Green chemistry III: Technologies shaping future directions in synthesis
Prof. Anna G. Slater, University of Liverpool
Prof. Luigi Vaccaro, Università di Perugia
Prof. Yanlong Gu, Huazhong University of Science and Technology
This thematic issue highlights advancements toward a greener and more sustainable field of organic chemistry. We welcome contributions from all areas of organic chemistry to comprehensively showcase its vital strategic role in building a sustainable future.
Chemical synthesis is already central to life and society and has a fundamental role to play in delivering a sustainable future. The discovery, optimization, and scalable manufacture of molecules and materials is pivotal for challenges such as the transition to green energy, resilient food production, and emerging healthcare needs. To meet these needs, both creative synthetic strategies and enabling tools and technologies are required.
We aim to cover topics such as photo-, electro-, mechano-, microwave, continuous-flow, automated, and plasma chemistry, alongside the diverse chemical fields that benefit from them, including organic synthesis, catalysis, biocatalysis, materials chemistry, and medicinal chemistry. By focusing on innovative eco-friendly methodologies and the development of sustainable processes and materials, we aim to highlight how organic chemistry can contribute to solving environmental challenges and promoting a healthier planet.
Our thematic issue builds upon the success of the previous thematic issues devoted to green chemistry (please see here for edition I and edition II).
Submission deadline: April 30, 2026
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Recent advances in the electrochemical synthesis of organophosphorus compounds
- Babak Kaboudin,
- Milad Behroozi,
- Sepideh Sadighi and
- Fatemeh Asgharzadeh
Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61
Graphical Abstract
Scheme 1: Electrosynthesis of phenanthridine phosphine oxides.
Scheme 2: Electrosynthesis of 1-aminoalkylphosphine oxides.
Scheme 3: Various electrochemical C–P coupling reactions.
Scheme 4: Electrochemical C–P coupling reaction of indolines.
Scheme 5: Electrochemical C–P coupling reaction of ferrocene.
Scheme 6: Electrochemical C–P coupling reaction of acridines with phosphites.
Scheme 7: Electrochemical C–P coupling reaction of alkenes.
Scheme 8: Electrochemical C–P coupling reaction of arenes in a flow system.
Scheme 9: Electrochemical C–P coupling reaction of heteroarenes.
Scheme 10: Electrochemical C–P coupling reaction of thiazoles.
Scheme 11: Electrochemical C–P coupling reaction of indole derivatives.
Scheme 12: Electrosynthesis of 1-amino phosphonates.
Scheme 13: Electrochemical C–P coupling reaction of aryl and vinyl bromides.
Scheme 14: Electrochemical C–P coupling reaction of phenylpyridine with dialkyl phosphonates in the presence o...
Scheme 15: Electrochemical P–C bond formation of amides.
Scheme 16: Electrochemical synthesis of α-hydroxy phosphine oxides.
Scheme 17: Electrochemical synthesis of π-conjugated phosphonium salts.
Scheme 18: Electrochemical phosphorylation of indoles.
Scheme 19: Electrochemical synthesis of phosphorylated propargyl alcohols.
Scheme 20: Electrochemical synthesis of phosphoramidates.
Scheme 21: Electrochemical reaction of carbazole with diphenylphosphine.
Scheme 22: Electrochemical P–N coupling of carbazole with phosphine oxides.
Scheme 23: Electrochemical P–N coupling of indoles with a trialkyl phosphite.
Scheme 24: Electrochemical synthesis of iminophosphoranes.
Scheme 25: Electrochemical P–O coupling of phenols with dialkyl phosphonate.
Scheme 26: Electrochemical P–O coupling of alcohols with diphenylphosphine.
Scheme 27: Electrochemical P–S coupling of thiols with dialkylphosphines.
Scheme 28: Electrochemical thiophosphorylation of indolizines.
Scheme 29: Electrosynthesis of S-heteroaryl phosphorothioates.
Scheme 30: Electrochemical phosphorylation reactions.
Scheme 31: Electrochemical P–Se formation.
Scheme 32: Electrochemical selenation/halogenation of alkynyl phosphonates.
Scheme 33: Electrochemical enantioselective aryl C–H bond activation.
