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

• acid polymer termini from the initiation were observed, and apparently only syntheses of polymers with a low molar mass could be achieved. In addition, the specific equipment necessary for supercritical CO2 applications will limit its widespread use. Dihydrolevoglucosenone (DLG) is a dipolar aprotic

Metal-free glycosylation with glycosyl fluorides in liquid SO₂

• Krista Gulbe,
• Jevgeņija Lugiņina,
• Edijs Jansons,
• Artis Kinens and
• Māris Turks

Beilstein J. Org. Chem. 2021, 17, 964–976, doi:10.3762/bjoc.17.78

• . reported a ″green″ glycosylation procedure by employing supercritical CO2 (scCO2) as a weakly Lewis acidic reaction medium [37]. The method was successfully applied for the synthesis of O-glycosides from disarmed glycosyl chlorides and bromides in the absence of additional promoter. Herein we disclose a

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

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

• Rodrigo Costa e Silva,
• Luely Oliveira da Silva,
• Aloisio de Andrade Bartolomeu,
• Timothy John Brocksom and
• Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

• . This work is crucial for the success of the subsequent industrial process introduced by the pharmaceutical company Sanofi [80]. After this seminal publication, a consortium between Sanofi and UK/China universities also reported a green protocol for artemisinin synthesis using supercritical CO2 as a

• . Synthesis of artemisinin using TPP and supercritical CO2. Synthesis of artemisinin using chlorophyll a. Quercitol stereoisomer preparation. Photocatalyzed preparation of naphthoquinones. Continuous endoperoxidation of conjugated dienes and subsequent rearrangements leading to oxidized products. The Opatz

Palladium-catalyzed Sonogashira coupling reactions in γ-valerolactone-based ionic liquids

• László Orha,
• József M. Tukacs,
• László Kollár and
• László T. Mika

Beilstein J. Org. Chem. 2019, 15, 2907–2913, doi:10.3762/bjoc.15.284

• into Class 2, of which applications should be strictly limited, particularly in pharmaceutical industry. To develop an environmentally benign alternative of this useful method, the reaction has been extended to green solvents such as water [16], fluorous solvents [17], supercritical CO2 [18], and very

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

• Silvie Rimpelová,
• Michal Jurášek,
• Lucie Peterková,
• Jiří Bejček,
• Vojtěch Spiwok,
• Miloš Majdl,
• Michal Jirásko,
• Miloš Buděšínský,
• Juraj Harmatha,
• Eva Kmoníčková,
• Pavel Drašar and
• Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

• archangelica Wulfen using supercritical CO2 extraction. We show that dansyl-archangelolide localizes in the endoplasmic reticulum of living cells similarly to trilobolide; localization in mitochondria was also detected. This led us to a more detailed study of the anticancer potential of archangelolide

• [12] was described, we aimed to develop a facile method for the isolation of these SLs from the seeds of Laserpitium archangelica Wulfen using supercritical CO2 extraction (SCE; for advantages of this method, see Supporting Information File 1, section 8). In our experience, any part of the plant may

• supercritical CO2 extraction, which was carried out under pressure of 40 MPa at 40 °C until the extract substances passed from the extracted material (when several subsequent fractions were not adding any addition to the weight to the extract). The obtained yellowish extract (42.5 g) was stored in fridge for a

[3 + 2]-Cycloaddition reaction of sydnones with alkynes

• Veronika Hladíková,
• Jiří Váňa and
• Jiří Hanusek

Beilstein J. Org. Chem. 2018, 14, 1317–1348, doi:10.3762/bjoc.14.113

• -selectivity study of the cycloaddition of 3-phenylsydnone with methyl propiolate was undertaken by McGowin et al. [93] in supercritical CO2. At 7.6 MPa they found a linear dependence between the natural logarithm of selectivity (defined as the 3-/4-isomer ratio) and the reaction temperature. In accordance

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• phthalocyanines. TFEO-Pc is soluble not only in general organic solvents but also in liquid carbon dioxide (CO2) and supercritical CO2 [55]. These forms of CO2 have attracted attention as solvents which do not discharge volatile organic compounds (VOCs), and are expected to replace organic solvents as a

• sparingly soluble, (++) means very high solubility, and (±) means moderate solubility. After conducting solubility studies on various phthalocyanines, only phthalocyanine in which all positions were substituted with trifluoroethoxy groups showed high solubility in both liquid CO2 and supercritical CO2. On

• . Solubility of phthalocyanines in liquid CO2 and supercritical CO2. Comparison of IC50 values with laser PDT among phthalocyanine conjugated with cyclodextrin against B16-F10. Characteristics of phthalocyanine/P3HT heterojunction organic thin-film solar cells. Comparison of axial ligand substitution

Continuous-flow processes for the catalytic partial hydrogenation reaction of alkynes

• Carmen Moreno-Marrodan,
• Francesca Liguori and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2017, 13, 734–754, doi:10.3762/bjoc.13.73

