Sustainable tandem acylation/Diels–Alder reaction toward versatile tricyclic epoxyisoindole-7-carboxylic acids in renewable green solvents

• Ayhan Yıldırım

Beilstein J. Org. Chem. 2024, 20, 1308–1319, doi:10.3762/bjoc.20.114

• ][34][35][36][37][38]. In addition to their unique properties, vegetable oils are known to be useful as green solvents in many applications [39][40][41][42]. The evaluation of vegetable oils as alternative solvents in organic synthesis is very limited [43][44][45][46][47]. Synthetic chemists are still

• + 2] annulation reactions [68][69][70]. This study was the first to evaluate the performances of sunflower seed oil (SSO), olive oil (OO), oleic acid (OA) and lauryl myristate (LM) as green solvents in the well-known intramolecular Diels–Alder furan (IMDAF) reaction between aminofuranes and maleic

• , which are readily available from a large number and variety of natural sources around the world, fatty acids and wax esters, can be excellent alternative reaction media to existing conventional and green solvents for IMDAF reactions. This study reveals the first utilization of these materials as

A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics

• Kathryn M. Wolfe,
• Shahidul Alam,
• Eva German,
• Fahad N. Alduayji,
• Maryam Alqurashi,
• Frédéric Laquai and
• Gregory C. Welch

Beilstein J. Org. Chem. 2023, 19, 1620–1629, doi:10.3762/bjoc.19.119

• devices at low cost with minimal environmental impact becomes viable, especially if processed from green solvents [3][4][5]. These devices have the opportunity to be integrated into buildings, automobiles, Internet of Things (IoT) devices, etc. This has motivated scientists to develop OPV technology over

• -PDIN-H scaffold was functionalized with a benzyl (CN-PDIN-B) or pentafluorobenzyl group (CN-PDIN-FB). Addition of the benzyl and pentafluorobenzyl groups was to enhance solubility in green solvents, while nitrile functionalization was done to further stabilize the LUMO of the compounds. These materials

• with any traditional transport layer and are applicable for a wide range of high-efficiency OPVs. Furthermore, the CILs processed from ethyl acetate can be applied to fabricating fully environmentally friendly OPVs based on eco-friendly or green solvents, especially for indoor applications. a) Select

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

• Stéphanie Hesse

Beilstein J. Org. Chem. 2023, 19, 1537–1544, doi:10.3762/bjoc.19.110

• promising emerging class of green solvents as they offer numerous advantages, such as low volatility, non-flammability, chemical and thermal stability, recyclability, and above all a good biodegradability [10]. Moreover, their synthesis is usually easy and cheap as DES are formed by simply mixing an H-bond

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

• ]. Therefore, choosing environmentally benign solvents becomes ever more relevant [27]. Accordingly, some research groups have been also looking for "green" and safer solvents suitable for CROP of 2-oxazolines. "Green" solvents are considered environmentally friendly, less hazardous solvents that make a

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

• Surendran Amrutha,
• Sankaran Radhika and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

• applied in Sonogashira coupling reactions run in green solvents. The substantial increment of prices for many transition and rare earth metals over the past decade demands more affordable alternatives. This study thus opens the path towards the development of green protocols and application of green

• complex of cobalt and N-heterocyclic ligand supported on carbon nanotubes and pure cobalt nanoparticles was developed [37]. Propargylamine derivatives were synthesized in extremely high yields in green solvents by this catalyst. The catalytic system can be easily recovered and reused 7 times without any

Green synthesis of C5–C6-unsubstituted 1,4-DHP scaffolds using an efficient Ni–chitosan nanocatalyst under ultrasonic conditions

• Soumyadip Basu,
• Sauvik Chatterjee,
• Suman Ray,
• Suvendu Maity,
• Prasanta Ghosh,
• Asim Bhaumik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 133–142, doi:10.3762/bjoc.18.14

