Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system

• David Liese,
• Hans Henning Wenk,
• Xin Lu,
• Jochen Kleinen and
• Gebhard Haberhauer

Beilstein J. Org. Chem. 2020, 16, 2820–2830, doi:10.3762/bjoc.16.232

• ingredients in a lot of technical applications. They can act as a flotation agent in the enrichment of ores [1], emulsifier and stabilizer for emulsions [2], or as additives for self-cleaning surfaces (artificial lotus effect) [3][4]. Rhamnolipids (RL, Figure 1) are biosurfactants, that are produced by

• described by Leisinger et al. [9]. Rhamnolipids possess some advantages, that make them interesting candidates as cleaning agents or additives for care applications in the consumer goods industry. They can be produced in a fermentation process from renewable nontropic material [10][11]. RL are also

Asymmetric Mannich reactions of (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophiles

• Ziyi Li,
• Li Wang,
• Yunqi Huang,
• Haibo Mei,
• Hiroyuki Konno,
• Hiroki Moriwaki,
• Vadim A. Soloshonok and
• Jianlin Han

Beilstein J. Org. Chem. 2020, 16, 2671–2678, doi:10.3762/bjoc.16.217

• the completion of this transformation (Table 1, entries 11 and 12). Finally, we found that the use of Lewis acids BF3·Et2O and Ti(OiPr)4 as additives for this reaction was unsuccessful and the same level of chemical yield and diastereoselectivity was observed (Table 1, entries 13 and 14). With the

Particle size effect in the mechanically assisted synthesis of β-cyclodextrin mesitylene sulfonate

• Stéphane Menuel,
• Sébastien Saitzek,
• Eric Monflier and
• Frédéric Hapiot

Beilstein J. Org. Chem. 2020, 16, 2598–2606, doi:10.3762/bjoc.16.211

• bioavailability [11][12][13]. In our previous studies, CDs acted either as reactants [14][15], or as additives [16][17], and were shown to display supramolecular interactions with the other reaction partners. We demonstrated that the formation of CD/substrate supramolecular complexes favored the dispersion of the

Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol

• Ekaterina E. Stepanova,
• Maksim V. Dmitriev and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2020, 16, 2322–2331, doi:10.3762/bjoc.16.193

• acids or their esters IV with o-aminothiophenol (1a) to afford the target BTAs III can be explained both by the impossibility of thioesterification/thiotransesterification to proceed under additives-free conditions and by the high nucleophilicity of the o-aminothiophenol’s SH group that attacked the

• additives for carbodiimide coupling reactions, DMAP [30] and HOBt [31]. The utilization of HOBt (Table 1, entries 25 and 26) in acetonitrile as an additive did not significantly influence the yield of BTA 3a. But since the solubility of HOBt in acetonitrile is poor [32], we examined the reaction in DMF and

Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones

• Viktor M. Tkachuk,
• Oleh O. Lukianov,
• Mykhailo V. Vovk,
• Isabelle Gillaizeau and
• Volodymyr A. Sukach

Beilstein J. Org. Chem. 2020, 16, 2304–2313, doi:10.3762/bjoc.16.191

• acid (2a). Effect of boric acid and pyridine additives on the Chan–Evans–Lam reaction of 4-trifluoromethylpyrimidin-2(1H)-one (1а) with phenylboronic acid pinacol ester (6а). Supporting Information Supporting Information File 468: Experimental procedures, characterization data, copies of the 1H and

Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups

• Xiaoyun Hu,
• Jianxin Guo,
• Cui Wang,
• Rui Zhang and
• Victor Borovkov

Beilstein J. Org. Chem. 2020, 16, 1875–1880, doi:10.3762/bjoc.16.155

• solvent screening showed that the target product could be obtained in 95% ee catalyzed by 3 in CHCl3 (Table 1, entry 4). However, acidic and basic additives [23][24] resulted in a decrease of the enantioselectivity (Table 1, entries 10–12), or even to racemization in the case of TFA (Table 1, entry 13

• explains that more polar or protic solvents and strong acidic additives also destroyed the H-bondings resulting in decreased enantioselectivities or even racemization (Table 1, entries 7 and 13). Conclusion In summary, a new phosphoric acid bearing two free hydroxy groups was synthesized based on a highly

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway

• Esra Demir,
• Ozlem Sari,
• Yasin Çetinkaya,
• Ufuk Atmaca,
• Safiye Sağ Erdem and
• Murat Çelik

Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148

• phenyl, benzyl and fused cyclic alkyl groups in different solvents under mild reaction conditions without additives and catalysts was studied. Oxazolidinones and five-membered cyclic carbonates were obtained in ratios close to 1:1 in the cyclization reactions. The best yields of these compounds were

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

• Lucas Guillemard and
• Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

• oxidants and/or additives. In order to provide a solution towards these limitations of the undirected C–H activation, the group of Lee initiated a project merging gold-catalyzed C–H activation with photoredox catalysis (Figure 42) [104]. Such a dual catalytic system should promote the desired C–C bond

One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?

