Inductive heating and flow chemistry – a perfect synergy of emerging enabling technologies

• Conrad Kuhwald,
• Sibel Türkhan and
• Andreas Kirschning

Beilstein J. Org. Chem. 2022, 18, 688–706, doi:10.3762/bjoc.18.70

• catalysis can be generated directly by the functionalized nanostructured particles (Scheme 12, case C) [50]. This was achieved by reductive precipitation of Pd(0) nanoparticles from ammonium-bound tetrachloropalladate [84][85], which showed good catalytic activity in various cross-coupling reactions under

Trichloroacetic acid fueled practical amine purifications

• Aleena Thomas,
• Baptiste Gasch,
• Enzo Olivieri and
• Adrien Quintard

Beilstein J. Org. Chem. 2022, 18, 225–231, doi:10.3762/bjoc.18.26

• . Inspired by recent work on out of equilibrium molecular machinery, using trichloroacetic acid (TCA), we disclose a purification technique considerably decreasing the number of operations and the waste generation required for such purifications. At first, TCA triggers the precipitation of the amines through

• from rotaxanes, cucurbit[8]uril, to supramolecular smart materials [11][12][13][14][15][16]. TCA is also known for its application in the precipitation of proteins through what is believed to be an unfolding of the proteins structures [17][18]. In this context, we hypothesized that TCA could be used to

• this mixture dissolved in EtOAc, precipitation of the amine salt enabled the removal of naphthalene in the solvent. Beside the choice of the solvent for the crystallization which strongly depends on the solubility of the protonated amine salts involved, we first focused on the optimization of the

Stepwise PEG synthesis featuring deprotection and coupling in one pot

• Logan Mikesell,
• Dhananjani N. A. M. Eriyagama,
• Yipeng Yin,
• Bao-Yuan Lu and
• Shiyue Fang

Beilstein J. Org. Chem. 2021, 17, 2976–2982, doi:10.3762/bjoc.17.207

• reaction, which mainly include styrene and p-toluenesulfonic acid. As a result, when the reaction is performed at large scales, there is a high probability that the product can be purified by methods such as partition, precipitation and crystallization. The major advantage of using a base-labile protecting

Study on the interactions between melamine-cored Schiff bases with cucurbit[n]urils of different sizes and its application in detecting silver ions

• Jun-Xian Gou,
• Yang Luo,
• Xi-Nan Yang,
• Wei Zhang,
• Ji-Hong Lu,
• Zhu Tao and
• Xin Xiao

Beilstein J. Org. Chem. 2021, 17, 2950–2958, doi:10.3762/bjoc.17.204

• addition, the UV–vis spectrum in Figure 4a shows that the absorbance of TBT keeps on the decrease (ΔA = 0.623) without red shift or blue shift in the presence of Q[8]. Both of the above phenomena show that Q[8] interacted with the “arm” of TBT and produced precipitation due to aggregation, which is also

Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

• Azra Kocaarslan,
• Zafer Eroglu,
• Önder Metin and
• Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

• alumina column. Excess amount of THF was evaporated by a rotary evaporator. After precipitation of the mixture to cold methanol, the polymer was collected by filtration and dried under vacuum overnight. 1H NMR was demonstrated in Figure 4. Synthesis of polystyrene-b-poly(ε-caprolactone) (PS-b-PCL) Firstly

• rotary evaporator. After precipitation of the mixture to cold methanol, the polymer was collected by filtration and dried under vacuum overnight. Mn,GPC: 3510 g·mol−1, Mw/Mn: 1.10. Synthesis of cross-linked polymer Az-3 and Alk-5 was mixed in equal ratio (1 equiv) with CuIICl2 (0.05 equiv) and PMDETA

A visible-light-induced, metal-free bis-arylation of 2,5-dichlorobenzoquinone

• Pieterjan Winant and
• Wim Dehaen

Beilstein J. Org. Chem. 2021, 17, 2315–2320, doi:10.3762/bjoc.17.149

• be a crucial discovery in the optimization process, since using methanol as a reaction solvent not only significantly simplified purification, but also increased the yield (Table 1, entry 4). Precipitation also occurred in acetonitrile, however, the yield was slightly lower (Table 1, entry 5). While

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• and produce long and uniform polysaccharides. Solvent systems like DMAc/LiCl or quaternary ammonium electrolytes are able to dissolve cellulose and could overcome the precipitation issues during synthesis [55][56]; however, these systems are not always compatible with reaction conditions [57]. The

• yields (2–5%). This approach circumvented the precipitation of the water-insoluble oligomers and allowed for chain elongation [72][73]. This methodology was improved employing a protic co-catalyst system to yield DP > 120 in a 26% conversion [74]. Generally, an acid catalyst would promote the hydrolysis