• . We mainly focused on the synthesis under green aspects and towards a high product diversity. We initially chose three green solvents with a relatively low boiling point, ethanol, water, and acetone, respectively, as a reaction medium. A series of reactions was examined in these solvents, using an

Asymmetric organocatalyzed synthesis of coumarin derivatives

• Natália M. Moreira,
• Lorena S. R. Martelli and
• Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

• needed to accomplish procedures that allow recycling and lower catalyst loading, intertwined with the use of green solvents, in order to provide efficient and sustainable synthesis of these important pharmacologically active compounds. Coumarin-derived commercially available drugs. Inhibition of

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

• (entries 6 and 8, Table 1). Therefore, DES mixture B (ChCl/gly 1:2) and glycerol were selected as reaction media of choice to further investigate the reduction of nitroalkenes mediated by ammonia borane. Both solvent systems represent promising alternatives, green solvents for organic reactions; glycerol

Ultrasound-assisted Strecker synthesis of novel 2-(hetero)aryl-2-(arylamino)acetonitrile derivatives

• Emese Gal,
• Luiza Gaina,
• Hermina Petkes,
• Alexandra Pop,
• Castelia Cristea,
• Gabriel Barta,
• Dan Cristian Vodnar and
• Luminiţa Silaghi-Dumitrescu

Beilstein J. Org. Chem. 2020, 16, 2929–2936, doi:10.3762/bjoc.16.242

• using “green” solvents, for example, low vapor pressure solvents such as ionic liquids [3], low volatile solvents such as glycerol, ethylene glycol and its oligomers, or nontoxic water solvent, as well as in heterogeneous media under solvent-free conditions [4]. Other advantages induced by sonication

One-pot multicomponent green Hantzsch synthesis of 1,2-dihydropyridine derivatives with antiproliferative activity

• Giovanna Bosica,
• Kaylie Demanuele,
• José M. Padrón and
• Adrián Puerta

Beilstein J. Org. Chem. 2020, 16, 2862–2869, doi:10.3762/bjoc.16.235

• reagents, in the amount of catalyst, and in the temperature as well as the effect of the chosen green solvents (Figure 1). Increasing the temperature did not significantly change the reaction yield or reduce the reaction time, while the presence of a green solvent, such as water or ethanol, negatively

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

• coupling is often unaffected by the choice of solvent, and therefore the Suzuki–Miyaura reaction provides limited information regarding the usefulness of any particular solvent for organic synthesis. Keywords: cross coupling; green solvents; palladium; solvent selection; Suzuki reaction; Findings The

Why do thioureas and squaramides slow down the Ireland–Claisen rearrangement?

• Dominika Krištofíková,
• Juraj Filo,
• Mária Mečiarová and
• Radovan Šebesta

Beilstein J. Org. Chem. 2019, 15, 2948–2957, doi:10.3762/bjoc.15.290

• rearrangements. Furthermore, these organocatalysts slowed down the Ireland–Claisen rearrangement in comparison to an uncatalyzed reaction. The catalyst-free reaction proceeded well in green solvents or without any solvent. DFT calculations showed that the activation barriers are higher for reactions involving

• hydrogen-donating organocatalysts and kinetic experiments suggest that the catalysts bind stronger to the starting silyl ketene acetals than to transition structures thus leading to inefficient rearrangement reactions. Keywords: DFT calculations; green solvents; H-bonding catalysts; Ireland–Claisen

• other solvents, emphasizing green solvents, which have not been evaluated in Ireland–Claisen rearrangements before. 2-Methyltetrahydrofuran (2-MeTHF) is derived from renewable resources and has a higher boiling point (80 °C) and lower heat of vaporization compared to THF. The Ireland–Claisen

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

Safe and highly efficient adaptation of potentially explosive azide chemistry involved in the synthesis of Tamiflu using continuous-flow technology