Chitosan-supported CuI-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazolinones
- Xuhong Zhao,
- Weishuang Li,
- Mengli Yang,
- Bojie Li,
- Yaoyao Zhang,
- Lizhen Huang and
- Lei Zhu
Beilstein J. Org. Chem. 2025, 21, 839–844, doi:10.3762/bjoc.21.67
Graphical Abstract
Scheme 1: Copper-catalyzed cascade reaction of 2-halobenzoic acids and amidines for the synthesis of quinazol...
Scheme 2: Substrate scope. Reaction conditions: 1 (0.5 mmol, 1.0 equiv), amidines hydrochloride 2 (0.75 mmol,...
Scheme 3: Proposed mechanism for the CS@CuI-catalyzed synthesis of quinazolinones.
Scheme 4: Scaling-up experiment (a) and recyclability of CS@CuI (b).
A multicomponent reaction-initiated synthesis of imidazopyridine-fused isoquinolinones
- Ashutosh Nath,
- John Mark Awad and
- Wei Zhang
Beilstein J. Org. Chem. 2025, 21, 1161–1169, doi:10.3762/bjoc.21.92
Graphical Abstract
Figure 1: Bioactive compounds bearing imidazopyridine (red) and isoquinolinone-kind (blue) rings.
Scheme 1: GBB-initiated synthesis of imidazopyridine-fused isoquinolinones.
Scheme 2: GBB reaction and N-acylation for the preparation of imidazo[1,2-a]pyridines 6.
Scheme 3: Substrate scope for IMDA and dehydrative aromatization in making 8. Reaction conditions: 6 and AlCl3...
Figure 2: Transition state analysis of IMDA reactions for 6a, 6j, 6h and 6r.
Figure 3: Relative energy diagram for the synthesis of 8a from 6a.
Scheme 4: Using thiophene-2-carbaldehyde for the synthesis of 8t.
Scheme 5: Proposed mechanisms for IMDA reaction and dehydration re-aromatization.
Recent advances in amidyl radical-mediated photocatalytic direct intermolecular hydrogen atom transfer
- Hao-Sen Wang,
- Lin Li,
- Xin Chen,
- Jian-Li Wu,
- Kai Sun,
- Xiao-Lan Chen,
- Ling-Bo Qu and
- Bing Yu
Beilstein J. Org. Chem. 2025, 21, 1306–1323, doi:10.3762/bjoc.21.100
Graphical Abstract
Figure 1: (a) BDE of C–H. (b) Direct functionalization of C–H catalyzed by transition-metal. (c) Direct funct...
Figure 2: (a) Amidyl radical-enabled hydrogen atom transfer. (b) Substituent effects to amidyl radical proper...
Figure 3: Representative photocatalysts discussed in this review.
Scheme 1: Alkylation of C(sp3)–H catalyzed by amidyl radical under visible light.
Scheme 2: Direct heteroarylation of C(sp3)–H catalyzed by amidyl radical under visible light.
Scheme 3: Alkylation of C(sp3)–H catalyzed by amidyl radical and metal-free photocatalyst under visible light....
Scheme 4: Alkylation of C(sp3)–H, Si–H, and Ge–H catalyzed by amidyl radical under visible light.
Scheme 5: Direct heteroarylation of C(sp3)–H catalyzed by synergistic promotion of amidyl radical and photoca...
Scheme 6: Direct B–H functionalization of icosahedral carboranes catalyzed by amidyl radical under visible li...
Scheme 7: Nucleophilic amination of C(sp3)–H enabled by amidyl radical under visible light.
Scheme 8: Direct heteroarylation of C(sp3)–H and C(sp3)–H without the presence of strong bases, acids, or oxi...
Scheme 9: Xanthylation of C(sp3)–H addressed by amidyl radical under visible light.
Scheme 10: Xanthylation of C(sp3)–H in polyolefins addressed by amidyl radical under visible light.
Scheme 11: Site-selective C(sp3)–H bromination implemented by amidyl radical under visible light.
Scheme 12: Site-selective chlorination of C(sp3)–H in natural products implemented by amidyl radical under vis...
Scheme 13: Alkylation of C(sp3)–H catalyzed by amidyl radical photocatalyst under visible light.
High-pressure activation for the solvent- and catalyst-free syntheses of heterocycles, pharmaceuticals and esters
- Kelsey Plasse,
- Valerie Wright,
- Guoshu Xie,
- R. Bernadett Vlocskó,
- Alexander Lazarev and
- Béla Török
Beilstein J. Org. Chem. 2025, 21, 1374–1387, doi:10.3762/bjoc.21.102
Graphical Abstract
Figure 1: Simplified schematic rendering of a high hydrostatic pressure reactor.
