Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent Cyrene^TM under one-pot conditions

• Zoltán Medgyesi and
• László T. Mika

Beilstein J. Org. Chem. 2025, 21, 1544–1551, doi:10.3762/bjoc.21.117

• important transformation exhibiting higher chemical and environmental safety. Keywords: alternative solvent; click chemistry; cycloaddition; CyreneTM; 1,2,3-triazoles; Introduction In the past few decades, transition-metal-catalyzed coupling and addition reactions have represented one of the most powerful

Reactivity of hypervalent iodine(III) reagents bearing a benzylamine with sulfenate salts

• Beatriz Dedeiras,
• Catarina S. Caldeira,
• José C. Cunha,
• Clara S. B. Gomes and
• M. Manuel B. Marques

Beilstein J. Org. Chem. 2024, 20, 3281–3289, doi:10.3762/bjoc.20.272

• reagent 2a in most organic solvents, an alternative solvent was tested; nevertheless, BBX 2a showed to be insoluble when using toluene (Table 1, entry 3). To have further insights on the formation of sulfonamide 5aa, an experiment was conducted under the same stoichiometric conditions that yielded product

(Bio)isosteres of ortho- and meta-substituted benzenes

• H. Erik Diepers and
• Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

• that the use of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as the solvent in the isomerisation reaction changes the obtained ratio in favour of the 1,3-cuneane when compared to their alternative solvent system of H2O/MeOH [72]. Iwabuchi and co-workers demonstrated the suitability of 1,3-cuneanes to

1-Butyl-3-methylimidazolium tetrafluoroborate as suitable solvent for BF₃: the case of alkyne hydration. Chemistry vs electrochemistry

• Marta David,
• Elisa Galli,
• Richard C. D. Brown,
• Marta Feroci,
• Fabrizio Vetica and
• Martina Bortolami

Beilstein J. Org. Chem. 2023, 19, 1966–1981, doi:10.3762/bjoc.19.147

• reused up to five times, without adversely affecting the reaction yields. Screening of different ionic liquids as media for the hydration of diphenylacetylene After the optimization of the reaction conditions in BMIm-BF4, different ILs were considered as alternative solvent (Table 2 and Table 3). All the

Total synthesis of insect sex pheromones: recent improvements based on iron-mediated cross-coupling chemistry

• Eric Gayon,
• Guillaume Lefèvre,
• Olivier Guerret,
• Adrien Tintar and
• Pablo Chourreu

Beilstein J. Org. Chem. 2023, 19, 158–166, doi:10.3762/bjoc.19.15

• quest for suitable additives as surrogates of NMP. Szostak and Bisz reported in 2019 that N-methyl-ε-caprolactame (NMCPL) could be used as an alternative solvent, and sp3–sp2 cross-coupling reactions proceeding with good to excellent yields were reported. Alkyl Grignard reagents could thus be used in

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

• in isolated yields were observed (Table 4, Table 5 and Table 6) verifying the wide range of functional group tolerance by side of acetylenic substrates, as well. Same results were reported by Alper and co-workers, who perform this reaction in [BMIM][PF6] as alternative solvent [22]. The possible

• alkoxyvalerate anion with HI that formed during the reaction could be assumed. Conclusion In conclusion, we have demonstrated that a γ-valerolactone-based ionic liquid, tetrabutylphosphonium 4-ethoxyvalerate can be utilized as an alternative solvent for Pd-catalyzed Sonogashira coupling reactions of aryl iodides

Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: toward the emergence of new building blocks

• Clémence Moitessier,
• Ahmad Rifai,
• Pierre-Edouard Danjou,
• Isabelle Mallard and
• Francine Cazier-Dennin

Beilstein J. Org. Chem. 2019, 15, 721–726, doi:10.3762/bjoc.15.67

• through a reaction of furfuryl alcohol with propargyl bromide, as is referred in the study of Cao et al. (Scheme 1) [17]. As a matter of fact, a modification of the purification step was done in order to quantitatively enhance the yield. An alternative solvent-free microwave-assisted organic synthesis

Fabrication of supramolecular cyclodextrin–fullerene nonwovens by electrospinning

• Hiroaki Yoshida,
• Ken Kikuta and
• Toshiyuki Kida

Beilstein J. Org. Chem. 2019, 15, 89–95, doi:10.3762/bjoc.15.10

• formation of the γ-CD–C60 complexes has been reported in both aqueous and organic media, including water [21], toluene/water [22], DMSO [23], and DMF/water [24], electrospinning is difficult due to the low solvent volatility. Therefore, an alternative solvent with a higher volatility must be explored to

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

• Adrián A. Heredia and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2017, 13, 910–918, doi:10.3762/bjoc.13.92