• Isaline Bonnin,
• Raphaël Mereau,
• Thierry Tassaing and
• Karine De Oliveira Vigier

Beilstein J. Org. Chem. 2020, 16, 1713–1721, doi:10.3762/bjoc.16.143

• to sorbitol and 3) dehydration of sorbitol to isosorbide (Scheme 1). Isosorbide, a molecule obtained from biomass can find many applications such as additives, pharmaceuticals [2][3] and monomers for polymer industries [4][5][6]. For instance, one polymer obtained from isosorbide, poly(ethylene-co

Pauson–Khand reaction of fluorinated compounds

• Jorge Escorihuela,
• Daniel M. Sedgwick,
• Alberto Llobat,
• Mercedes Medio-Simón,
• Pablo Barrio and
• Santos Fustero

Beilstein J. Org. Chem. 2020, 16, 1662–1682, doi:10.3762/bjoc.16.138

• , mild oxidizing additives such as amine oxides, aminophosphines, phosphine oxides, and sulfoxides may be used as promoters to facilitate the dissociation step, by oxidatively removing one of the CO ligands in form of CO2 [40]. The most common oxidants are N-morpholine N-oxide (NMO), trimethylamine N

Photoredox-catalyzed silyldifluoromethylation of silyl enol ethers

• Vyacheslav I. Supranovich,
• Vitalij V. Levin and
• Alexander D. Dilman

Beilstein J. Org. Chem. 2020, 16, 1550–1553, doi:10.3762/bjoc.16.126

• starting enol ether. Moreover, a further increase in reaction time was accompanied by a decrease in the product yield. Finally, GC monitoring suggested complete consumption of the silyl enol ether within 6 hours. It should also be pointed out that the addition of basic additives, which are frequently

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

The McKenna reaction – avoiding side reactions in phosphonate deprotection

• Katarzyna Justyna,
• Joanna Małolepsza,
• Damian Kusy,
• Waldemar Maniukiewicz and
• Katarzyna M. Błażewska

Beilstein J. Org. Chem. 2020, 16, 1436–1446, doi:10.3762/bjoc.16.119

• step of the McKenna reaction. To this end, we used model compounds from our previous work, analyzed the possible side reactions, and proposed solutions in order to minimize or prevent the unwanted processes. We also showed that tertiary amines, that are commonly used as additives to prevent these side

• demonstrated that contrary to common belief: 1) BTMS itself led to the cleavage of tert-butyl carboxyesters, and 2) amines, a commonly used standard additives in the McKenna reaction were not generally safe and may promoted side reactions in the presence of certain functional groups. Besides that, we

Synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1-a]isoquinolines via three-component [3 + 2] cycloaddition followed by one-pot N-allylation and intramolecular Heck reactions

• Xiaoming Ma,
• Suzhi Meng,
• Xiaofeng Zhang,
• Qiang Zhang,
• Shenghu Yan,
• Yue Zhang and
• Wei Zhang

Beilstein J. Org. Chem. 2020, 16, 1225–1233, doi:10.3762/bjoc.16.106

• evaporating unreacted 3-bromopropene (7) from the reaction mixture, crude product 8a was used for developing the intramolecular Heck reaction by screening Pd(II) catalysts, ligands, bases, additives, solvents, temperatures and reaction time (Table 1). The initial intramolecular Heck reactions were carried out

Activated carbon as catalyst support: precursors, preparation, modification and characterization

• Melanie Iwanow,
• Tobias Gärtner,
• Volker Sieber and
• Burkhard König

Beilstein J. Org. Chem. 2020, 16, 1188–1202, doi:10.3762/bjoc.16.104

• necessary to eliminate a high amount of internal carbon for the formation of a well-developed and highly porous carbon structure [6]. In general, the physical activation of carbon materials has the advantage over chemical activation to avoid impurities or additives in the final materials from the

Bipyrrole boomerangs via Pd-mediated tandem cyclization–oxygenation. Controlling reaction selectivity and electronic properties

• Liliia Moshniaha,
• Marika Żyła-Karwowska,
• Joanna Cybińska,
• Piotr J. Chmielewski,
• Ludovic Favereau and
• Marcin Stępień