Scheme 1: High pressure-initiated synthesis of 1,3-dihydrobenzimidazoles 3a–d. The yields are GC yields and t...
Figure 2: Illustration of the cyclization reaction between chalcone (4) and 3-(trifluoromethyl)phenylhydrazin...
Scheme 2: High pressure-initiated catalyst- and solvent-free synthesis of pyrazoles 6a–c from chalcone (4) an...
Figure 3: Schematic representation of the cycling experiments: the major variables are the applied pressure, ...
Scheme 3: High pressure-initiated synthesis of the active pharmaceutical ingredients in Tylenol® and Aspirin®...
Scheme 4: High pressure-initiated esterification of alcohols 12a–g in a catalyst- and additional solvent-free...
Scheme 5: High pressure-initiated large scale syntheses of N-aryl- and N-alkylpyrroles at about 100 g scale.
Azide–alkyne cycloaddition (click) reaction in biomass-derived solvent CyreneTM under one-pot conditions
- Zoltán Medgyesi and
- László T. Mika
Beilstein J. Org. Chem. 2025, 21, 1544–1551, doi:10.3762/bjoc.21.117
Graphical Abstract
Scheme 1: Synthesis of CyreneTM (dihydrolevoglucosenone) from cellulose-based feeds via levoglucosenone (LG).
Scheme 2: Copper-catalyzed azide–alkyne cycloaddition of benzyl azide (1a) and phenylacetylene (2a) in variou...
Figure 1: Comparison of various solvents used in the CuAAC reaction. Reaction conditions: 1.15 mmol benzyl az...
Figure 2: Effect of the Cu source used in the click reaction of benzyl azide (1a, 1.15 mmol) and phenylacetyl...
Figure 3: Copper-catalyzed azide–alkyne cycloaddition of benzyl azide (1a) and various acetylenes 2a–h in Cyr...
Figure 4: Consecutive synthesis of various N-substituted-4-phenyl-1H-1,2,3-triazoles in CyreneTM. Reaction co...
Figure 5: “One-pot” synthesis of various 1-allyl-4-substituted-1H-1,2,3-triazoles in CyreneTM. Reaction condi...
Figure 6: Solvent recovery for the CuAAC reaction of 1a and 2a. Reaction conditions: 12.5 mL CyreneTM, 1 mol ...
Fe-catalyzed efficient synthesis of 2,4- and 4-substituted quinolines via C(sp2)–C(sp2) bond scission of styrenes
- Prafull A. Jagtap,
- Manish M. Petkar,
- Vaishnavi R. Sawant and
- Bhalchandra M. Bhanage
Beilstein J. Org. Chem. 2025, 21, 1799–1807, doi:10.3762/bjoc.21.142
Graphical Abstract
Figure 1: Representative examples of bioactive quinolines.
Scheme 1: C(sp2)–C(sp2) bond-cleavage strategies for quinoline synthesis.
Scheme 2: Substrate scope of various arylamines and styrenes.
Scheme 3: Scale-up studies for the synthesis of antifungal agents.
Scheme 4: Mechanistic investigations.
Scheme 5: Plausible reaction mechanism.
Stereoselective electrochemical intramolecular imino-pinacol reaction: a straightforward entry to enantiopure piperazines
- Margherita Gazzotti,
- Fabrizio Medici,
- Valerio Chiroli,
- Laura Raimondi,
- Sergio Rossi and
- Maurizio Benaglia
Beilstein J. Org. Chem. 2025, 21, 1897–1908, doi:10.3762/bjoc.21.147
Graphical Abstract
Scheme 1: Synthesis of vicinal diamines via imino-pinacol coupling in the presence of metal-based reductants.
Scheme 2: Light-promoted imino-pinacol coupling for the synthesis of vicinal diamines.
Scheme 3: Historical perspective on electrochemical imino-coupling protocols.
Scheme 4: Stereoselective electroreductive intramolecular imino-pinacol reaction.
Scheme 5: Scope of the imino-pinacol coupling reaction. Reaction conditions: GC electrodes, NEt4BF4 (2.6 equi...
Figure 1: X-ray determined structure of chiral piperazine 2b.