• with DMF and PEG 200, we chose PEG 200 as the solvent for subsequent reactions, which is a non-toxic and inexpensive biodegradable material also used as a sustainable and alternative solvent due to its reusability [39]. Table 2 summarizes the results for the screening and concentration of the base used

Development of a continuous process for α-thio-β-chloroacrylamide synthesis with enhanced control of a cascade transformation

• Olga C. Dennehy,
• Valérie M. Y. Cacheux,
• Benjamin J. Deadman,
• Denis Lynch,
• Stuart G. Collins,
• Humphrey A. Moynihan and
• Anita R. Maguire

Beilstein J. Org. Chem. 2016, 12, 2511–2522, doi:10.3762/bjoc.12.246

• as an alternative solvent. As 1H NMR analysis indicated that the crude reaction product from batch tests (using methanol as solvent) consisted of 98% α-thioamide 2, the process was subsequently transferred to a continuous flow system (Scheme 5). A variety of temperatures (60–120 °C), bases (NaOMe

• . Acetonitrile was considered as a possible alternative solvent due to the high solubility of NCS it offers. Hence, preliminary experiments were carried out in order to compare its performance to toluene (Table 3), with the α-thioamide 2:NCS ratio again adjusted by manipulating the concentration of the reagent

Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole

• Jacob R. Hauser,
• Hester A. Beard,
• Mary E. Bayana,
• Katherine E. Jolley,
• Stuart L. Warriner and
• Robin S. Bon

Beilstein J. Org. Chem. 2016, 12, 2019–2025, doi:10.3762/bjoc.12.189

• . In view of scale-up of the DABCO-catalysed cyanation of 6, an alternative solvent (mixture) was sought in order to eliminate safety issues and work-up problems resulting from the use of DMSO. An initial attempt to run the reaction in water failed because of the low aqueous solubility of 6 – resulting

Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

• Kirsty L. Wilson,
• Alan R. Kennedy,
• Jane Murray,
• Ben Greatrex,
• Craig Jamieson and
• Allan J. B. Watson

Beilstein J. Org. Chem. 2016, 12, 2005–2011, doi:10.3762/bjoc.12.187

• ][35], Mizoroki–Heck [36][37], Sonogashira [38], Stille [39], Hiyama reactions [40], and hydroformylation reactions [41]. In the current study, we present the use of Cyrene as an alternative solvent (direct DMF replacement) for the Sonogashira reaction, as well as related Cacchi-type annulations [42

Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium–zinc base and regioselectivity-computed CH acidity relationship

• Mohamed Yacine Ameur Messaoud,
• Ghenia Bentabed-Ababsa,
• Madani Hedidi,
• Aïcha Derdour,
• Floris Chevallier,
• Yury S. Halauko,
• Oleg A. Ivashkevich,
• Vadim E. Matulis,
• Laurent Picot,
• Valérie Thiéry,
• Thierry Roisnel,
• Vincent Dorcet and
• Florence Mongin

Beilstein J. Org. Chem. 2015, 11, 1475–1485, doi:10.3762/bjoc.11.160

• N-phenylpyrrole (1c). The result has been evidenced by subsequent iodolysis (Scheme 2). Nevertheless, for numerous substrates, THF is an alternative solvent that allows the reactions to be finished after 2 h contact at room temperature [33][34][36]. Among the different methods of trapping that can

Nonanebis(peroxoic acid): a stable peracid for oxidative bromination of aminoanthracene-9,10-dione

• Vilas Venunath Patil and
• Ganapati Subray Shankarling

Beilstein J. Org. Chem. 2014, 10, 921–928, doi:10.3762/bjoc.10.90

• important advantage is that it is stable at room temperature. Thus it can be a good alternative for the conventional peracids. In our previous work [11] (Scheme 1), we reported the use of biodegradable deep eutectic mixtures as an alternative solvent to conventional solvents. The reaction selectively gives

Kinetics and mechanism of vanadium catalysed asymmetric cyanohydrin synthesis in propylene carbonate

• Michael North and
• Marta Omedes-Pujol

Beilstein J. Org. Chem. 2010, 6, 1043–1055, doi:10.3762/bjoc.6.119

• carbonate, thus providing a green, alternative solvent to dichloromethane. Reactions in propylene carbonate are slower and less enantioselective than those carried out in dichloromethane; though by optimization of the reaction conditions, high enantioselectivities can still be obtained. A study of the

Study of thioglycosylation in ionic liquids

• Jianguo Zhang and
• Arthur Ragauskas

Beilstein J. Org. Chem. 2006, 2, No. 12, doi:10.1186/1860-5397-2-12

• volatile organic solvents that have broader environmental concerns.[3] These drawbacks have been well documented and have driven, in part, the quest for alternative solvent systems. Ionic liquids possess several attractive properties such as, no measurable vapor pressure, nonflammable, water and air