Abstract
Fluorine-containing heterocycles play a crucial role in the pharmaceutical, agrochemical, and materials industries. The pursuit of effective and sustainable synthesis methods has driven the development of mechanochemistry as a solvent-free, energy-efficient alternative to conventional chemical transformations. Among these approaches, ball milling has emerged as a particularly promising technique for facilitating chemical reactions. This review covers key achievements over the past decade in the mechanochemical synthesis of fluorinated heterocyclic compounds for bimolecular, trimolecular, and tetramolecular reactions as well as transformations classified as peripheral functionalization of the heterocyclic framework. This work serves as a valuable resource for researchers and practitioners seeking to develop sustainable and efficient catalytic systems for fluorinated heterocyclic synthesis.
References
Friščić T., Mottillo C., Titi H.M. Mechanochemistry for Synthesis. Angew. Chem., Int. Ed. 2020. 59(3): 1018–1029.
doi.org/10.1002/ange.201906755.
Fernandez-Bertran J.F. Mechanochemistry: an overview. Pure Appl. Chem. 1999. 71(4): 581–586.
doi.org/10.1351/pac199971040581.
Howard J.L., Cao Q., Browne D.L. Mechanochemistry as an emerging tool for molecular synthesis: what can it offer? Chem. Sci. 2018. 9(12): 3080–3094.
doi: 10.1039/C7SC05371A.
Guo X., Xiang D., Duan G., Mou P. A review of mechanochemistry applications in waste management. Waste Manag. 2010. 30(1): 4–10.
doi.org/10.1016/j.wasman.2009.08.017.
Liu X., Li Y., Zeng L. et al. A review on mechanochemistry: approaching advanced energy materials with greener force. Advan. Mat. 2022. 34(46): 2108327.
doi.org/10.1002/adma.202108327.
Fantozzi N., Volle J.N., Porcheddu A. et al. Green metrics in mechanochemistry. Chem. Soc. Rev. 2023. 52(19): 6680–6714.
doi: 10.1039/D2CS00997H.
Nasser A., Mingelgrin U. Mechanochemistry: A review of surface reactions and environmental applications. App. Clay Sci. 2012. 67: 141–150.
doi.org/10.1016/j.clay.2011.11.018.
Ali W.A., Richards S.E., Alzard R.H. Unlocking the potential of ball milling for nanomaterial Synthesis: An overview. J Ind. Engin. Chem. 2025. doi.org/10.1016/j.jiec.2025.01.054.
Takacs L. Self-sustaining reactions induced by ball milling. Prog. Mat. Sci. 2002. 47(4): 355–414.
doi.org/10.1016/S0079-6425(01)00002-0.
Tao C.A., Wang J.F. Synthesis of metal organic frameworks by ball-milling. Crystals. 2020. 11(1): 15.
doi.org/10.3390/cryst11010015.
Roy K., Sahoo S., Saha A., Adak L. Ball milling in organic transformations. Curr. Org. Chem. 2023. 27(3): 153–165.
doi.org/10.2174/1385272827666221223143844.
Achar T.K., Bose A., Mal P. Mechanochemical synthesis of small organic molecules. Beilstein J. Org. Chem. 2017. 13(1): 1907–1931.
doi.org/10.3762/bjoc.13.186.
Juribasic M., Halasz I., Babic D. et al. Aging and Ball-Milling as Low-Energy and Environmentally Friendly Methods for the Synthesis of Pd(II) Photosensitizers. Organometallics. 2014. 33(5): 1227–1234.
doi.org/10.1021/om500008v.
Leitch J.A., Smallman H.R., Browne D.L. Solvent-minimized synthesis of 4CzIPN and related organic fluorophores via ball milling. J. Org. Chem. 2021. 86(20): 14095–14101.
doi.org/10.1021/acs.joc.1c01233.
Sahoo P.K., Bose A., Mal P. Solvent‐Free Ball‐Milling Biginelli Reaction by Subcomponent Synthesis. Eur. J. Org. Chem. 2015. (32): 6994–6998. doi.org/10.1002/ejoc.201501039.