Scheme 6: Continuous flow synthesis of piperazine 2a. The yield was determined by 1H NMR spectroscopy using 1...
Scheme 7: Proposed reaction mechanism.
Scheme 8: Cyclic voltammetry investigation. Cyclic voltammetry of a 0.325 M solution of Et4NBF4 in DMF (light...
C2 to C6 biobased carbonyl platforms for fine chemistry
- Jingjing Jiang,
- Muhammad Noman Haider Tariq,
- Florence Popowycz,
- Yanlong Gu and
- Yves Queneau
Beilstein J. Org. Chem. 2025, 21, 2103–2172, doi:10.3762/bjoc.21.165
Graphical Abstract
Figure 1: C2–C6 biobased carbonyl building blocks.
Scheme 1: Proposed (2 + 2) route to glycolaldehyde and glycolic acid from erythritol by Cu/AC catalyst (AC = ...
Scheme 2: Reductive amination of GCA.
Scheme 3: N-Formylation of secondary amines by reaction with GCA.
Scheme 4: Synthesis and conversion of hydroxy acetals to cyclic acetals.
Scheme 5: Synthesis of 3-(indol-3-yl)-2,3-dihydrofurans via three-component reaction of glycolaldehyde, indol...
Scheme 6: BiCl3-catalyzed synthesis of benzo[a]carbazoles from 2-arylindoles and α-bromoacetaldehyde ethylene...
Scheme 7: Cu/NCNSs-based conversion of glycerol to glycolic acid and other short biobased acids.
Scheme 8: E. coli-based biotransformation of C1 source molecules (CH4, CO2 and CO) towards C2 glycolic acid.
Scheme 9: N-Formylation of amines with C2 (a) or C3 (b) biomass-based feedstocks.
Scheme 10: Methods for the formation of propanoic acid (PA) from lactic acid (LA).
Scheme 11: Co-polymerization of biobased lactic acid and glycolic acid via a bicatalytic process.
Scheme 12: Oxidation of α-hydroxy acids by tetrachloroaurate(III) in acetic acid–sodium acetate buffer medium.
Figure 2: Selective catalytic pathways for the conversion of lactic acid (LA).
Scheme 13: Synthesis of 1,3-PDO via cross-aldol reaction between formaldehyde and acetaldehyde to 3-hydroxypro...
Scheme 14: Hydrothermal conversion of 1,3-dihydroxy-2-propane and 2,3-dihydroxypropanal to methylglyoxal.
Scheme 15: FLS-catalyzed formose reaction to synthesize GA and DHA.
Scheme 16: GCA and DHA oxidation products of glycerol and isomerization of GCA to DHA under flow conditions us...
Scheme 17: Acid-catalyzed reactions of DHA with alcohols.
Scheme 18: Synthesis of dihydroxyacetone phosphate from dihydroxyacetone.
Scheme 19: Bifunctional acid–base catalyst DHA conversion into lactic acid via pyruvaldehyde or fructose forma...
Scheme 20: Catalytic one-pot synthesis of GA and co-synthesis of formamides and formates from DHA.
Scheme 21: (a) Synthesis of furan derivatives and (b) synthesis of thiophene derivative by cascade [3 + 2] ann...
Scheme 22: Brønsted acidic ionic liquid catalyzed synthesis of benzo[a]carbazole from renewable acetol and 2-p...
Scheme 23: Asymmetric hydrogenation of α-hydroxy ketones to 1,2-diols.
Scheme 24: Synthesis of novel 6-(substituted benzylidene)-2-methylthiazolo [2,3-b]oxazol-5(6H)-one from 1-hydr...
Scheme 25: ʟ-Proline-catalyzed synthesis of anti-diols from hydroxyacetone and aldehydes.
Scheme 26: C–C-bond-formation reactions of a biomass-based feedstock aromatic aldehyde (C5) and hydroxyacetone...
Scheme 27: Ethanol upgrading to C4 bulk chemicals via the thiamine (VB1)-catalyzed acetoin condensation.
Scheme 28: One-pot sequential chemoenzymatic synthesis of 2-aminobutane-1,4-diol and 1,2,4-butanetriol via 1,4...
Scheme 29: Synthesis of 1,4-dihydroxybutan-2-one by microbial transformation.
Scheme 30: Conversion of polyols by [neocuproine)Pd(OAc)]2(OTf)2] to α-hydroxy ketones.
