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

• ), 300 (0.5), 265 (0.6) 218 (2.4); NMR data (1H: 500 MHz, 13C: 125 MHz, DMSO-d6) see Table 1; HRESIMS m/z: [M – H2O + H]+ calcd for C25H28NO4+, 406.2026; found, 406.2020; [M + H]+ calcd for C25H30NO5+, 424.2118; found, 424.2126; [M + Na]+ calcd for C25H29NNaO5+, 446.1962; found, 446.1947. Farinosone A (2

• . Beauvericin A (4): Yellow solid powder; UV–vis (MeOH) λmax: 344, 221 nm; NMR data (1H: 500 MHz in DMSO-d6) comparable to the previously described spectral data [14][15]; HRESIMS m/z: [M + H]+ calcd for C46H60N3O9+, 798.4324; found, 798.4324; [M + NH4]+ calcd for C46H63N4O9+, 815.4590; found, 815.4588; [M + Na

• ]+ calcd for C46H59N3NaO9+, 820.4144; found, 820.4142. Beauvericin B (5): Yellow amorphous solid; UV–vis (MeOH) λmax: 344, 250, 210 nm; NMR data (1H: 500 MHz, DMSO-d6) comparable to the previously described spectral data [14][15]; HRESIMS m/z: [M + H]+ calcd for C47H62N3O9+, 812.4481; found, 812.4489; [M

Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles

• Yujun Pang,
• Jinglan Yan,
• Nawaf Al-Maharik,
• Qian Zhang,
• Zeguo Fang and
• Dong Li

Beilstein J. Org. Chem. 2025, 21, 234–241, doi:10.3762/bjoc.21.15

• transformation (Table 1, entries 2 and 3), and PIDA was the most efficient promoter. Changing THF to other solvents, such as DCM, EtOH, DMF, CH3CN, EtOAc, or DMSO, resulted in a lower yield (Table 1, entries 4–9). Furthermore, variations in the amounts of PIDA or CF2HCOOH led to diminished yields (Table 1

Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide

• Marios Zingiridis,
• Danae Papachristodoulou,
• Despoina Menegaki,
• Konstantinos G. Froudas and
• Constantinos G. Neochoritis

Beilstein J. Org. Chem. 2025, 21, 217–225, doi:10.3762/bjoc.21.13

• pyrimidine scaffold. Representative fluorescence spectrum of compounds 5b (λex = 330 nm) and 6e (λex = 430 nm) at 0.2 M in DMSO. Molecular geometry observed within the crystal structure of compound 7b (CCDC 2376493). Strategies towards targeted adducts: A) Niementowski quinazoline synthesis utilizing

• materials. The colored frames indicate the different scaffold types. Synthesis of N-substituted thienopyrimidones 5a–e by a Gewald three-component reaction employing 2-aminothiophenes 2a–e and formamide as C1 source. A characteristic fluorescence for compound 5a was reported (365 nm in DMSO). The reported

• yield refers to the overall two-step synthesis. Synthesis of N-substituted quinolinopyrimidones 6a–e from 2-aminoindoles 3a–e and formamide as C1 source. A characteristic fluorescence for compound 6c was reported (365 nm in DMSO). The reported yields refer to the overall two-step synthesis. Synthesis of

Quantifying the ability of the CF₂H group as a hydrogen bond donor

• Matthew E. Paolella,
• Daniel S. Honeycutt,
• Bradley M. Lipka,
• Jacob M. Goldberg and
• Fang Wang

Beilstein J. Org. Chem. 2025, 21, 189–199, doi:10.3762/bjoc.21.11

• by hydrogen bond acidity [47][48] which is derived from the 1H NMR chemical shift difference of a given proton in DMSO-d6 and CDCl3, the CF2H group is generally a stronger donor than the methyl group but substantially weaker than the OH or amide NH groups [19][20]. These results collectively indicate

• method [19][20][47][48]. This convenient approach relies on comparing the 1H NMR chemical shift of a hydrogen bond donor in DMSO-d6 to that of it in CDCl3. The HB donor presumably interacts strongly with hydrogen-accepting DMSO [51], but barely with CDCl3, which has a weak hydrogen bond acceptance

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

• with feedback DOE facilitated the rapid identification of appropriate solvents. Notably, the use of DMSO, DMF, and pyridine led to an enhanced yield of the monoalkylated product. An experimental setup was developed for single-droplet studies of visible-light photoredox catalysis using an oscillatory