Maurin O., Verdié P., Subra G. et al. Peptide synthesis: ball-milling, in solution, or on solid support, what is the best strategy? Beilstein J. Org. Chem. 2017. 13(1): 2087–2093.
doi.org/10.3762/bjoc.13.206.
Obst M., König B. Organic synthesis without conventional solvents. Eur. J. Org. Chem. 2018. (31): 4213–4232.
doi.org/10.1002/ejoc.201800556.
Margetić D. A synopsis of ball milling organic synthesis in the last 25 years. Curr. Org. Chem. 2023. 27(7): 580–584.
doi.org/10.2174/1385272827666230407082210.
Su W., Yu J., Li Z., Jiang Z. Solvent-free cross-dehydrogenative coupling reactions under high speed ball-milling conditions applied to the synthesis of functionalized tetrahydroisoquinolines. J. Org. Chem. 2011. 76(21): 9144–9150.
doi.org/10.1021/jo2015533.
Claramunt R.M., Lopez C., Sanz D., Elguero J. Mechano heterocyclic chemistry: Grinding and ball mills. Adv. Heterocycl. Chem. 2014. 112: 117–143.
doi.org/10.1016/B978-0-12-800171-4.00003-2.
Han J., Konno H., Sato T., Soloshonok V.A., Izawa K. Tailor-made amino acids in the design of small-molecule blockbuster drugs. Eur. J. Med. Chem. 2021. 220: 113448.
doi: 10.1016/j.ejmech.2021.113448.
Mei H., Han J., White S. et al. Tailor-made amino acids and fluorinated motifs as prominent traits in modern pharmaceuticals. Chem.—Eur. J. 2020. 26(50): 11349–11390.
doi: 10.1002/chem.202000617.
Han J., Konno H., Sato T. et al. Peptidomimetics and Peptide-Based Blockbuster Drugs. Curr. Org. Chem. 2021. 25(14): 1627–1658.
doi: 10.2174/1385272825666210610155047.
Han J., Remete A.M., Dobson L.S. et al. Next generation organofluorine containing blockbuster drugs. J. Fluor. Chem. 2020. 239: 109639.
doi.org/10.1016/j.jfluchem.2020.109639.
Liu J., Han J., Izawa K. et al. Cyclic tailor-made amino acids in the design of modern pharmaceuticals. Eur. J. Med. Chem. 2020. 208: 112736.
doi: 10.1016/j.ejmech.2020.112736.
Mei H., Han J., Fustero S. et al. Fluorine‐Containing Drugs Approved by the FDA in 2018. Chem.—Eur. J. 2019. 25(51): 11797–11819.
doi: 10.1002/chem.201901840.
Wang Q., Bian Y., Dhawan G. et al. FDA approved fluorine-containing drugs in 2023. Chin. Chem. Lett. 2024. 35(11): 109780.
doi: 10.1016/j.cclet.2024.109780.
Mei H., Remete A.M., Zou Y. et al. Fluorine-containing drugs approved by the FDA in 2019. Chin. Chem. Lett. 2020. 31(9): 2401–2413.
doi: 10.1016/j.cclet.2020.03.050.
Yu Y., Liu A., Dhawan G. et al. Fluorine-containing pharmaceuticals approved by the FDA in 2020: Synthesis and biological activity. Chin. Chem. Lett. 2021. 32(11): 3342–3354.
doi: 10.1016/j.cclet.2021.05.042.
He J., Li Z., Dhawan G. et al. Fluorine-containing drugs approved by the FDA in 2021. Chin. Chem. Lett. 2023. 34(1): 107578.
doi: 10.1016/j.cclet.2022.06.001.
Du Y., Bian Y., Baecker D. et al. Fluorine in the Pharmaceutical Industry: FDA‐Approved Fluorine‐Containing Drugs in 2024. Chem.–Eur. J. 2025. e202500662.
doi.org/10.1002/chem.202500662.