Scheme 31: Chemoselective oxidation of alcohols with chiral palladium-based catalyst 2.
Scheme 32: Electrochemical transformation of furfural to 5-hydroxy-2(5H)-furanone (HFO).
Scheme 33: Selective hydrodeoxygenation of HFO and oxidation to γ-butyrolactone (GBL).
Scheme 34: Photosensitized oxygenation of furan towards HFO via ozonide intermediates.
Scheme 35: Conversion of furfural to HFO and MAN by using mesoporous carbon nitride (SGCN) as photocatalyst.
Scheme 36: Synthesis of HFO from furan derivatives.
Scheme 37: Photooxidation of furfural to 5-hydroxy-2(5H)-furanone (HFO).
Scheme 38: Synthesis of Friedel–Crafts indole adduct from HFO.
Scheme 39: Conversion of HFO to α,γ-substituted chiral γ-lactones.
Scheme 40: Tautomeric transformation of HFO to formylacrylic acid.
Scheme 41: Hydrolysis of HFO to succinic acid in aqueous solution.
Scheme 42: Substitution and condensation reactions of 5-hydroxy-2(5H)-furanone (HFO).
Scheme 43: (a) Conversion of HFO towards valuable C4 chemicals and (b) anodic oxidation of 5-hydroxy-2(5H)-fur...
Figure 3: Conversion of HFO towards other natural and synthetic substances.
Scheme 44: Conversion of furfural to maleic anhydride (reaction a: VOx/Al2O3; reaction b: VPO).
Scheme 45: Conversion of furfural into succinic acid.
Scheme 46: Electro‑, photo‑, and biocatalysis for one-pot selective conversions of furfural into C4 chemicals.
Scheme 47: Production route of furfural from hemicellulose.
Scheme 48: Mechanism for xylose dehydration to furfural through a choline xyloside intermediate.
Scheme 49: Conversion of furfural to furfuryl alcohol and its derivatives.
Scheme 50: Conversion of furfural to furfuryl alcohol and 3-(2-furyl)acrolein.
Scheme 51: The aerobic oxidative condensation of biomass-derived furfural and linear alcohols.
Scheme 52: The single-step synthesis of 2-pentanone from furfural.
Scheme 53: Electrocatalytic coupling reaction of furfural and levulinic acid.
Scheme 54: Conversion of furfural to m-xylylenediamine.
Scheme 55: Conversion of furfural to tetrahydrofuran-derived amines.
Scheme 56: Formation of trans-4,5-diamino-cyclopent-2-enones from furfural.
Scheme 57: Production of pyrrole and proline from furfural.
Scheme 58: Synthesis of 1‑(trifluoromethyl)-8-oxabicyclo[3.2.1]oct-3-en-2-ones from furfural.
Scheme 59: Conversion of furfural to furfural-derived diacids.
Scheme 60: A telescope protocol derived from furfural and glycerol.
Scheme 61: A tandem cyclization of furfural and 5,5-dimethyl-1,3-cyclohexanedione.
Scheme 62: A Ugi four-component reaction to construct furfural-based polyamides.
Scheme 63: One-pot synthesis of γ-acyloxy-Cy7 from furfural.
Scheme 64: Dimerization–Piancatelli sequence toward humins precursors from furfural.
Scheme 65: Conversion of furfural to CPN.
Scheme 66: Synthesis of jet fuels range cycloalkanes from CPN and lignin-derived vanillin.
Scheme 67: Solar-energy-driven synthesis of high-density biofuels from CPN.
Scheme 68: Reductive amination of CPN to cyclopentylamine.
Scheme 69: Asymmetric hydrogenation of C=O bonds of exocyclic α,β-unsaturated cyclopentanones.
Scheme 70: Preparation of levulinic acid via the C5 route (route a) or C6 route (routes b1 and b2).
Scheme 71: Mechanism of the rehydration of HMF to levulinic acid and formic acid.
Scheme 72: Important levulinic acid-derived chemicals.
Scheme 73: Direct conversion of levulinic acid to pentanoic acid.
Scheme 74: Catalytic aerobic oxidation of levulinic acid to citramalic acid.
Scheme 75: Conversion of levulinic acid to 1,4-pentanediol (a) see ref. [236]; b) see ref. [237]; c) see ref. [238]; d) see r...
