Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions

Scholarly Works

• Poier, D.; Akl, D. F.; Lucas, E.; Machado, A. R.; Giannakakis, G.; Mitchell, S.; Guillén-Gosálbez, G.; Marti, R.; Pérez-Ramírez, J. Reaction Environment Design for Multigram Synthesis via Sonogashira Coupling over Heterogeneous Palladium Single-Atom Catalysts. ACS sustainable chemistry & engineering 2023, 11, 16935–16945. doi:10.1021/acssuschemeng.3c04183
• Palladino, C.; Fantoni, T.; Ferrazzano, L.; Muzzi, B.; Ricci, A.; Tolomelli, A.; Cabri, W. New Mechanistic Insights into the Copper-Free Heck–Cassar–Sonogashira Cross-Coupling Reaction. ACS Catalysis 2023, 13, 12048–12061. doi:10.1021/acscatal.3c02787
• Fantoni, T.; Tolomelli, A.; Cabri, W. A translation of the twelve principles of green chemistry to guide the development of cross-coupling reactions. Catalysis Today 2022, 397-399, 265–271. doi:10.1016/j.cattod.2021.09.022
• Escalante, C. H.; Carmona-Hernández, F. A.; Hernández-López, A.; Martínez-Mora, E. I.; Reyes, F. D.; Tamariz, J. Cascade synthesis of indolizines and pyrrolo[1,2-a]pyrazines from 2-formyl-1-propargylpyrroles. Organic & biomolecular chemistry 2022, 20, 396–409. doi:10.1039/d1ob01839f
• Chernyshev, V. M.; Khazipov, O. V.; Eremin, D. B.; Denisova, E. A.; Ananikov, V. P. Formation and stabilization of nanosized Pd particles in catalytic systems: Ionic nitrogen compounds as catalytic promoters and stabilizers of nanoparticles. Coordination Chemistry Reviews 2021, 437, 213860. doi:10.1016/j.ccr.2021.213860
• Fantoni, T.; Bernardoni, S.; Mattellone, A.; Martelli, G.; Ferrazzano, L.; Cantelmi, P.; Corbisiero, D.; Tolomelli, A.; Cabri, W.; Vacondio, F.; Ferlenghi, F.; Mor, M.; Ricci, A. Palladium Catalyst Recycling for Heck-Cassar-Sonogashira Cross-Coupling Reactions in Green Solvent/Base Blend. ChemSusChem 2021, 14, 2591–2600. doi:10.1002/cssc.202100623
• Conlon, T. M.; John-Schuster, G.; Heide, D.; Pfister, D.; Lehmann, M.; Hu, Y.; Ertüz, Z.; Lopez, M. A.; Ansari, M.; Strunz, M.; Mayr, C.; Ciminieri, C.; Costa, R.; Kohlhepp, M.; Guillot, A.; Gunes, G.; Jeridi, A.; Funk, M. C.; Beroshvili, G.; Prokosch, S.; Hetzer, J.; Verleden, S. E.; Alsafadi, H. N.; Lindner, M.; Burgstaller, G.; Becker, L.; Irmler, M.; Dudek, M.; Janzen, J.; Goffin, E.; Gosens, R.; Knolle, P. A.; Pirotte, B.; Stoeger, T.; Beckers, J.; Wagner, D. E.; Singh, I.; Theis, F. J.; de Angelis, M. H.; O'Connor, T.; Tacke, F.; Boutros, M.; Dejardin, E.; Eickelberg, O.; Schiller, H. B.; Königshoff, M.; Heikenwalder, M.; Yildirim, A. Ö. Inhibition of LTβR signalling activates WNT-induced regeneration in lung. Nature 2020, 588, 151–156. doi:10.1038/s41586-020-2882-8
• Neofotistos, S. P.; Tzouras, N. V.; Pauze, M.; Gómez-Bengoa, E.; Vougioukalakis, G. C. Manganese-Catalyzed Multicomponent Synthesis of Tetrasubstituted Propargylamines: System Development and Theoretical Study. Advanced Synthesis & Catalysis 2020, 362, 3872–3885. doi:10.1002/adsc.202000566