Wang Q., Han J., Sorochinsky A. et al. The Latest FDA-Approved Pharmaceuticals Containing Fragments of Tailor-Made Amino Acids and Fluorine. Pharmaceuticals. 2022. 15(8): 999.
doi.org/10.3390/ ph150809991847558.
Han J., Wzorek A. Dhawan G. et al. New drugs on the pharmaceutical market containing fluorine and residues of tailor-made amino acids. Ukr. Chem. J. 2024. 90(9): 31–56.
doi: 10.33609/2708-129X.90.9.2024.31-56.
Yin Z., Hu W., Zhang W. et al. Tailor-made amino acid-derived pharmaceuticals approved by the FDA in 2019. Amino Acids. 2020. 52(9): 1227–1261.
doi: 10.1007/s00726-020-02887-4.
Liu A., Han J., Nakano A. et al. New pharmaceuticals approved by FDA in 2020: Small-molecule drugs derived from amino acids and related compounds. Chirality. 2022. 34(1): 86–103.
doi: 10.1002/chir.23376.
Wang N., Mei H., Dhawan G. et al. New Approved Drugs Appearing in the Pharmaceutical Market in 2022, Featuring Fragments of Tailor-Made Amino Acids and Fluorine. Molecules. 2023. 28(9): 3651.
doi: 10.3390/molecules28093651.
Han J., Wzorek A., Dhawan G. et al. New drugs appearing on the market in 2023: molecules containing fluorine and fragments of tailor-made amino acids. Ukr. Bioorg. Acta. 2024. 19(1): 3–20.
doi: 10.15407/bioorganica2024.01.003.
Ellis T.K., Hochla V.M., Soloshonok V.A. Efficient synthesis of 2-aminoindane-2-carboxylic acid via dialkylation of nucleophilic glycine equivalent. J. Org. Chem. 2003. 68(12): 4973–4976.
doi.org/10.1021/jo030065v.
Wzorek A., Sorochinsky A.E., Klika K.D. et al. Asymmetric synthesis of chi-constrained glutamic acids and related compounds via Michael addition reactions. Ukr. Chem. J. 2024. 90(8): 83–108.
doi: 10.33609/2708-129X.90.8.2024.83-108.
Han J., Liu H., Wang J. et al. Hamari’s contribution to the asymmetric synthesis of tailor-made amino acids. Ukr. Chem. J. 2024. 90(10): 88–134.
doi: 10.33609/2708-129X.90.10.2024.88-134.
Cai C., Soloshonok V.A., Hruby V.J. Michael Addition Reactions between Chiral Ni(II) Complex of Glycine and 3-(trans-Enoyl)oxazolidin-2-ones. A Case of Electron Donor–Acceptor Attractive Interaction-Controlled Face Diastereoselectivity. J. Org. Chem. 2001. 66(4): 1339–1350.
doi: 10.1021/jo0014865.
Qiu W., Gu X., Soloshonok V.A. et al. Stereoselective synthesis of conformationally constrained reverse turn dipeptide mimetics. Tetrahedron Lett. 2001. 42(2): 145–148.
doi: 10.1016/S0040-4039(00)01864-5.
Lyutenko N.V., Han J., Wzorek A. et al. Carbon nanotubes-catalyzed synthesis of fluorine-containing heterocycles. Ukr. Chem. J. 2024. 90(6): 71–86.
doi: 10.33609/2708-129X.90.6.2024.71-86.
Rizzo C., Amata S., Pibiri I. et al. FDA-approved fluorinated heterocyclic drugs from 2016 to 2022. Int. J. Mol. Sci. 2023. 24(9): 7728. doi.org/10.3390/ijms24097728.
He J., Wang C., Mei H. et al. Visible-light-promoted cyclization of 3-indolylallylamides enabling synthesis of tetrahydrocarbolinones. Tetrahedron. 2024. 150: 133776.
doi.org/10.1016/j.tet.2023.133776.
Du Y., Mei H., Makarem A. et al. Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters. Beilstein J. Org. Chem. 2024. 20(1): 212–219. doi.org/10.3762/bjoc.20.21.