Scheme 76: Selective production of 2-butanol through hydrogenolysis of levulinic acid.
Scheme 77: General reaction pathways proposed for the formation of 5MPs from levulinic acid.
Scheme 78: Selective reductive amination of levulinic acid to N-substituted pyrroles.
Scheme 79: Reductive amination of levulinic acid to chiral pyrrolidinone.
Scheme 80: Reductive amination of levulinic acid to non-natural chiral γ-amino acid.
Scheme 81: Nitrogen-containing chemicals derived from levulinic acid.
Scheme 82: Preparation of GVL from levulinic acid by dehydration and hydrogenation.
Scheme 83: Ruthenium-catalyzed levulinic acid to chiral γ-valerolactone.
Scheme 84: Catalytic asymmetric hydrogenation of levulinic acid to chiral GVL.
Scheme 85: Three steps synthesis of ε-caprolactam from GVL.
Scheme 86: Multistep synthesis of nylon 6,6 from GVL.
Scheme 87: Preparation of MeGVL by α-alkylation of GVL.
Scheme 88: Ring-opening polymerization of five-membered lactones.
Scheme 89: Synthesis of GVL-based ionic liquids.
Scheme 90: Preparation of butene isomers from GVL under Lewis acid conditions.
Scheme 91: Construction of C5–C12 fuels from GVL over nano-HZSM-5 catalysts.
Scheme 92: Preparation of alkyl valerate from GVL via ring opening/reduction/esterification sequence.
Scheme 93: Construction of 4-acyloxypentanoic acids from GVL.
Scheme 94: Synthesis of 1,4-pentanediol (PDO) from GVL.
Scheme 95: Construction of novel cyclic hemiketal platforms via self-Claisen condensation of GVL.
Scheme 96: Copper-catalyzed lactamization of GVL.
Figure 4: Main scaffolds obtained from HMF.
Scheme 97: Biginelli reactions towards HMF-containing dihydropyrimidinones.
Scheme 98: Hantzsch dihydropyridine synthesis involving HMF.
Scheme 99: The Kabachnik–Fields reaction involving HMF.
Scheme 100: Construction of oxazolidinone from HMF.
Scheme 101: Construction of rhodamine-furan hybrids from HMF.
Scheme 102: A Groebke–Blackburn–Bienaymé reaction involving HMF.
Scheme 103: HMF-containing benzodiazepines by [4 + 2 + 1] cycloadditions.
Scheme 104: Synthesis of fluorinated analogues of α-aryl ketones.
Scheme 105: Synthesis of HMF derived disubstituted γ-butyrolactone.
Scheme 106: Functionalized aromatics from furfural and HMF.
Scheme 107: Diels–Alder adducts from HMF or furfural with N-methylmaleimide.
Scheme 108: Pathway of the one-pot conversion of HMF into phthalic anhydride.
Scheme 109: Photocatalyzed preparation of humins (L-H) from HMF mixed with spoiled HMF residues (LMW-H) and fur...
Scheme 110: Asymmetric dipolar cycloadditions on HMF.
Scheme 111: Dipolar cycloadditions of HMF based nitrones to 3,4- and 3,5-substituted isoxazolidines.
Scheme 112: Production of δ-lactone-fused cyclopenten-2-ones from HMF.
Scheme 113: Aza-Piancatelli access to aza-spirocycles from HMF-derived intermediates.
Scheme 114: Cross-condensation of furfural, acetone and HMF into C13, C14 and C15 products.
Scheme 115: Base-catalyzed aldol condensation/dehydration sequences from HMF.
Scheme 116: Condensation of HMF and active methylene nitrile.
Scheme 117: MBH reactions involving HMF.
Scheme 118: Synthesis of HMF-derived ionic liquids.
Scheme 119: Reductive amination/enzymatic acylation sequence towards HMF-based surfactants.
Scheme 120: The formation of 5-chloromethylfurfural (CMF).
Scheme 121: Conversion of CMF to HMF, levulinic acid, and alkyl levulinates.
Scheme 122: Conversion of CMF to CMFCC and FDCC.
Scheme 123: Conversion of CMF to BHMF.
Scheme 124: Conversion of CMF to DMF.
Scheme 125: CMF chlorine atom substitutions toward HMF ethers and esters.
Scheme 126: Introduction of carbon nucleophiles in CMF.
