Ortho-ester-substituted diaryliodonium salts enabled regioselective arylocyclization of naphthols toward 3,4-benzocoumarins

• Ke Jiang,
• Cheng Pan,
• Limin Wang,
• Hao-Yang Wang and
• Jianwei Han

Beilstein J. Org. Chem. 2024, 20, 841–851, doi:10.3762/bjoc.20.76

• solvents including dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), toluene, acetic acid (AcOH) and water (Table 1, entries 9–13) were carried out. However, polar solvents such as AcOH and H2O were proved to be unsuitable for this reaction. For catalysts, we found that Cu(OAc)2 gave the best results

Palladium-catalyzed three-component radical-polar crossover carboamination of 1,3-dienes or allenes with diazo esters and amines

• Geng-Xin Liu,
• Xiao-Ting Jie,
• Ge-Jun Niu,
• Li-Sheng Yang,
• Xing-Lin Li,
• Jian Luo and
• Wen-Hao Hu

Beilstein J. Org. Chem. 2024, 20, 661–671, doi:10.3762/bjoc.20.59

• started our studies with the palladium-catalyzed MCR of ethyl diazoacetate (1a), 1,3-butadiene (2a), and 1-phenylpiperazine (3a) in the presence of 5 mol % Pd(OAc)2 and 10 mol % Xantphos as ligand. To our delight, after irradiation with blue LED light in dimethylformamide (DMF) for 12 h at room

Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

• conditions, particularly the solvent employed. For instance, when toluene is used as the reaction solvent, a reaction at 100 °C for 15 h affords an E/Z mixture of 7 (E/Z ≈ 1:1) with 90% yield, 8 with 10% yield, and 9 with 0% yield. In contrast, a reaction at 25 °C for 15 h in N,N-dimethylformamide (DMF

Selectivity control towards CO versus H₂ for photo-driven CO₂ reduction with a novel Co(II) catalyst

• Lisa-Lou Gracia,
• Philip Henkel,
• Olaf Fuhr and
• Claudia Bizzarri

Beilstein J. Org. Chem. 2023, 19, 1766–1775, doi:10.3762/bjoc.19.129

• -dimethylacetamide (DMA) as the major component. Although this solvent has very similar properties as the mostly used N,N-dimethylformamide (DMF), it is highly stable and does not produce formate upon hydrolysis [49]. In the solvent system DMA/TEOA 3:1 (v/v), we could observe that carbon monoxide was formed, however

Eschenmoser coupling reactions starting from primary thioamides. When do they work and when not?

• Lukáš Marek,
• Jiří Váňa,
• Jan Svoboda and
• Jiří Hanusek

Beilstein J. Org. Chem. 2023, 19, 808–819, doi:10.3762/bjoc.19.61

• . recommended [24] a polar aprotic solvent such as DMSO that facilitates the formation of both α-thioiminium salt (III) as well as Eschenmoser contraction involving the attack of the exposed carbanion towards the imine/iminium group (V). Based on our previous experience [3][4] we favor dimethylformamide (DMF

Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin

• János Máté Orosz,
• Dóra Ujj,
• Petr Kasal,
• Gábor Benkovics and
• Erika Bálint

Beilstein J. Org. Chem. 2023, 19, 294–302, doi:10.3762/bjoc.19.25

• the other hand, sodium azide in N,N-dimethylformamide (DMF) reacts with mono-6-O-tosyl-CDs to give CD monoazides in high yields. The obtained mono(6-azido-6-deoxy)-CDs (N3-CDs) are valuable precursors that can be used as starting materials in azide–alkyne click reactions; furthermore, they can be

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

• Solomiia Borova and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2023, 19, 217–230, doi:10.3762/bjoc.19.21

• -dimethylformamide (DMF), N-methyl-2-pyrrolidone (NMP), acetonitrile (MeCN), etc., have been added to the registration, evaluation, authorization and restriction of chemicals (REACH) list because of their negative environmental impact [1][2]. Therefore, the search for suitable solvents for the synthesis of synthetic