Javahershenas R., Mei H., Koley M. et al. Recent advances in the multicomponent synthesis of heterocycles using 5-aminotetrazole. Synthesis. 2024. 56(16): 2445–2461.
doi: 10.1055/s-0042-1751526.
Abbas A.A., Farghaly T.A., Dawood K.M. Recent progress in therapeutic applications of fluorinated five-membered heterocycles and their benzo-fused systems. RSC Adv. 2024. 14(46): 33864–33905.
doi: 10.1039/D4RA05697C.
Yamada T., Okada T., Sakaguchi K. et al. Efficient asymmetric synthesis of novel 4-substituted and configurationally stable analogues of thalidomide. Org. Lett. 2006. 8(24): 5625–5628. doi: 10.1021/ol0623668.
Takeda R., Kawamura A., Kawashima A. et al. Chemical dynamic kinetic resolution and S/R interconversion of unprotected α‐amino acids. Angew. Chem., Int. Ed. 2014. 53(45): 12214–12217.
doi.org/10.1002/anie.201407944.
Wang Y., Song X., Wang J. et al. Recent approaches for asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes. Amino Acids. 2017. 49(9): 1487–1520.
doi: 10.1007/s00726-017-2458-6.
Nian Y., Wang J., Zhou S. et al. Recyclable ligands for the non‐enzymatic dynamic kinetic resolution of challenging α‐amino acids. Angew. Chem., Int. Ed. 2015. 54(44): 12918–12922. doi.org/10.1002/anie.201507273.
Grygorenko O.O., Volochnyuk D.M., Vashchenko B.V. Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances. Eur. J. Org. Chem. 2021. 2021(47): 6478–6510.
doi.org/10.1002/ejoc.202100857.
Leśniewska A., Przybylski P. Seven-membered N-heterocycles as approved drugs and promising leads in medicinal chemistry as well as the metal-free domino access to their scaffolds. Eur. J. Med. Chem. 2024. 275: 116556.
doi.org/10.1016/j.ejmech.2024.116556.
Kumar N., Goel N. Heterocyclic compounds: importance in anticancer drug discovery. Anticancer Agents Med. Chem. 2022. 22(19): 3196–3207.
doi.org/10.2174/1871520622666220404082648.
Rusu A., Moga I.M., Uncu L., Hancu G. The role of five-membered heterocycles in the molecular structure of antibacterial drugs used in therapy. Pharmaceutics. 2023. 15(11): 2554.
doi.org/10.3390/pharmaceutics15112554.
Al‐Bogami A.S., Saleh T.S., Moussa T.A. Green synthesis, antimicrobial activity and cytotoxicity of novel fused pyrimidine derivatives possessing a trifluoromethyl moiety. ChemistrySelect. 2018. 3(28): 8306–8311.
doi.org/10.1002/slct.201801050.
Howard L., Nicholson W., Sagatov Y., Browne D.L. One-pot multistep mechanochemical synthesis of fluorinated pyrazolones. Beilstein J. Org. Chem. 2017. 13(1): 1950–1956.
doi:10.3762/bjoc.13.189
Yuan D., He Y., Sun X. et al. Recent Advances in the Application of Selectfluor as a Versatile Reactant in Organic Photo‐and Electrochemical Synthesis. Chemistry Select. 2025. 10(7): e202405859.
doi.org/10.1002/slct.202405859.
Soloshonok V.A., Mikami K., Yamazaki T., Welch J.T., Honek J.F. Eds. Current fluoroorganic chemistry: new synthetic directions, technologies, materials, and biological applications. ACS Symposium Series #949; Oxford University Press, 2007.
doi: 10.1021/bk-2007-0949.
Kumar D., Sharma S., Kalra S. et al. Medicinal perspective of indole derivatives: recent developments and structure-activity relationship studies. Curr. Drug Targets. 2020. 21(9): 864–891.
doi.org/10.2174/1389450121666200310115327.