Scheme 127: NHC-catalyzed remote enantioselective Mannich-type reactions of CMF.
Scheme 128: Conversion of CMF to promising biomass-derived dyes.
Scheme 129: Radical transformation of CMF with styrenes.
Scheme 130: Synthesis of natural herbicide δ-aminolevulinic acid from CMF.
Scheme 131: Four step synthesis of the drug ranitidine from CMF.
Scheme 132: Pd/CO2 cooperative catalysis for the production of HHD and HXD.
Scheme 133: Different ruthenium (Ru) catalysts for the ring-opening of 5-HMF to HHD.
Scheme 134: Proposed pathways for preparing HXD from HMF.
Scheme 135: MCP formation and uses.
Scheme 136: Cu(I)-catalyzed highly selective oxidation of HHD to 2,5-dioxohexanal.
Scheme 137: Synthesis of N‑substituted 3‑hydroxypyridinium salts from 2,5-dioxohexanal.
Scheme 138: Ru catalyzed hydrogenations of HHD to 1,2,5-hexanetriol (a) see ref. [396]; b) see ref. [397]).
Scheme 139: Aviation fuel range quadricyclanes produced by HXD.
Scheme 140: Synthesis of HDGK from HXD and glycerol as a chain extender.
Scheme 141: Synthesis of serinol pyrrole from HXD and serinol.
Scheme 142: Synthesis of pyrroles from HXD and nitroarenes.
Scheme 143: Two-step production of PX from cellulose via HXD.
Scheme 144: Preparation of HCPN from HMF via hydrogenation and ring rearrangement.
Scheme 145: Suggested pathways from HMF to HCPN.
Scheme 146: α-Alkylation of HCPN with ethylene gas.
Scheme 147: Synthesis of 3-(hydroxymethyl)cyclopentylamine from HMF via reductive amination of HCPN.
Scheme 148: Production of LGO and Cyrene® from biomass.
Scheme 149: Synthesis of HBO from LGO and other applications.
Scheme 150: Construction of m-Cyrene® homopolymer.
Scheme 151: Conversion of Cyrene® to THFDM and 1,6-hexanediol.
Scheme 152: RAFT co-polymerization of LGO and butadienes.
Scheme 153: Polycondensation of HO-LGOL and diols with dimethyl adipate.
Scheme 154: Self-condensation of Cyrene® and Claisen–Schmidt reactions.
Scheme 155: Synthesis of 5-amino-2-(hydroxymethyl)tetrahydropyran from Cyrene®.
The high potential of methyl laurate as a recyclable competitor to conventional toxic solvents in [3 + 2] cycloaddition reactions
- Ayhan Yıldırım and
- Mustafa Göker
Beilstein J. Org. Chem. 2025, 21, 2389–2415, doi:10.3762/bjoc.21.184
Graphical Abstract
Figure 1: Versatile compounds via cycloaddition reactions.
Scheme 1: Molecular structures of parent compounds 1a–f, 2a–d and cycloadducts 3a–u.
Figure 2: a) Radar view of the physical properties of methyl laurate. b) Oral toxicity values of methyl laura...
Figure 3: The oral toxicity values of all the solvents utilized in the present study obtained with ProTox 3.0....
Figure 4: Ecological, environmental risk assessments, pesticide similarity and biodegradability assessments o...
Figure 5: Ecological, environmental risk assessments, pesticide similarity and biodegradability assessments o...
Figure 6: Ecological, environmental risk assessments, pesticide similarity and biodegradability assessments o...
Figure 7: Various toxicity parameters of methyl laurate and a series of other solvents calculated by ADMETLab...
Figure 8: a) Visualization of the localization of conventional organic and bio-based solvents in the Hansen s...
Figure 9: Vapour pressures of the solvents used (values retrieved from the Chemeo molecular database).
Scheme 2: Endo and exo stereoisomeric approaches of nitrone 1a and maleimide 2a in [3 + 2] cycloaddition reac...
Figure 10: Signals of protons used in the calculation of the diastereomeric ratios (cis/trans) of cycloadditio...
Figure 11: Results of studies on the recovery of solvents used in the reaction.
Figure 12: Simplified scheme describing the reaction monitoring and solvent recovery.
Figure 13: a) The superimposed spectra of C,N-diphenylnitrone and N-phenylmaleimide. b) The spectrum of methyl...