Beilstein J. Org. Chem. 2020, 16, 895–903, doi:10.3762/bjoc.16.81

• and increasing curvature of the bipyrrole linkage. The efficiency of the oxygenation step is dependent on a several of factors, i.e., Pd loading, concentration, and additives. The isolation of unoxygenated products cNMI2H and cNMI3H emphasizes the role of acceptor units and decreased inter-pyrrole

Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations

• Laura Sršan and
• Thomas Ziegler

Beilstein J. Org. Chem. 2020, 16, 888–894, doi:10.3762/bjoc.16.80

• coupling reagents, such as benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) or diisopropyl carbodiimide (DIC) and additives, such as 1-hydroxybenzotriazole (HOBt) or triethylphosphine. [29][30][31] However, in our hands, none of the described methods reached the high yields that

Aldehydes as powerful initiators for photochemical transformations

• Maria A. Theodoropoulou,
• Nikolaos F. Nikitas and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2020, 16, 833–857, doi:10.3762/bjoc.16.76

• state quencher, as well as by the lowered rate of the reaction in the presence of the triplet energy quencher 2,5-dimethylhexa-2,4-diene or pyridazines, additives with lower triplet state energies than 4-anisaldehyde (52). The fact that the solvent polarity did not affect the sensitivity of the process

Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid

• Dong Cai,
• ZhiHua Zhang,
• Yufan Meng,
• KaiLi Zhu,
• LiYi Chen,
• ChangXiang Yu,
• ChangWei Yu,
• ZiYi Fu,
• DianShen Yang and
• YiXia Gong

Beilstein J. Org. Chem. 2020, 16, 798–808, doi:10.3762/bjoc.16.73

• with 1-Boc-piperazine (2.5 equiv) without any other additives can readily proceed in acetonitrile at reflux temperature in 95% yield. Having demonstrated the effectiveness of the new procedure, we decided to apply this method towards the synthesis of compound 10. But our investigations proved that the

Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties

• Takahide Shimada,
• Shigeki Mori,
• Masatoshi Ishida and
• Hiroyuki Furuta

Beilstein J. Org. Chem. 2020, 16, 587–595, doi:10.3762/bjoc.16.53

• as gold catalysts (e.g., gold(I) cyanide), solvents (e.g., CH2Cl2, THF, MeCN, DMF), additives (e.g., TFA, Sc(OTf)3), and temperature, the reaction conditions as mentioned earlier were chosen for the synthesis of 5a and 6a (Table S1, Supporting Information File 1). Because of the electron-deficient

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

• Pezhman Shiri and
• Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

Aerobic synthesis of N-sulfonylamidines mediated by N-heterocyclic carbene copper(I) catalysts

• Faïma Lazreg,
• Marie Vasseur,
• Alexandra M. Z. Slawin and
• Catherine S. J. Cazin

Beilstein J. Org. Chem. 2020, 16, 482–491, doi:10.3762/bjoc.16.43

• between alkyne, sulfonyl azide and amine/alcohol was described as a synthetic route to generate sulfonyltriazole intermediates. However, the presence of additives and high catalyst loading (CuI 10 mol %) were required for the synthesis of N-sulfonylimidates (Scheme 1, left). Over the last two decades

Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt

• Tobias Lucas,
• Jule-Philipp Dietz and
• Till Opatz

Beilstein J. Org. Chem. 2020, 16, 445–450, doi:10.3762/bjoc.16.41

• . The hydrochlorides furnished the highest yields and no undesired byproducts were formed. In contrast to the related reaction with guanidinium salts [36], the reactions with amidine hydrochlorides did not require any basic additives. Under these improved conditions, the scope of the reaction for

Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

• Vuyisa Mzozoyana,
• Fanie R. van Heerden and
• Craig Grimmer

Beilstein J. Org. Chem. 2020, 16, 190–199, doi:10.3762/bjoc.16.22

• coumarins have been identified from natural sources [1][2]. Coumarins have been reported to play a vital role as food and cosmetics constituents, cigarette additives, and dye-sensitized solar cells [3][4]. In addition, coumarins possess some biological activities such as anti-inflammatory [5], antitumor [6

Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst

• Abhijit Paul,
• Debnath Chatterjee,
• Srirupa Banerjee and
• Somnath Yadav

Beilstein J. Org. Chem. 2020, 16, 140–148, doi:10.3762/bjoc.16.16

• observed. To further test the functional group tolerance of the reaction, we employed a modified version of the “robustness screen” method promulgated by Glorius and co-workers [50][51][52]. For this purpose, the reaction of indole (1a) was carried out with 2b in the presence of several additives bearing