Mo X., Rao D.P., Kaur K. et al. Indole derivatives: a versatile scaffold in modern drug discovery–an updated review on their multifaceted therapeutic applications (2020–2024). Molecules. 2024. 29(19): 4770.
doi.org/10.3390/molecules29194770.
Kaushik N.K., Kaushik N., Attri P. et al. Biomedical importance of indoles. Molecules. 2013. 18(6): 6620–6662.
doi.org/10.3390/molecules18066620.
Kumar S., Ritika. A brief review of the biological potential of indole derivatives. Future J. Pharm. Sci. 2020. 1–9.
doi.org/10.1186/s43094-020-00141-y.
Humphrey G.R., Kuethe J.T. Practical methodologies for the synthesis of indoles. Chem. Rev. 2006. 106(7): 2875–2911.
doi.org/10.1021/cr0505270.
Taber D.F., Tirunahari P.K. Indole synthesis: a review and proposed classification. Tetrahedron. 2011. 67(38): 7195–7210.
doi.org/10.1016/j.tet.2011.06.040.
Gribble G.W. Recent developments in indole ring synthesis–Methodology and applications. Contemp. Org. Synth. 1994. 1(3): 145–172.
doi: 10.1039/CO9940100145.
Wu L., Xie C., Mei H. et al. Asymmetric Friedel–Crafts Reactions of N-tert-Butylsulfinyl-3,3,3-trifluoroacetaldimines: General Access to Enantiomerically Pure Indoles Containing a 1-Amino-2,2,2-trifluoroethyl Group. J. Org. Chem. 2014. 79(16): 7677–7681.
doi.org/10.1021/jo5012009.
Zhu Y., Mao Y., Mei H. et al. Palladium‐Catalyzed Asymmetric Allylic Alkylations of Colby Pro‐Enolates with MBH Carbonates: Enantioselective Access to Quaternary C–F Oxindoles. Chem.—Eur. J. 2018. 24(36): 8994–8998.
doi.org/10.1002/chem.201801670.
Li T., Zhou S., Wang J. et al. Asymmetric synthesis of α-(1-oxoisoindolin-3-yl)glycine: synthetic and mechanistic challenges. Chem. Commun. 2015 51(9): 1624–1626.
doi: 10.1039/C4CC05659K.
Xie C., Zhang L., Sha W. et al. Detrifluoroacetylative in situ generation of free 3-fluoroindolin-2-one-derived tertiary enolates: design, synthesis, and assessment of reactivity toward asymmetric Mannich reactions. Org. Lett. 2016. 18(13): 3270–3273.
doi.org/10.1021/acs.orglett.6b01516.
Xu X., Guo X., Chen Z. et al. Mechanochemical Synthesis of Carbazole Isomer Phosphors. Small. 2025. 21(1): 2405639.
doi.org/10.1002/smll.202405639.
Asif M. Chemical Characteristics, Synthetic Methods, and Biological Potential of Quinazoline and Quinazolinone Derivatives. Int. J. Med. Chem. 2014. 214: 395637.
doi.org/10.1155/2014/395637.
Khan I., Ibrar A., Ahmed W., Saeed A. Synthetic approaches, functionalization and therapeutic potential of quinazoline and quinazolinone skeletons: The advances continue. Eur. J. Med. Chem. 2015. 90: 124–169.
doi.org/10.1016/j.ejmech.2014.10.084.
Imai T., Niijima E., Terada S. et al. Chirality-dependent halogen bonds in axially chiral quinazolin-4-one derivatives bearing ortho-halophenyl groups. CrystEngComm. 2019. 21(22): 3385–3389.
doi: 10.1039/C9CE00320G.
Henary M., Paranjpe S., Owens E.A. Substituted benzothiazoles: synthesis and medicinal characteristics. Heterocycl. Commun. 2013. 19(2): 89–99.
doi.org/10.1515/hc-2013-0026.
Banerjee S., Payra S., Saha A. A review on synthesis of benzothiazole derivatives. Curr. Organocat. 2017. 4(3): 164–181.
doi.org/10.2174/2213337205666180119143539.