Ferrocenoyl-adenines: substituent effects on regioselective acylation

• Mateja Toma,
• Gabrijel Zubčić,
• Jasmina Lapić,
• Senka Djaković,
• Davor Šakić and
• Valerije Vrček

Beilstein J. Org. Chem. 2022, 18, 1270–1277, doi:10.3762/bjoc.18.133

• kinetic and thermodynamic control of the acylation reaction. Results and Discussion It was shown that the reaction between the pyrimidine anion (uracil, thymine, or 5-fluorouracil) and FcCOCl in N,N-dimethylformamide (DMF) proceeded in a full regiospecific mode [19]. In the purine series, however, the

Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate

• Hisanori Senboku,
• Mizuki Hayama and
• Hidetoshi Matsuno

Beilstein J. Org. Chem. 2022, 18, 1040–1046, doi:10.3762/bjoc.18.105

• ) [22][23]. We also succeeded in generating N-acyliminium ions from N,N-dimethylformamide (DMF) used as a solvent in the electrochemical carboxylation of benzyl bromides. Electrolysis of benzyl bromides in DMF containing 0.1 M Bu4NBF4 and iPr2NEt (1 equiv) using an undivided cell equipped with a Pt

Synthesis of bis-spirocyclic derivatives of 3-azabicyclo[3.1.0]hexane via cyclopropene cycloadditions to the stable azomethine ylide derived from Ruhemann's purple

• Alexander S. Filatov,
• Olesya V. Khoroshilova,
• Anna G. Larina,
• Vitali M. Boitsov and
• Alexander V. Stepakov

Beilstein J. Org. Chem. 2022, 18, 769–780, doi:10.3762/bjoc.18.77

• optimization of the reaction conditions for improving the yield of the cycloadduct 3a. A broad range of solvents was screened at different temperatures. As presented in Table 1, aprotic solvents such as 1,4-dioxane, acetonitrile, and dimethylformamide (DMF) at 65 °C favored the formation of the desired

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

• Umesh P. Aher,
• Dhananjai Srivastava,
• Girij P. Singh and
• Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

• into a primary alcohol with sodium borohydride affords compound 23. The protection of the hydroxy group of compound 23 was carried out by TBDPSCl in the presence of imidazole and N,N-dimethylformamide (DMF) as solvent, and deprotection of the benzoyl group by ammonolysis provides silylated compound 24

Chemical syntheses and salient features of azulene-containing homo- and copolymers

• Vijayendra S. Shetti

Beilstein J. Org. Chem. 2021, 17, 2164–2185, doi:10.3762/bjoc.17.139

• polyazulene 3 or 3’ was soluble in various organic solvents such as toluene, dichloromethane, tetrahydrofuran (THF), and N,N’-dimethylformamide (DMF). The ‘true polyazulene’ exhibited the conductivity of 5.38 × 10−8 S/cm, which was increased to 8.16 × 10−3 S/cm upon exposure to iodine atmosphere, presumably

Regioselective N-alkylation of the 1H-indazole scaffold; ring substituent and N-alkylating reagent effects on regioisomeric distribution

• Ryan M. Alam and
• John J. Keating

Beilstein J. Org. Chem. 2021, 17, 1939–1951, doi:10.3762/bjoc.17.127

• effect of varying these reaction parameters, using n-pentyl bromide as the prototypical N-alkylating reagent (Table 1). Early investigations revealed that the combination of cesium carbonate (Cs2CO3) in dimethylformamide (DMF) at room temperature (≈ 20 °C) afforded a mixture of N-1 and N-2 regioisomers

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

• Christopher Liczner,
• Kieran Duke,
• Gabrielle Juneau,
• Martin Egli and
• Christopher J. Wilds

Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76

• mixture of triethylammonium bicarbonate (TEAB) and N,N-dimethylformamide (DMF) followed by a sodium borohydride reduction to give the 4'-alkoxy products [202]. The 4'-methoxy-2'-deoxynucleosides exhibited high resistance towards depurination under acidic conditions [202]. In contrast, nucleosides that are