• Cloudius R. Sagandira and
• Paul Watts

Beilstein J. Org. Chem. 2019, 15, 2577–2589, doi:10.3762/bjoc.15.251

• NaN3, 50 °C and 12 s affording full conversion (HPLC) towards the desired azide 5 in 91% isolated yield. Unlike all literature procedures [9][19][20], side product 5a was not detected using our procedure at 50 °C and 12 s residence time. The use of green solvents, excellent selectivities, safe handling

• full conversion of potentially explosive azide 7 was achieved by using green solvents water and acetonitrile. The reaction temperatures for C-3 azidation (mesyl shikimate 4 azidation, 25 °C, vide supra) differed dramatically with the C-5 azidation (acetamide azidation, 190 °C). This is because the

A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

• Piyali Sarkar,
• Sayan Sarkar and
• Pradyut Ghosh

Beilstein J. Org. Chem. 2019, 15, 1505–1514, doi:10.3762/bjoc.15.152

• environmentally benign solvent water has been used [11]. Organocatalytic nanoreactors have emerged as an exciting area for novel organic syntheses, offering environmentally friendlier processes [13][14][15][16][17][18]. The distinct nanospace around the substrates, use of green solvents and catalyst recycling

Ammonium-tagged ruthenium-based catalysts for olefin metathesis in aqueous media under ultrasound and microwave irradiation

• Łukasz Gułajski,
• Andrzej Tracz,
• Katarzyna Urbaniak,
• Stefan J. Czarnocki,
• Michał Bieniek and
• Tomasz K. Olszewski

Beilstein J. Org. Chem. 2019, 15, 160–166, doi:10.3762/bjoc.15.16

• reactions carried out with the use of green solvents, for which there is currently an increasing demand, especially in industrial practice, as a replacement for those with major regulatory issues such as chlorinated (dichloromethane, 1,2-dichloroethane) or aromatic solvents (toluene, benzene) [13][14][15

An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes

• Hashem Sharghi,
• Pezhman Shiri and
• Mahdi Aberi

Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253

• handling, and even reusability [34]. Ionic liquids (ILs) have been extensively reported as green solvents in organic transformations, owing to their considerable properties such as the ability to dissolve a wide range of substances, very low vapor pressure, high thermal stability, recyclability, non

Heterogeneous acidic catalysts for the tetrahydropyranylation of alcohols and phenols in green ethereal solvents

• Ugo Azzena,
• Massimo Carraro,
• Gloria Modugno,
• Luisa Pisano and
• Luigi Urtis

Beilstein J. Org. Chem. 2018, 14, 1655–1659, doi:10.3762/bjoc.14.141

• Ugo Azzena Massimo Carraro Gloria Modugno Luisa Pisano Luigi Urtis Dipartimento di Chimica e Farmacia, Università degli Studi di Sassari, via Vienna 2, 07100 – Sassari, Italy 10.3762/bjoc.14.141 Abstract The application of heterogeneous catalysis and green solvents to the set up of widely

• one-pot reaction conditions. Keywords: green chemistry; green solvents; heterogeneous catalysts; multistep reactions; tetrahydropyranylation; Introduction Due to their general stability to a wide range of reagents and ease of removal, tetrahydropyranyl (THP) ethers are widely employed in multistep

Halogen-containing thiazole orange analogues – new fluorogenic DNA stains

• Aleksey A. Vasilev,
• Meglena I. Kandinska,
• Stanimir S. Stoyanov,
• Stanislava B. Yordanova,
• David Sucunza,
• Juan J. Vaquero,
• Obis D. Castaño,
• Stanislav Baluschev and
• Silvia E. Angelova

Beilstein J. Org. Chem. 2017, 13, 2902–2914, doi:10.3762/bjoc.13.283

• the samples in the ultrasonic bath and this makes external cooling difficult. In addition, the ultrasound irradiation promotes side reactions and thus leads to slightly lower reaction yields when compared to the room temperature conditions. It is well known that water is one of the most useful green