• pattern by chemical synthesis, albeit in low yields. Selective disruption of intra- and intermolecular hydrogen bonds suggested that modifications can be designed to prevent precipitation and guide cellulose assembly. Xyloglucans Xyloglucans (XGs) are based on a β(1–4)-Glc backbone decorated with

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Nitroalkene reduction in deep eutectic solvents promoted by BH₃NH₃

• Chiara Faverio,
• Monica Fiorenza Boselli,
• Patricia Camarero Gonzalez,
• Alessandra Puglisi and
• Maurizio Benaglia

Beilstein J. Org. Chem. 2021, 17, 1041–1047, doi:10.3762/bjoc.17.83

• physicochemical properties can be easily tuned and designed to meet specific requirements; they also offer the possibility to develop convenient methodologies to isolate the product by extraction or precipitation, and thus making the reuse of the DES mixture feasible. The large number of biodegradable raw

A chromatography-free and aqueous waste-free process for thioamide preparation with Lawesson’s reagent

• Ke Wu,
• Yichen Ling,
• An Ding,
• Liqun Jin,
• Nan Sun,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2021, 17, 805–812, doi:10.3762/bjoc.17.69

• added and the resulting solution was gradually cooled. The precipitation was observed at 65 °C and stirring was continued until the temperature reached 20 °C. After filtration, the solid was washed with heptane (50 mL) and dried to afford 36.0 g of the desired thioamide product 2e (79%) as bright yellow

Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents

• Anuj Kumar Chhalodia and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 569–580, doi:10.3762/bjoc.17.51

• precipitation of the catalyst. The catalyst was filtered off, the filtrate was dried with MgSO4 and concentrated in vacuo to give pure 27 (0.34 g, 2.05 mmol, 82%) as colorless solid. TLC Rf 0.17 (cyclohexane/EtOAc 1:1); IR (diamond-ATR) ν̃: 3014 (w), 2948 (w), 2932 (w), 1762 (m), 1687 (w), 1442 (w), 1433 (w

Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines

• Wilfred J. M. Lewis,
• David M. Shaw and
• Jeremy Robertson

Beilstein J. Org. Chem. 2021, 17, 334–342, doi:10.3762/bjoc.17.31

• separate large-scale experiment [from crude 16 (17.6 g, 69.8 mmol) giving hydrochloride 17 (13.1 g, 69.4 mmol)]. Thus, a 6.4 g sample of the crude salt 17 was dissolved in methanol/triethylamine 9:1, concentrated, then re-dissolved in the minimum amount of methanol to allow precipitation of triethylamine

Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols

• Armin Ariamajd,
• Nils J. Gerwien,
• Benjamin Schwabe,
• Stefan Dix and
• Matthew N. Hopkinson

Beilstein J. Org. Chem. 2021, 17, 83–88, doi:10.3762/bjoc.17.8

• observed within 16 h at rt, and the heteroaromatic compounds 1a–e could be isolated in good yields. Subsequent N-methylation with methyl trifluoromethanesulfonate in CH2Cl2 also proceeded smoothly with the BT-SRF reagents each being obtained after 48 h at rt in high yields upon precipitation with Et2O. As

Semiautomated glycoproteomics data analysis workflow for maximized glycopeptide identification and reliable quantification

• Steffen Lippold,
• Arnoud H. de Ru,
• Jan Nouta,
• Peter A. van Veelen,
• Magnus Palmblad,
• Manfred Wuhrer and
• Noortje de Haan

Beilstein J. Org. Chem. 2020, 16, 3038–3051, doi:10.3762/bjoc.16.253

• File 2) but may occur at the peptide portion as well [24][25][26]. Formylation is likely introduced by the exposure of the tryptic peptides to formic acid during the acid precipitation of sodium deoxycholate in the final step of the sample preparation and during subsequent storage [24]. Within the

• to room temperature. Tryptic digestion was started by the addition of 50 µL digestion buffer containing 50 mM ammonium bicarbonate pH 8.5 and 200 ng sequencing-grade trypsin. Upon mixing for 5 min, the sample was incubated at 37 °C overnight. Acid precipitation using 1.2 µL formic acid was performed

Secondary metabolites of Bacillus subtilis impact the assembly of soil-derived semisynthetic bacterial communities

• Heiko T. Kiesewalter,
• Carlos N. Lozano-Andrade,
• Mikael L. Strube and
• Ákos T. Kovács

Beilstein J. Org. Chem. 2020, 16, 2983–2998, doi:10.3762/bjoc.16.248

• place [11]. The composition of microbial communities depends on multiple factors. Studies have revealed that the composition of bacterial soil communities varies at the same sampling site during different seasons [12][13]. Moreover, it has been recently demonstrated that precipitation rates have a

Optical detection of di- and triphosphate anions with mixed monolayer-protected gold nanoparticles containing zinc(II)–dipicolylamine complexes