β-Lactamase inhibition profile of new amidine-substituted diazabicyclooctanes

• Zafar Iqbal,
• Lijuan Zhai,
• Yuanyu Gao,
• Dong Tang,
• Xueqin Ma,
• Jinbo Ji,
• Jian Sun,
• Jingwen Ji,
• Yuanbai Liu,
• Rui Jiang,
• Yangxiu Mu,
• Lili He,
• Haikang Yang and
• Zhixiang Yang

Beilstein J. Org. Chem. 2021, 17, 711–718, doi:10.3762/bjoc.17.60

• of S:R isomers = 6:1). The synthesis of intermediate 2 started from the hydrogenation of 7 by following a previously described method using N,N-dimethylformamide (DMF)/CH2Cl2 [23] as solvent led to a low yield in our hands. Therefore, we planned to switch the solvent from DMF to EtOAc whereupon the

Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones using an Eschenmoser coupling reaction

• Lukáš Marek,
• Lukáš Kolman,
• Jiří Váňa,
• Jan Svoboda and
• Jiří Hanusek

Beilstein J. Org. Chem. 2021, 17, 527–539, doi:10.3762/bjoc.17.47

• methanol) such an increase of acidity should be also distinct but it is known that polar protic solvents much better solvate anions and thus decrease their nucleophilicity. Therefore, dimethylformamide has been chosen as the best solvent. Indeed, when dimethylformamide (DMF) was used as the solvent for the

Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting

• Masayori Hagimori,
• Estefanía E. Mendoza-Ortega and
• Marie Pierre Krafft

Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45

• fluorine–fluorine interactions. Experimental Materials. We purchased Fmoc-protected amino acids, N,N-dimethylformamide (DMF), dichloromethane (DCM), methanol, 1-hydroxybenzotriazole (HOBT), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU), N,N-diisopropylethylamine (DIPEA

Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system

• Yamato Fujihira,
• Yumeng Liang,
• Makoto Ono,
• Kazuki Hirano,
• Takumi Kagawa and
• Norio Shibata

Beilstein J. Org. Chem. 2021, 17, 431–438, doi:10.3762/bjoc.17.39

• highly stable fluoride salts (MF), the breakdown of CF3− into difluorocarbene in the presence of alkali (M+) and other metal cations is favored. In earlier studies, the solvent N,N-dimethylformamide (DMF), was essential for nucleophilic trifluoromethylation by HCF3 since DMF acts as a CF3 anion reservoir

Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF₃)₂CHOH]

• Takeshi Fujita,
• Noriaki Shoji,
• Nao Yoshikawa and
• Junji Ichikawa

Beilstein J. Org. Chem. 2021, 17, 396–403, doi:10.3762/bjoc.17.35

• -Dimethylformamide (DMF) was purified by a solvent-purification system (GlassContour) equipped with columns of activated alumina and supported-copper catalyst (Q-5) before use. 1,1,1,3,3,3-Hexafluoropropan-2-ol (HFIP) was distilled from molecular sieves 4 Å and stored over activated molecular sieves 4 Å. 1,4-Dioxane

Thermodynamic and electrochemical study of tailor-made crown ethers for redox-switchable (pseudo)rotaxanes

• Henrik Hupatz,
• Marius Gaedke,
• Hendrik V. Schröder,
• Julia Beerhues,
• Arto Valkonen,
• Fabian Klautzsch,
• Sebastian Müller,
• Felix Witte,
• Kari Rissanen,
• Biprajit Sarkar and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2020, 16, 2576–2588, doi:10.3762/bjoc.16.209

• with a typical π-stacking distance of 3.58 Å and a tilt angle of 5.8°. The free electron pair of the tertiary amine points towards the inside of the crown ether. In contrast, single crystals of NDIC8 (Figure 2c), obtained by slow evaporation of a concentrated dimethylformamide (DMF) solution, exhibit a

Clustering and curation of electropherograms: an efficient method for analyzing large cohorts of capillary electrophoresis glycomic profiles for bioprocessing operations