Dai Y., Xie C., Wu L. et al. Asymmetric synthesis of amino-benzothiazol derivatives by additions of 2-lithiated benzothiazoles to (S)-N-t-butylsulfinyl-ketimines. RSC Adv. 2015. 5(5): 3491–3497.
doi: 10.1039/c4ra15405c.
Li Z., Wang N., Liu J. et al. Synthesis of Isothiazoles through N-Propargylsulfinylamide: TFA-Promoted Sulfinyl Group-Involved Intramolecular Cyclization. Org. Lett. 2021. 23(17): 6941−6945.
doi.org/10.1021/acs.orglett.1c02538.
Sharma A., Singh J., Sharma A. Synthesis of Quinazolinones and Benzothiazoles Using α-Keto Acids under Ball Milling. J. Org. Chem. 2024. 89(8): 5229–5238.
doi.org/10.1021/acs.joc.3c02435.
Fu L., Wan J.P. C3‐Functionalized Chromones Synthesis by Tandem C–H Elaboration and Chromone Annulation of Enaminones. Asian J. Org. Chem. 2019. 8(6): 767–776.
doi.org/10.1002/ajoc.201900196.
Sharma V., Sharma A., Wadje B.N., Bharate S.B. Benzopyrone, a privileged scaffold in drug discovery: An overview of FDA‐approved drugs and clinical candidates. Med. Res. Rev. 2024. 44(5): 2035–2077.
doi.org/10.1002/med.22032.
Koley M., Han J., Soloshonok V.A. et al. Latest developments in coumarin-based anticancer agents: mechanism of action and structure–activity relationship studies. RSC Med. Chem. 2024. 15(1): 10–54.
doi: 10.1039/d3md00511a.
Mkrtchyan S., Purohit V.B., Khutsishvili S. et al. Mechanochemical Defluorinative Acylation of ortho‐Hydroxyarylenaminones by CF3‐Compounds: Synthesis of 3‐Acylchromones. Adv. Syn. Cat. 2023. 365(12): 2026–2035.
doi.org/10.1002/adsc.202300260.
Wang Q., Zhang X., Sorochinsky A.E. et al. Advances in the development of trifluoromethoxylation reagents. Symmetry. 2021. 13(12): 2380.
doi.org/10.3390/sym13122380.
Liu J., Lin W., Sorochinsky A.E. et al. Successful trifluoromethoxy-containing pharmaceuticals and agrochemicals. J. Fluor. Chem. 2022. 257: 109978.
doi.org/10.1016/j.jfluchem.2022.109978.
Jin M., Song G., Li Z. et al. Efficient Synthesis of 2‐Aryl‐1‐arylmethyl‐1H‐benzimidazoles in Ball Mill without Solvent. J. Heterocycl. Chem. 2014. 51(6): 1838–1843.
doi.org/10.1002/jhet.1113.
Soloshonok V.A., Kirilenko A.G., Kukhar V.P., Resnati G. A practical route to fluoroalkyl-and fluoroarylamines by base-catalyzed [1,3]-proton shift reaction. Tetrahedron Lett. 1994. 35(19): 3119–3122.
doi.org/10.1016/S0040-4039(00)76845-6.
Soloshonok V.A., Hayashi T. Gold(I)-catalyzed asymmetric aldol reaction of fluorinated benzaldehydes with α-isocyanoacetamide. Tetrahedron: Asymmetry. 1994. 5(6): 1091–1094.
doi: 10.1016/0957-4166(94)80059-6.
Soloshonok V.A., Hayashi T. Gold(I)-catalyzed asymmetric aldol reaction of methyl isocyanoacetate with fluorinated benzaldehydes. Tetrahedron Lett. 1994. 35(17): 2713–2716.
doi: 10.1016/S0040-4039(00)77013-4.
Geary G.C., Hope E.G., Stuart A.M. Intramolecular Fluorocyclizations of Unsaturated Carboxylic Acids with a Stable Hypervalent Fluoroiodane Reagent. Angew. Chem., Int. Ed. 2015. 54(49): 14911–14914.
https://doi.org/10.1002/anie.201507790.