• Lena Reinke,
• Julia Bartl,
• Marcus Koch and
• Stefan Kubik

Beilstein J. Org. Chem. 2020, 16, 2687–2700, doi:10.3762/bjoc.16.219

• water/methanol 1:2 (v/v). These anions caused the bright red solutions of the nanoparticles to change their color because of nanoparticle aggregation followed by precipitation, whereas halides or oxoanions such as sulfate, nitrate, or carbonate produced no effect. The sensitivity of phosphate sensing

• . Hydrogenphosphate induced a nanoparticle precipitation only at a concentration of ca. 400 μmol/L, at which the precipitates formed in the presence of diphosphates and triphosphates redissolved. A nanoparticle containing fewer binding sites was more sensitive, while increasing the relative number of zinc(II

• formed, the solutions either lose their color because of nanoparticle precipitation or they adopt a different color. Dispersed spherical AuNPs with a diameter of ca. 10 nm lead to intensely colored red solutions, for example, which turn purple or blue upon nanoparticle aggregation because the localized

NMR Spectroscopy of supramolecular chemistry on protein surfaces

• Peter Bayer,
• Anja Matena and
• Christine Beuck

Beilstein J. Org. Chem. 2020, 16, 2505–2522, doi:10.3762/bjoc.16.203

• ligands as well, thus altering their electrostatic interactions. Around the isoelectric point, where a molecule is neutral, hydrophobic interactions become more pronounced, which can lead to formation of soluble aggregates or even precipitation. Co-solvents such as DMSO-d6 are popular as solvents for more

Naphthalene diimide bis-guanidinio-carbonyl-pyrrole as a pH-switchable threading DNA intercalator

• Poulami Jana,
• Filip Šupljika,
• Carsten Schmuck and
• Ivo Piantanida

Beilstein J. Org. Chem. 2020, 16, 2201–2211, doi:10.3762/bjoc.16.185

• and 115 nm at ratios of r = 0.1 and 0.5, respectively. Higher ratios resulted in even larger particle size, which eventually ended in precipitation. Conclusion We designed and synthesized a novel naphtalene diimide analogue equipped at imide positions with two guanidinio-carbonyl-pyrrole (GCP) pendant

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

• Shahboz Yakubov and
• Joshua P. Barham

Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183

• precipitation in MeCN, and the fluorination with F2 in the presence of sodium tetrafluoroborate affords Selectfluor®. Moreover, by variation of these conditions, different derivatives of Selectfluor® (e.g., a methyl derivative: Selectfluor® II and a 2,2,2-trifluoroethyl derivative) with different physical

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

• Paola Vitale,
• Luciana Cicco,
• Ilaria Cellamare,
• Filippo M. Perna,
• Antonio Salomone and
• Vito Capriati

Beilstein J. Org. Chem. 2020, 16, 1915–1923, doi:10.3762/bjoc.16.158

• reaction mixture and washed with a few drops of EtOAc or Et2O. The solution was extracted with EtOAc (3 × 10 mL). The combined organic phases were dried over anhydrous Na2SO4 and the solvent was concentrated in vacuo. The addition of Et2O to the crude mixture allowed the further precipitation of 3a, which

Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells

• Giacomo Mari,
• Lucia De Crescentini,
• Serena Benedetti,
• Francesco Palma,
• Stefania Santeusanio and
• Fabio Mantellini

Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133

• their antiproliferative activity directly by precipitation from the reaction medium, avoiding any possible and common subsequent side reactions for this substrate during the purification processes (Scheme 1). On the other hand, also the fully reduced form of BER, namely tetrahydroberberine (THBER) or

• detectable only in traces (Table 1, entries 1–5). The monitoring by TLC of the reaction conducted in acetonitrile reveals the formation of derivative 2a, which, however, does not precipitate in the reaction medium (Table 1, entry 6). The spontaneous precipitation is particularly relevant to prevent any

• direct precipitation. The mono- and two-dimensional NMR studies confirm that hydrazono-DHBER 2a–n are in the iminium-tautomeric form. For example, the COSY experiment of hydrazono-DHBER 2a clearly indicates the presence of three sets of related signals: the system with the triplet at 5.24 ppm

Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides

• Mateo Berton,
• Kevin Sheehan,
• Andrea Adamo and
• D. Tyler McQuade

Beilstein J. Org. Chem. 2020, 16, 1343–1356, doi:10.3762/bjoc.16.115

• batch version, which usually takes 24 h at room temperature [47][67]. The reaction was carried out by flowing iPrCl/TMPH, 1.2:1 dissolved in THF/toluene, 1:1 at a 0.5 mL/min flow rate and 80 °C. As a drawback, we observed LiCl precipitation in the flask ≈2 h after collection. A clear solution can be

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