed by filtration, and evaporation to dryness. The residue was purified by silica gel column chromatography (Wakogel C-300; eluent: MeOH/AcOEt/CH2Cl2 1:2:8) and was recrystallized from CH2Cl2/n-hexane to afford 2+-BF4− (143 mg

• pair, 2+-PF6−. To a MeOH solution (3.0 mL) of 2+-BF4− (4.98 mg, 7.3 μmol) was added NaPF6 (3.68 mg, 22 μmol), and the reaction mixture was stirred at rt for 15 min, followed by filtration and evaporation to dryness. The residue was purified by silica gel column chromatography (Wakogel C-300; eluent: 5

Phenylseleno trifluoromethoxylation of alkenes

• Clément Delobel,
• Armen Panossian,
• Gilles Hanquet,
• Frédéric R. Leroux,
• Fabien Toulgoat and
• Thierry Billard

Beilstein J. Org. Chem. 2024, 20, 2434–2441, doi:10.3762/bjoc.20.207

• derivative 2k, and the estrone derivative 2l were also successfully bis-functionalized. Some products appeared to be sensitive during purification by chromatography on silica gel. Suspecting acid sensitivity, compound 2a was treated with trifluoroacetic acid to confirm this hypothesis (Scheme 3). The product