• −1, Table 1, entries 29, 30) [137]. Lower performances were observed using packed-bed catalysts and conventional support materials [123], an amorphous Pd81Si19 alloy catalyst in supercritical CO2 (76% sel. at 91% conversion, 358 K) [149] or a capillary reactor (i.d. 250 μm) internally coated with Pd

Continuous N-alkylation reactions of amino alcohols using γ-Al₂O₃ and supercritical CO₂: unexpected formation of cyclic ureas and urethanes by reaction with CO₂

• Emilia S. Streng,
• Darren S. Lee,
• Michael W. George and
• Martyn Poliakoff

Beilstein J. Org. Chem. 2017, 13, 329–337, doi:10.3762/bjoc.13.36

• could be synthesised by incorporation of CO2 from the supercritical solvent into the product. Keywords: continuous flow; heterocycle; N-alkylation; self-optimisation; supercritical CO2; Introduction N-alkylated amines are an important motif present in a range of pharmaceutically and industrially

Recent advances in C(sp³)–H bond functionalization via metal–carbene insertions

• Bo Wang,
• Di Qiu,
• Yan Zhang and
• Jianbo Wang

Beilstein J. Org. Chem. 2016, 12, 796–804, doi:10.3762/bjoc.12.78

• . Moreover, the electron-deficient nature of CO2 will prevent its reaction with the highly reactive metal–carbene species, which are electrophilic in nature. In 2011, Pérez, Etienne and Asensio achieved the TpxAg catalyzed C–H insertion of methane in supercritical CO2 (Scheme 9) [39]. The reaction between

Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications

• Tor E. Kristensen

Beilstein J. Org. Chem. 2015, 11, 446–468, doi:10.3762/bjoc.11.51

Cyclodextrin-grafted polymers functionalized with phosphanes: a new tool for aqueous organometallic catalysis

• Jonathan Potier,
• Stéphane Menuel,
• David Mathiron,
• Véronique Bonnet,
• Frédéric Hapiot and
• Eric Monflier

Beilstein J. Org. Chem. 2014, 10, 2642–2648, doi:10.3762/bjoc.10.276

• supercritical CO2, ionic liquids or fluorous phases have been used to immobilize the organometallic catalyst [3][4][5]. Co-solvents, surfactants, amphiphilic phosphanes, molecular receptors, polymers or dispersed particles have also been investigated to favour contacts between the aqueous and the organic

Supercritical carbon dioxide: a solvent like no other

• Jocelyn Peach and
• Julian Eastoe

Beilstein J. Org. Chem. 2014, 10, 1878–1895, doi:10.3762/bjoc.10.196

• of polar and ionic species and attempts to enhance scCO2 viscosity. Keywords: CO2 chemistry; microemulsion; self-assembly; supercritical CO2; surfactant; viscosity; Introduction In this day and age, sustainability and renewability are watchwords. This includes focus within the scientific community

• being readily available, cheap, non-flammable, recyclable and unrestricted by the US Environmental Protection Agency (EPA) [3][5][6][7][8][9][10][11][12][13][14][15], supercritical CO2 (scCO2) is non-toxic so could potentially be used for the production of consumable products, such as pharmaceutical and

• of surfactants are discussed throughout this review; the structures of which are displayed in Table 1. Fluorocarbon-based surfactants have been used frequently in the field due to the high solubility of fluorocarbon chains in liquid and supercritical CO2. They were first introduced by Hoefling, Enick

Coupled chemo(enzymatic) reactions in continuous flow

• Ruslan Yuryev,
• Simon Strompen and
• Andreas Liese

Beilstein J. Org. Chem. 2011, 7, 1449–1467, doi:10.3762/bjoc.7.169

• lipase in the presence of the acidic chemocatalysts and for reduction of zeolite-catalyzed side reactions [30][31]. The substrates and supercritical CO2 were fed continuously, thus omitting the use of organic solvents for product extraction. An enantiomeric excess of 97% was achieved for the product (R

• resolution of (rac)-1-phenylethanol (22) in supercritical CO2 in a packed-bed reactor loaded with acidic zeolite (A) and Novozym 435 (E) [30]. Synthesis of D-xylulose (28) from D,L-serine (26) and D,L-glyceraldehyde (25) in a continuously operated enzyme membrane reactor. E1: D-Amino acid oxidase; E2

Functionalized copolyimide membranes for the separation of gaseous and liquid mixtures

• Nadine Schmeling,
• Roman Konietzny,
• Daniel Sieffert,
• Patrick Rölling and
• Claudia Staudt

Beilstein J. Org. Chem. 2010, 6, 789–800, doi:10.3762/bjoc.6.86

• area of natural gas treatment a number of different applications are of great interest. In tertiary oil production supercritical CO2 is introduced into the oil field, especially if the oil is distributed in porous layers. As shown in Figure 13, the stream coming out of the oil field then contains the