• solvents in organic synthesis. The reaction in water as a solvent provided moderate yields (procedures B1 and B2), but the subsequent scale-up of these reactions could be favorable on using intermediates with better water solubility. The best reaction yields for TO-7Cl were obtained on using procedure C1

Block copolymers from ionic liquids for the preparation of thin carbonaceous shells

• Sadaf Hanif,
• Bernd Oschmann,
• Dmitri Spetter,
• Muhammad Nawaz Tahir,
• Wolfgang Tremel and
• Rudolf Zentel

Beilstein J. Org. Chem. 2017, 13, 1693–1701, doi:10.3762/bjoc.13.163

• energy is needed to overcome the lattice energy and melt the salt. Ion liquids are also called “green solvents”, because of their low vapor pressure, fire resistance and thermal stability [4]. Beside this, they have a high ionic conductivity, large heat capacity and good thermal and chemical stability [5

An eco-compatible strategy for the diversity-oriented synthesis of macrocycles exploiting carbohydrate-derived building blocks

• Sushil K. Maurya and
• Rohit Rana

Beilstein J. Org. Chem. 2017, 13, 1106–1118, doi:10.3762/bjoc.13.110

• processes in green solvents is a major challenge. Unfortunately, halogenated solvents such as dichloromethane (DCM), 1,2-dichloroethane (DCE) or aromatics such as benzene and toluene are the most frequently used solvents for metathesis reactions whereas these solvents possess serious health and

Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis

• Flavio Fanelli,
• Giovanna Parisi,
• Leonardo Degennaro and
• Renzo Luisi

Beilstein J. Org. Chem. 2017, 13, 520–542, doi:10.3762/bjoc.13.51

• reagents” chemistry with the continuous-flow photosynthesis of 6(5H)-phenanthridinones, poly(ADP-ribose) polymerase (PARP) inhibitors [69]. The relevance of the work resides in the use of green solvents, the absence of heavy metals, the use of convenient temperatures, and the increased safety by

N-Methylphthalimide-substituted benzimidazolium salts and PEPPSI Pd–NHC complexes: synthesis, characterization and catalytic activity in carbon–carbon bond-forming reactions

• Senem Akkoç,
• Yetkin Gök,
• İlhan Özer İlhan and
• Veysel Kayser

Beilstein J. Org. Chem. 2016, 12, 81–88, doi:10.3762/bjoc.12.9

• compounds in Suzuki–Miyaura cross-coupling reaction The Suzuki–Miyaura cross-coupling reaction, which has mostly been performed in organic solvents until recently, can now be performed using green solvents under mild conditions [29][30][31][32][33][34]. We used H2O with DMF as solvents in different

Olefin metathesis in air

• Lorenzo Piola,
• Fady Nahra and
• Steven P. Nolan

Beilstein J. Org. Chem. 2015, 11, 2038–2056, doi:10.3762/bjoc.11.221

• reaction with styrene, avoiding the use of hazardous diazo compound 7 [82]. Towards the end of 2013, a report by Olszewski, Skowerski and co-workers showed how a variety of commercially available catalysts (Figure 12) could be employed in air with nondegassed ACS grade green solvents. Their results were in

Nitro-Grela-type complexes containing iodides – robust and selective catalysts for olefin metathesis under challenging conditions

• Andrzej Tracz,
• Mateusz Matczak,
• Katarzyna Urbaniak and
• Krzysztof Skowerski

Beilstein J. Org. Chem. 2015, 11, 1823–1832, doi:10.3762/bjoc.11.198

• vicinity of ruthenium related to the presence of iodides ensures enhanced catalyst stability. The benefits are most apparent under challenging conditions, such as very low reaction concentrations, protic solvents or with the occurrence of impurities. Keywords: green solvents; macrocyclization; metathesis

• with fair yields (77% and 57% of 19 and 20, respectively) while other catalysts demonstrated less than a 10% yield. Metathesis in ACS-grade and “green” solvents Our continuous interest in the development of more sustainable, environmentally and user-friendly olefin metathesis has recently inspired us