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

• Merve Yence,
• Dilgam Ahmadli,
• Damla Surmeli,
• Umut Mert Karacaoğlu,
• Sujit Pal and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

• formation reaction. Pleasingly, benzo[j]fluoranthene 27 was obtained successfully via the Pd-catalyzed reaction of dibromonaphthalene 14 and naphthylboronic ester 26 in DMSO at 120 °C, albeit in a modest yield of 34%. A final basic hydrolysis of the acetoxy group furnished benzo[j]fluoranthene 23 bearing a

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

• . Cells were seeded at a density 2 × 103 cells/well (198 μL/well) in 96-well plates, and test samples dissolved in DMSO (2 μL) were added to each well. The cells were then incubated for 72 hours. Cell viability was assessed using a WST-8 [2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl

Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

• Sasha Hayes,
• Yaoying Lu,
• Bernd H. A. Rehm and
• Rohan A. Davis

Beilstein J. Org. Chem. 2024, 20, 3205–3214, doi:10.3762/bjoc.20.266

• brown gum. The LRESIMS of 4 indicated the presence of two bromine atoms due to a 1:2:1 ion cluster at m/z 459/461/463 [M + H]+, whilst the HRESIMS data allowed a molecular formula of C17H20Br2N2O3 to be assigned. The 1H NMR (Table 1) and edited HSQC spectra of 4 in DMSO-d6 indicated the presence of one

• . The 1H and 13C chemical shifts were referenced to solvent peaks for DMSO-d6 at δH 2.50 and δC 39.52, respectively. LRESIMS data was recorded on an Ultimate 3000 RS UHPLC coupled to a Thermo Fisher Scientific ISQEC single quadruple ESI mass spectrometer. HRESIMS data was acquired on a Bruker maXis II

• sufficient quantities of the minor natural products for characterisation and biological assessment with similar recoveries obtained. Ianthelliformisamine D (4): Stable brown gum; UV (MeOH) λmax, nm (log ε): 226 (4.01), 278 (3.86); 1H and 13C NMR data (DMSO-d6), see Table 1; LRESIMS (m/z): 459/461/463 [M + H

Surprising acidity for the methylene of 1,3-indenocorannulenes?

• Shi Liu,
• Märt Lõkov,
• Sofja Tshepelevitsh,
• Ivo Leito,
• Kim K. Baldridge and
• Jay S. Siegel

Beilstein J. Org. Chem. 2024, 20, 3144–3150, doi:10.3762/bjoc.20.260

• ; Loschmidt group element; molecular graph; Introduction A classic textbook tetrad linking hydrocarbon acidity to aromatic stabilization energy comprises cyclopentadiene (CpH), indene (InH), fluorene (FlH), and diphenylmethane (DPMH) [1][2], with pKa values in DMSO equal to 18 [3], 20.1 [3], 22.6 [3], and

• 32.2 [4], respectively (Scheme 1) [5][6]. The reaction enthalpy for deprotonation of CpH is ca 20 kcal/mol less endothermic than DPMH and ca. 24–27 kcal/mol less endothermic than 1,4-pentadiene (PDH; pKa ≈ 35 in DMSO) [3], values strikingly similar to the resonance stabilization energy estimated for

• (pKa = 34 in CH3CN), or fluorene (pKa = 37 in CH3CN), BFC and FIC rank as stronger acids than CpH in acetonitrile. Extrapolation to DMSO by conversion equations, supports the assertion that BFC and FIC are more acidic than CpH in an “absolute acidity” sense [13]. How odd is such a pKa value of ca. 14

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

• Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

• solutions [18]. Similarly, Burns and co-workers reported di- and tetra-urea picket porphyrins highlighting, the impact of buried solvent molecules, such as DMSO, on the selectivity, affinity, and stoichiometry of anion binding [19]. Iron complexes of tetra-urea picket porphyrins further demonstrate how

• ) using substituted anilines 101 and t-BuONO (Figure 18). The reactions were conducted under light irradiation (blue light/sunlight) for 30 minutes in DMSO within an inert atmosphere. All corroles demonstrated catalytic activity with only 0.5% loading, while control experiments without a catalyst or light

Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction

• Cesia M. Aguilar-Morales,
• América A. Frías-López,
• Nadia V. Emilio-Velázquez,
• Alejandro Islas-Jácome,
• Angelica Judith Granados-López,
• Jorge Gustavo Araujo-Huitrado,
• Yamilé López-Hernández,
• Hiram Hernández-López,
• Luis Chacón-García,
• Jesús Adrián López and
• Carlos J. Cortés-García