Soloshonok V.A., Kacharov A.D., Hayashi T. Gold (I)-catalyzed asymmetric aldol reactions of isocyanoacetic acid derivatives with fluoroaryl aldehydes. Tetrahedron. 1996. 52(1): 245–254.
doi.org/10.1016/0040-4020(95)00893-D.
Zou Y., Han J., Saghyan A.S. et al. Asymmetric Synthesis of Tailor-Made Amino Acids Using Chiral Ni(II) Complexes of Schiff Bases. An Update of the Recent Literature. Molecules. 2020. 25(12): 2739.
doi.org/10.3390/molecules25122739.
Khaligh N.G., Mihankhah T., Johan M.R. Green one-pot multicomponent synthesis of pyrrolidinones using planetary ball milling process under solvent-free conditions. Synthetic Commun. 2019. 49(10): 1334–1342.
doi.org/10.1080/00397911.2019.1601225.
Singh H.K., Kamal A., Maury S.K. et al. A green synthesis of pyrimido [4,5-b] quinolines and pyrido [2,3-d] pyrimidines via a mechanochemical approach. Org. Biomol. Chem. 2023. 21(23): 4854–4862.
doi: 10.1039/d3ob00626c.
Soloshonok V.A., Ohkura H., Yasumoto M. Operationally convenient asymmetric synthesis of (S)- and (R)-3-amino-4,4,4-trifluorobutanoic acid: Part II. Enantioselective biomimetic transamination of 4,4,4-trifluoro-3-oxo-N-[(R)-1-phenylethyl)butanamide. J. Fluor. Chem. 2006. 127(7): 930–935.
doi: 10.1016/j.jfluchem.2006.04.004.
Shibata N., Nishimine T., Shibata N. et al. Organic base-catalyzed stereodivergent synthesis of (R)- and (S)-3-amino-4,4,4-trifluorobutanoic acids. Chem. Commun. 2012. 48: 4124–4126.
doi:10.1039/C2CC30627A.
Soloshonok V.A., Kirilenko A.G., Kukhar V.P., Resnati G. Transamination of fluorinated β-keto carboxylic esters. A biomimetic approach to β-polyfluoroalkyl-β-amino acids. Tetrahedron Lett. 1993. 34(22): 3621–3624.
doi.org/10.1016/S0040-4039(00)73652-5.
Shahid A., Ahmed N.S., Saleh T.S. et al. Solvent-free Biginelli reactions catalyzed by hierarchical zeolite utilizing a ball mill technique: A green sustainable process. Catalysts. 2017. 7(3): 84.
doi.org/10.3390/catal7030084.
Chandravarkar A., Aneeja T., Anilkumar G. Advances in Biginelli reaction: A comprehensive review. J. Heterocycl. Chem. 2024. 61(1): 5–28.
doi.org/10.1002/jhet.4742.
Dekamin M.G., Alikhani M., Javanshir S. Organocatalytic clean synthesis of densely functionalized 4H-pyrans by bifunctional tetraethylammonium 2-(carbamoyl) benzoate using ball milling technique under mild conditions. Green Chem. Lett. Rev. 2016. 9(2): 96–105.
doi.org/10.1080/17518253.2016.1139191.
Krauskopf F., Truong K.N., Rissanen K., Bolm C. 2,3-Dihydro-1,2,6-thiadiazine 1-
Oxides by Biginelli-Type Reactions with Sulfonimidamides under Mechanochemical Conditions. Org. Lett. 2021. 23(7): 2699–2703.
doi.org/10.1021/acs.orglett.1c00596.
Mallah D., Mirjalili B.B. A green protocol ball milling synthesis of dihydropyrano [2, 3-c] pyrazole using nano-silica/aminoethylpiperazine as a metal-free catalyst. BMC Chem. 2023. 17(1): 10.
doi.org/10.1186/s13065-023-00934-1.