• Ian Walsh,
• Matthew S. F. Choo,
• Sim Lyn Chiin,
• Amelia Mak,
• Shi Jie Tay,
• Pauline M. Rudd,
• Yang Yuansheng,
• Andre Choo,
• Ho Ying Swan and
• Terry Nguyen-Khuong

Beilstein J. Org. Chem. 2020, 16, 2087–2099, doi:10.3762/bjoc.16.176

• Reagent Solution (0.07 mg/µL in anhydrous dimethylformamide (DMF, Waters Corp.) was added to the released glycans, and the labelling proceeded at room temperature for 5 min. The reaction mixture was diluted by adding acetonitrile (ACN; final concentration 89.5%) in preparation for HILIC SPE. Purification

Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

• Alberto Rubin Pedrazzo,
• Fabrizio Caldera,
• Marco Zanetti,
• Silvia Lucia Appleton,
• Nilesh Kumar Dhakar and
• Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563, doi:10.3762/bjoc.16.127

• CD nanosponges, after crosslinking, comprise carbonate bonds between the cyclodextrin monomers. If this reaction is carried out under classical conditions in a N,N-dimethylformamide (DMF) solution, an amorphous crosslinked insoluble polymer is obtained. In general, carbonate nanosponges are insoluble

• , ReagentPlus® grade, ≥99%), methyl red, rhodamine B, and fluorescein (for all dyes, declared dye content 95%), N,N-dimethylformamide (DMF, anhydrous, 99.8%), acetone (ACS reagent, ≥99.5%), and ethanol (ACS reagent, 96%) were purchased from Sigma-Aldrich (Munich, Germany) and used without further purification

Synthesis and properties of quinazoline-based versatile exciplex-forming compounds

• Rasa Keruckiene,
• Simona Vekteryte,
• Ervinas Urbonas,
• Matas Guzauskas,
• Eigirdas Skuodis,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 1142–1153, doi:10.3762/bjoc.16.101

• compounds 1–3 were synthesized through nucleophilic substitution reactions between quinazoline derivative Q1 and the respective donor compound in the presence of sodium hydride in dry dimethylformamide (DMF). The reaction mixtures were refluxed for 24 h. After completion of the reactions, the reaction

• ): Quinazoline derivative (Q1, 0.25 g, 0.79 mmol), 3,6-di-tert-butylcarbazole (0.48 g, 1.7 mmol) and sodium hydride (0.50 g, 1.6 mmol) in dry dimethylformamide (DMF) were used for the nucleophilic substitution reaction. The title compound was obtained as yellowish crystals in a yield of 0.25 g, 37%; Tm = 181 °C

• mmol) and sodium hydride (0.50 g, 1.6 mmol) in dry dimethylformamide (DMF) were used for the nucleophilic substitution reaction. The title compound was obtained as yellowish crystals in a yield of 0.10 g, 21%; Tm = 233 °C; 1H NMR (400 MHz, CDCl3) δ 8.93 (s, 2H), 8.11 (s, 2H), 7.89-7.84 (s, 4H), 7.56 (s

Suzuki–Miyaura cross coupling is not an informative reaction to demonstrate the performance of new solvents

• James Sherwood

Beilstein J. Org. Chem. 2020, 16, 1001–1005, doi:10.3762/bjoc.16.89

• of Mizoroki–Heck reactions have a strong dependence on the dipolarity of the reaction medium, and the rate determining step can be controlled by the equivalents of ligand added, thereby eliminating one variable [8]. Reprotoxic solvents such as N,N-dimethylformamide (DMF) are routinely used in the

Accelerating fragment-based library generation by coupling high-performance photoreactors with benchtop analysis

• Quentin Lefebvre,
• Christophe Salomé and
• Thomas C. Fessard

Beilstein J. Org. Chem. 2020, 16, 982–988, doi:10.3762/bjoc.16.87

• were slightly altered: a smaller excess of amine was used, and dimethyl sulfoxide (DMSO) was chosen as solvent instead of dimethylformamide (DMF) or dimethylacetamide (DMA) to improve work-up and purification. The workflow was devised to ensure maximal productivity, using parallel experimentation