Beilstein J. Org. Chem. 2024, 20, 3077–3084, doi:10.3762/bjoc.20.256

• proposing new structures with improved activity. Differential effect of the 1,5-disubstituted tetrazole-indole hybrid compounds 18a–j on proliferation of MCF-7 cell line. MCF-7 cells were treated with increasing doses of compounds 18a–j. Controls were cells treated with DMSO. Synthetic approaches to obtain

Cyclodextrin-based rotaxanes for polymer materials: challenge on simultaneous realization of inexpensive production and defined structures

• Yosuke Akae

Beilstein J. Org. Chem. 2024, 20, 3026–3049, doi:10.3762/bjoc.20.252

• sulfoxide (DMSO) must be available as CD forms the inclusion complex), (5) the yield of the end-capping reaction must be high, (6) the end-capping reagent and rotaxane must dissolve in the same solvent to facilitate a homogeneous reaction, and (7) the rotaxane must be isolable from the reaction mixture. The

• -based [2]rotaxane exhibiting α-CD as the end-capping moiety (Figure 7B) [62]. The wheel was located on the methylene moiety in DMSO, although it moved to the stilbene moiety in water via inclusion formation between CD on the axle-end moiety and the methylene chain. When [3]rotaxane exhibiting another

• the urea end-capping synthesis method (Figure 9) [46][47]. First, [3]rotaxane 3 synthesized using 2-bromophenyl isocyanate (yield: 73%) was confirmed to be a size-complementary rotaxane whose desilippage was observed in a DMSO solvent by heating at approximately 80 °C (Figure 9A,B). As the

Tunable full-color dual-state (solution and solid) emission of push–pull molecules containing the 1-pyrindane moiety

• Anastasia I. Ershova,
• Sergey V. Fedoseev,
• Konstantin V. Lipin,
• Mikhail Yu. Ievlev,
• Oleg E. Nasakin and
• Oleg V. Ershov

Beilstein J. Org. Chem. 2024, 20, 3016–3025, doi:10.3762/bjoc.20.251

• the emission band was observed upon increasing the solvent polarity from carbon tetrachloride to DMSO, and the strongest fluorescence was registered in nonpolar medium (Φem = 87.5 % for compound 1c in toluene and Φem = 73.9% for compound 1i in CCl4). Slopes of the Lippert–Mataga plots (Figures S3 and

• even more pronounced for compound 1i than for 1c due to presence of the stronger electron-donating group. Then, the substituent effects on the spectral properties of stilbazoles 1a–i were studied in two different solvents: nonpolar toluene (Table 2) and highly polar DMSO (Table 3). The absorption

• only exceptions were compounds 1e and 1f, containing three methoxy groups. In these cases, a blue shift of the absorption band in comparison to the disubstituted derivative 1d was observed, which was apparently caused by a partial planarity violation due to steric hindrance. In DMSO, the absorption

Tailored charge-neutral self-assembled L₂Zn₂ container for taming oxalate

• David Ocklenburg and
• David Van Craen

Beilstein J. Org. Chem. 2024, 20, 3007–3015, doi:10.3762/bjoc.20.250

• connecting units for an easy ligand preparation (Figure 1b). The resulting compressed self-assembled host with a non-planar ligand backbone is the first charge-neutral metallocontainer able to bind oxalate forming a 1:1 host–guest complex with a binding constant of log K = 4.39 ± 0.04 in DMSO as highly

• troubles with the formed complexes in this respect. The final step of the ligand preparation is the CuAAC click reaction. The protecting Boc group of the 8-hydroxyquinoline units was cleaved during the workup right away resulting in ligand L-H2 with 44% yield. Self-assembly in DMSO with zinc(II) via its

• acetate salt results in a charge-neutral and bench-stable [L2Zn2] metallocontainer. Purification of the complex is achieved by lyophilization which accomplishes the removal of acetic acid as only byproduct of the complexation reaction and DMSO as solvent. The charge-neutral receptor is obtained as a

Advances in radical peroxidation with hydroperoxides

• Oleg V. Bityukov,
• Pavel Yu. Serdyuchenko,
• Andrey S. Kirillov,
• Gennady I. Nikishin,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2024, 20, 2959–3006, doi:10.3762/bjoc.20.249

