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

• , to facilitate the aryldifluoromethylation of N-arylacrylamides. Experiments demonstrated that using 8Br-4CzIPN as the photocatalyst and tetrabutylammonium hydroxide as the base in ethyl acetate yielded the best results [15]. A variety of substrates were tested to assess the generality of the reaction

On Reuben G. Jones synthesis of 2-hydroxypyrazines

• Pierre Legrand and
• Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 935–943, doi:10.3762/bjoc.18.93

• % tetrabutylammonium hydroxide solution instead of sodium hydroxide as a base (Table 1; entry 10) but, in this case and as compared with entry 3, only a marginally greater 76% yield of compound 3{1,1} was obtained. Another puzzling result found in the course of these trials, is the yield of isolated compound 3{1,1

• occurrence of modest amounts of isomer 4{1,2}. Of note is that the use of sodium ethoxide was not successful (Table 2, entry 13) whereas the use of 0.75 N tetrabutylammonium hydroxide either diluted in water or in methanol (Table 2, entries 14 and 15) had the biggest impact on the reaction yield

• . Interestingly, if yield and regioselectivity-wise a sodium hydroxide addition at 20 °C was disastrous (Table 2, entry 16), only a 10% yield loss (and no regioselectivity changes) was seen when using tetrabutylammonium hydroxide instead (Table 2, entry 17). Further trials using tetraethylammonium hydroxide

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

Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

• Anka Utama Putra,
• Deniz Çakmaz,
• Nurgül Seferoğlu,
• Alberto Barsella and
• Zeynel Seferoğlu

Beilstein J. Org. Chem. 2020, 16, 2282–2296, doi:10.3762/bjoc.16.189

• -pull dyes are promising candidate materials for optoelectronic device usages and various NLO applications and could be used for applications as water-soluble fluorescent probes for determination of pH. Experimental Materials, methods, and instrumentation Tetrabutylammonium hydroxide (TBAOH) was

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

• Rafia Siddiqui and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

• of various bases, however, the best results were obtained with tetrabutylammonium hydroxide (TBAOH). The suggested mechanism commences with the photoexcitation of photocatalyst 11 to a strongly oxidizing excited state 50 (E1/2 red([Ru(bpy)3]2+*/[Ru(bpy)]3+) = +0.77 V vs SCE). Then, SET from anion 52

Easy, efficient and versatile one-pot synthesis of Janus-type-substituted fullerenols

• Marius Kunkel and
• Sebastian Polarz

Beilstein J. Org. Chem. 2019, 15, 901–905, doi:10.3762/bjoc.15.87

• tetrabutylammonium hydroxide (0.5 mL of a 30% solution in H2O). The reactants for the polyhydroxylation are added, H2O2 (1.5 mL of a 30% solution) and NaOH (0.7 g). The mixture is heated to reflux until the chlorobenzene phase decolorizes. The reaction is completed after 2 h of reflux. The aqueous phase is separated

Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles

• Takashi Go,
• Akane Morimatsu,
• Hiroaki Wasada,
• Genzoh Tanabe,
• Osamu Muraoka,
• Yoshiharu Sawada and
• Mitsuhiro Yoshimatsu

Beilstein J. Org. Chem. 2018, 14, 2722–2729, doi:10.3762/bjoc.14.250

• -sulfinyl- and seleninylpyrroles was described. The usual Pummerer reaction of 4-(alkenylaminomethyl)-3-phenylsulfinylpyrroles and a successive reaction with tetrabutylammonium hydroxide (TBAH) yielded either pyrrolo[3,2-c]azepines or N-pyrrol-3-ylmethyl-N-(4-hydroxy-3-sulfanylpropyl)-p-toluenesulfonamides

• usual Pummerer reaction, followed by treatment with bases at −20 °C (Table 1, entries 8–10). We determined that the S-shift reaction was strongly affected by the base. Tetrabutylammonium hydroxide was found to be the best base for the formation of 9a (Table 1, entry 10). Neither trimethylsilyl

Two strategies for the synthesis of the biologically important ATP analogue ApppI, at a multi-milligram scale

• Janne Weisell,
• Jouko Vepsäläinen and
• Petri A. Turhanen

Beilstein J. Org. Chem. 2015, 11, 2189–2193, doi:10.3762/bjoc.11.237

• addition of 2 equiv of 40% tetrabutylammonium hydroxide in H2O. The ApppI tris(triethylammonium) salt was converted into the disodium salt by the same method except that 0.1 M NaOH solution was used (see additional 13C NMR spectrum in Supporting Information File 1). The solvent residual peak was used as a

Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones

• Flavia Pop and
• Narcis Avarvari

Beilstein J. Org. Chem. 2015, 11, 1105–1111, doi:10.3762/bjoc.11.124

• enantiomeric DM-EDT-TTF-dithiopropionitriles (S,S)-3 and (R,R)-3 as the major products. Tetrabutylammonium hydroxide was then used to generate the corresponding dithiolates 2 in THF that, after solvent evaporation during which air was allowed in the Schlenk tube, were further refluxed in acetonitrile with 1,2