• Ferrazzano, L.; Martelli, G.; Fantoni, T.; Daka, A.; Corbisiero, D.; Viola, A.; Ricci, A.; Cabri, W.; Tolomelli, A. Fast Heck-Cassar-Sonogashira (HCS) Reactions in Green Solvents. Organic letters 2020, 22, 3969–3973. doi:10.1021/acs.orglett.0c01269
• Idris, M. A.; Lee, S. Recent Advances in Decarboxylative Reactions of Alkynoic Acids. Synthesis 2020, 52, 2277–2298. doi:10.1055/s-0040-1707600
• Prabhala, P.; Savanur, H. M.; Kalkhambkar, R. G.; Laali, K. K. Facile Access to Diverse Libraries of Internal Alkynes via Sequential Iododediazoniation/Decarboxylative Sonogashira Reaction in Imidazolium ILs without Ligand or Additive. European Journal of Organic Chemistry 2019, 2019, 2061–2064. doi:10.1002/ejoc.201900093
• Maaliki, C.; Chevalier, Y.; Thiery, E.; Thibonnet, J. Palladium and copper catalyzed Sonogashira decarboxylative coupling of aryl iodides and alkynyl carboxylic acids. Tetrahedron Letters 2016, 57, 3358–3362. doi:10.1016/j.tetlet.2016.06.073
• Basceken, S.; Kaya, S.; Balci, M. Intramolecular Gold-Catalyzed and NaH-Supported Cyclization Reactions of N-Propargyl Indole Derivatives with Pyrazole and Pyrrole Rings: Synthesis of Pyrazolodiazepinoindole, Pyrazolopyrazinoindole, and Pyrrolopyrazinoindole. The Journal of organic chemistry 2015, 80, 12552–12561. doi:10.1021/acs.joc.5b02419.s001
• Vatansever, E. C.; Kılıç, K.; Ozer, M. S.; Koza, G.; Menges, N.; Balci, M. Intermolecular heterocyclization of alkynones with 2-mercaptoacetaldehyde under metal-free conditions: synthesis of 2,3-disubstituted thiophenes. Tetrahedron Letters 2015, 56, 5386–5389. doi:10.1016/j.tetlet.2015.07.090
• Taskaya; Menges, N.; Balci, M. Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products. Beilstein journal of organic chemistry 2015, 11, 897–905. doi:10.3762/bjoc.11.101
• Guven, S.; Ozer, M. S.; Kaya, S.; Menges, N.; Balci, M. Gold-catalyzed oxime-oxime rearrangement. Organic letters 2015, 17, 2660–2663. doi:10.1021/acs.orglett.5b01041
• Basceken, S.; Balci, M. Design of pyrazolo-pyrrolo-pyrazines and pyrazolo-pyrrolo-diazepines via AuCl₃-catalyzed and NaH-supported cyclization of N-propargyl pyrazoles. The Journal of organic chemistry 2015, 80, 3806–3814. doi:10.1021/acs.joc.5b00034
• Keskin, S.; Balci, M. Intramolecular Heterocyclization of O-Propargylated Aromatic Hydroxyaldehydes as an Expedient Route to Substituted Chromenopyridines under Metal-Free Conditions. Organic letters 2015, 17, 964–967. doi:10.1021/acs.orglett.5b00067
• Jadhav, S.; Kumbhar, A.; Mali, S. S.; Hong, C. K.; Salunkhe, R. A Merrifield resin supported Pd–NHC complex with a spacer(Pd–NHC@SP–PS) for the Sonogashira coupling reaction under copper- and solvent-free conditions. New Journal of Chemistry 2015, 39, 2333–2341. doi:10.1039/c4nj02025a
• Patil, P. H.; Fernandes, R. A. Unimolecular tetrakis-piperidine-4-ol: an efficient ligand for copper and amine free Sonogashira coupling. RSC Advances 2015, 5, 54037–54045. doi:10.1039/c5ra07754k

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