• TBHP was developed (Scheme 41) [99]. The reaction proceeds in DMSO at 65 °C, the resulting β-peroxy alcohols 121 were isolated in good yields. It is assumed that in the first step, the reaction of TBHP with a low-valent metal forms tert-butoxy radical A, and that the resulting M(n+1)OH species provide

Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

• Ritu Mamgain,
• Kokila Sakthivel and
• Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

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

• information All commercially available reagents and chemicals were bought from Merck & Co. and utilized without extra purification. The melting points of all synthesized compounds were measured utilizing an Electrothermal 9200 apparatus. 1H and 13C NMR and spectra in CDCl3 and DMSO-d6 solvents were recorded

• nuclear magnetic resonance) spectra of compound 6f (DMSO-d6, 300 MHz) at 25–85 °C; spectrum A: 25 °C, spectrum B: 35 °C, spectrum C: 45 °C, spectrum D: 55 °C, spectrum E: 65 °C, spectrum F: 75 °C and spectrum E: 85 °C. The crystal structure of 6a (CCDC2365306). UV–vis absorption for compounds 4a, 6c and

Investigation of a bimetallic terbium(III)/copper(II) chemosensor for the detection of aqueous hydrogen sulfide

• Parvathy Mini,
• Michael R. Grace,
• Genevieve H. Dennison and
• Kellie L. Tuck

Beilstein J. Org. Chem. 2024, 20, 2818–2826, doi:10.3762/bjoc.20.237

• -DPA)3]3−, Tb.1 exhibited limited solubility in water, becoming insoluble at concentrations exceeding 100 μM. Therefore, a 1 mM stock solution of Tb.1 was prepared in DMSO, with the final concentration of DMSO in analytical solutions kept at ≤5%. Initial luminescence analysis of a 5 μM solution of Tb.1

• ). Response of Tb.1 with Cu2+ ions The addition of excess Cu2+ ions to Tb.1 was expected to result in complete saturation of emission signals. However, upon the titration of Cu2+ ions to 5 μM Tb.1 (10 mM Tris-HCl buffer containing 5% DMSO, pH 7.4), emission signal saturation was not observed until 5

• containing 5% DMSO, pH 7.4 was used (Figure S4 in Supporting Information File 1), with a similar degree of quenching to that observed in 10 mM Tris-HCl buffer. The incomplete quenching in luminescence was previously also observed for the Eu(III)/Cu(II) complex [16]. Supramolecular.org [18], an Open Access

Interaction of a pyrene derivative with cationic [60]fullerene in phospholipid membranes and its effects on photodynamic actions

• Hayato Takagi,
• Çetin Çelik,
• Ryosuke Fukuda,
• Qi Guo,
• Tomohiro Higashino,
• Hiroshi Imahori,
• Yoko Yamakoshi and
• Tatsuya Murakami

Beilstein J. Org. Chem. 2024, 20, 2732–2738, doi:10.3762/bjoc.20.231

• -methyl-1-pyrrolidone-N-oxide (DEPMPO) were respectively used (schemes in Figure 5). Our previous study demonstrated that both 1O2 and O2•– were generated under irradiation of triad molecules in DMSO/H2O [8]. Under irradiation by a blue LED (464–477 nm, 23 lm·W–1), significant ESR signals corresponding to

• inability of O2•– detection is not known at present. Upon addition of dimethyl sulfoxide (DMSO) to this system, an adduct of DEPMPO and •CH3 (DEPMPO-CH3), which was presumably generated from the reaction of •OH and DMSO, was clearly observed, further confirming the generation of •OH (Figure 5b(iii)). At the

• Plains, NY, USA) was solubilized in ethanol (FUJIFILM Wako Pure Chemical Corporation, Osaka, Japan), and catC60, which was synthesized according to a previous report [20], or C60 (NOF AMERICA Corporation, White Plains, NY, USA) was solubilized in a 1:4 (vol:vol) mixture of DMSO (Nacalai Tesque Inc

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

• (right, λex = 400 nm) spectra of 5a, 5d, 5f, 5g, 5h, and 5i in dichloromethane (c = 1⋅10−5 M). Strategy for the synthesis of the cyclised product 5. Conditions: i) Br2 (2 equiv), Ac2O (1.5 equiv), AcOH, 25 °C, 1 h [65]; ii) Pd(PPh3)Cl2 (5 mol %), CuI (5 mol %), NEt3 (10 equiv), DMSO, 25 °C, 6 h; iii) Pd