Dekamin M.G., Alikhani M., Emami A. et al. An efficient catalyst- and solvent-free method for the synthesis of medicinally important dihydropyrano [2,3-c]pyrazole derivatives using ball milling technique. J. Iran. Chem. Soc. 2016. 13(3): 591–596.
doi.org/10.1007/s13738-015-0793-7.
Ohkura H., Berbasov D.O., Soloshonok V.A. Chemo-and regioselectivity in the reactions between highly electrophilic fluorine containing dicarbonyl compounds and amines. Improved synthesis of the corresponding imines/enamines. Tetrahedron. 2003. 59(10): 1647–1656.
doi.org/10.1016/S0040-4020(03)00138-8.
Bravo P., Guidetti M., Viani F. et al. Chiral sulfoxide controlled asymmetric additions to C N double bond. An efficient approach to stereochemically defined α-fluoroalkyl amino compounds. Tetrahedron. 1998. 54(42): 12789–12806.
doi: 10.1016/S0040-4020(98)00779-0.
Xie C., Wu L., Mei H. et al. Generalized access to fluorinated β-keto amino compounds through asymmetric additions of α,α-difluoroenolates to CF3-sulfinylimine. Org. Biomol. Chem. 2014. 12(39): 7836–7843.
doi: 10.1039/C4OB01575D.
Guha S., Sen S., Gremaud L. Eco-friendly anaerobic oxidation of aryl diazo esters with heterocyclic N-oxide under ball milling: synthesis of 1,2-dicarbonyl systems. RSC Mechanochem. 2025. 2(1): 45–53.
doi: 10.1039/D4MR00097H
Kudličková Z., Stahorský M., Michalková R. et al. Mechanochemical synthesis of indolyl chalcones with antiproliferative activity. Green Chem. Lett. Rev. 2022. 15(2): 474–482.
doi.org/10.1080/17518253.2022.2089061.
Liu X.W., Wang J.Q., Ma H. et al. Ball-milling synthesis of sulfonyl quinolines via coupling of haloquinolines with sulfonic acids. Green Chem. 2021. 23(19): 7589–7593.
doi: 10.1039/D1GC02015C.
Roy S., Gregg B.T., Gribble G.W. et al. Trifluoromethylation of aryl and heteroaryl halides. Tetrahedron. 2011. 67(12): 2161–2195.
doi.org/10.1016/j.tet.2011.01.002.
Zhu W., Wang J., Wang S. et al. Recent advances in the trifluoromethylation methodology and new CF3-containing drugs. J. Fluor. Chem. 2014. 167: 37–54.
doi: 10.1016/j.jfluchem.2014.06.026.
Sato A., Han J., Ono T. et al. Introducing a new radical trifluoromethylation reagent. Chem. Commun. 2015. 51(27): 5967–5970.
doi: 10.1039/c5cc00905g.
Pang Y., Lee J.W., Kubota K., Ito H. Solid‐State Radical C− H Trifluoromethylation Reactions Using Ball Milling and Piezoelectric Materials. Angew. Chem., Int. Ed. 2020. 59(50): 22570–22576.
doi.org/10.1002/anie.202009844.
Umemoto T. Electrophilic perfluoroalkylating agents. Chem. Rev. 1996. 96(5): 1757–1778.
doi.org/10.1021/cr941149u.
Tireli M., Maračić S., Lukin S. et al. Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole. Beilstein J. Org. Chem. 2017. 13(1): 2352–2363.
doi.org/10.3762/bjoc.13.232.
Jörres M., Aceña J.L., Soloshonok V.A., Bolm C. Asymmetric Carbon-Carbon Bond Formations under Solvent-Less Conditions in Ball Mills. ChemCatChem. 2015. 7: 1265–1269;
doi: 10.1002/cctc.201500102.
Moore J.L., Taylor S.M., Soloshonok V.A. An efficient and operationally convenient general synthesis of tertiary amines by direct alkylation of secondary amines with alkyl halides in the presence of Huenig’s base. Arkivoc. 2005. 6(iv): 287–292.
doi.org/10.3998/ark.5550190.0006.624.