• , 3.08; N, 5.32; S, 52.51 (%). DM-BEDT-TTF monosulfone (S,S)-1: After the solution of (S,S)-3 (100 mg, 0.2 mmol) in 7 mL of dry THF was degassed for 10 min by bubbling argon through the solution, tetrabutylammonium hydroxide solution (1 M in methanol, 0.44 mL, 0.44 mmol) was added and the mixture was

A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3-butyn-2-ols

• Jie Li and
• Pengcheng Huang

Beilstein J. Org. Chem. 2011, 7, 426–431, doi:10.3762/bjoc.7.55

• Jie Li Pengcheng Huang Department of Polymer Materials and Composites, School of Materials Science and Engineering, Beihang University, Beijing 100191, China 10.3762/bjoc.7.55 Abstract Tetrabutylammonium hydroxide with methanol as an additive was found to be a highly active catalyst for the

• reaction time under much milder conditions. Keywords: 4-aryl-2-methyl-3-butyn-2-ol; deprotection reaction; 2-methyl-3-butyn-2-ol; terminal alkynes; tetrabutylammonium hydroxide; Introduction Terminal arylacetylenes are key precursors for the construction of conjugated oligo- or polyarylacetylenes, which

• limit the application of MEBYNOL in the preparation of terminal arylacetylenes. To solve the problem, herein we report a novel efficient catalyst system consisting of tetrabutylammonium hydroxide (Bu4NOH) and methanol for the removal of the 2-hydroxypropyl group from 4-aryl-2-methyl-3-butyn-2-ols under

Anion–π interactions influence pK_a values

• Christopher J. Cadman and
• Anna K. Croft

Beilstein J. Org. Chem. 2011, 7, 320–328, doi:10.3762/bjoc.7.42

• measured by potentiometric titration in 50:50 mixtures of acetonitrile/water with tetrabutylammonium hydroxide (TBAH) as the base. As an example, the plot obtained for compound 1 with TBAH is shown in Figure 3. The derived pKa' values, along with the Hammett σp-constant for each R-substituent are presented

Effects of anion complexation on the photoreactivity of bisureido- and bisthioureido-substituted dibenzobarrelene derivatives

• Heiko Ihmels and
• Jia Luo

Beilstein J. Org. Chem. 2011, 7, 278–289, doi:10.3762/bjoc.7.37

• . Bodenstedt, Organic Chemistry I, University of Siegen. TLC analyses were performed on silica-gel sheets (Macherey-Nagel Polygram Sil G/UV254). Unless otherwise mentioned, commercially available chemicals were reagent grade and were used without further purification. Tetrabutylammonium hydroxide in MeOH (1.0

• acids: The tetrabutylammonium salts of the chiral carboxylates SMD, RMD, RTZ, and SCP were prepared by the neutralization of the corresponding chiral acids with tetrabutylammonium hydroxide (1.0 M in MeOH) [56]. The resulting salts were used as 0.1 M stock solutions in acetone. The tetrabutylammonium

A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative

• Zhipei Yang,
• Kai Zhang,
• Fangbin Gong,
• Shayu Li,
• Jun Chen,
• Jin Shi Ma,
• Lyubov N. Sobenina,
• Albina I. Mikhaleva,
• Guoqiang Yang and
• Boris A. Trofimov

Beilstein J. Org. Chem. 2011, 7, 46–52, doi:10.3762/bjoc.7.8

• log K2 = 6.38 ± 0.15, respectively [17][18] (Figure 7). Studies on reaction with hydroxide (OH−) Tetrabutylammonium hydroxide was added to the solution of 1 in CH3CN to investigate the above process. Changes in fluorescence emission of 1 upon addition of F− and OH− in CH3CN were almost the same

Mitomycins syntheses: a recent update

• Jean-Christophe Andrez

Beilstein J. Org. Chem. 2009, 5, No. 33, doi:10.3762/bjoc.5.33

Controlling hazardous chemicals in microreactors: Synthesis with iodine azide

• Johan C. Brandt and
• Thomas Wirth

Beilstein J. Org. Chem. 2009, 5, No. 30, doi:10.3762/bjoc.5.30

• tetrabutylammonium hydroxide and sodium azide in water and dichloromethane did not lead to dry, crystalline material [23]. Unfortunately also the procedure using tetrabutylammonium chloride and sodium azide produced a product highly contaminated with DMF, which was not removable without decomposition of the product

• (30 mL). Then tetrabutylammonium hydroxide (100 mmol, 26 g) was added and the mixture was stirred at room temperature for 90 min. Dichloromethane (50 mL) was added and stirring was continued for 10 min. The organic layer was separated and dried over magnesium sulfate. Finally the solvent was removed