Efficient modification of peroxydisulfate oxidation reactions of nitrogen-containing heterocycles 6-methyluracil and pyridine

• Alfiya R. Gimadieva,
• Yuliya Z. Khazimullina,
• Aigiza A. Gilimkhanova and
• Akhat G. Mustafin

Beilstein J. Org. Chem. 2024, 20, 2599–2607, doi:10.3762/bjoc.20.219

• classes. Experimental 1H and 13C NMR spectra were recorded on a Bruker Avance III 500 MHz spectrometer at 500.13 MHz (1H) and 125.73 MHz (13C) with 5 mm QNP sensors at a constant sample temperature of 298 K. The solvents were DMSO-d6, D2O, CDCl3 and the internal standard was SiMe4. Chemical shifts in the

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

• bromides and other reagents were used as they were received from commercial suppliers, unless otherwise noted. THF and Et2O were dried over sodium-benzophenone and distilled prior to use. 1H NMR spectra were recorded at 300 and 400 MHz, and 13C NMR spectra at 75 and 100 MHz, in CDCl3 or DMSO-d6 using TMS

• reduced pressure to afford crude compound 2 as pale-yellow solid (65% yield). Its NMR data are in agreement with literature [5]. 1H NMR (400 MHz, DMSO-d6, δ ppm) 10.49 (s, 1H), 8.26 (d, J = 8.4 Hz, 1H), 8.10 (d, J = 8.0 Hz, 1H), 7.90 (d, J = 8.8 Hz, 1H), 7.84–7.74 (m, 3H). Step 2: Synthesis of benzo[h

• , filtered and dried to get compound 3 as a brown colored solid (63% yield). 1H NMR (400 MHz, DMSO-d6, δ ppm) 9.06 (s, 1H), 8.91 (d, J = 8.0 Hz, 1H), 7.93 (d, J = 7.6 Hz, 1H), 7.76–7.64 (m, 3H), 7.56 (d, J = 8.8 Hz, 1H), 6.99 (br s, 2H); 13C NMR (75 MHz, DMSO-d6, δ ppm) 162.18, 161.31, 152.03, 136.05, 130.07

Base-promoted cascade recyclization of allomaltol derivatives containing an amide fragment into substituted 3-(1-hydroxyethylidene)tetronic acids

• Andrey N. Komogortsev,
• Constantine V. Milyutin and
• Boris V. Lichitsky

Beilstein J. Org. Chem. 2024, 20, 2585–2591, doi:10.3762/bjoc.20.217

• Unless otherwise stated, all starting chemicals were commercially available and were used as received. The starting compounds 1 were prepared by a procedure described in the literature [33][34]. NMR spectra were recorded with Bruker AM 300 (300 MHz) in DMSO-d6. Chemical shifts (ppm) are given relative to

• solvent signals (DMSO-d6: 2.50 ppm (1H NMR) and 39.52 ppm (13C NMR)). High-resolution mass spectra (HRMS) were obtained on a Bruker micrOTOF II instrument using electrospray ionization (ESI). The melting points were determined on a Kofler hot stage apparatus. A magnetic stirrer IKA C-MAG HS 7 was used for

• -ylidene)furan-2,4(3H,5H)-dione (4a). Pale yellow powder; yield 62% (0.25 g); mp 121–123 °C; 1H NMR (300 MHz, DMSO-d6) δ 7.31–7.13 (m, 5H), 4.34 (t, J = 7.5 Hz, 2H), 2.74 (t, J = 7.6 Hz, 2H), 2.56–2.48 (m, 2H in DMSO), 2.46 (s, 3H), 2.14 (t, J = 11.8 Hz, 2H), 1.64–1.54 (m, 3H), 1.41–1.09 (m, 5H); 13C NMR

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

• quantitatively (Table 1, entry 8). Furthermore, instead of BTF, the reaction was carried out with similarly polar CHCl3, polar and aprotic CH3CN, DMF, DMSO, and protic EtOH, and it was found that BTF was the optimal solvent for the synthesis of 3a (Table 1, entry 2 vs entries 9–13). Based on the optimized

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

• anode and a foamed Ni cathode, at a constant current of 12 mA in DMSO at room temperature under atmospheric conditions. The reaction has been applied to more than 80 examples, including the late-stage functionalization of natural products and pharmaceuticals, as well as the synthesis and radiosynthesis