Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives

Scholarly Works

• Miguélez, R.; Arto, O.; Semleit, N.; Haberhauer, G.; Barrio, P. Electronic and Steric Effects in a Gold(I)‐Catalyzed Intramolecular C(sp3)−H Bond Activation Reaction of 1‐Bromoalkynes. Advanced Synthesis & Catalysis 2024, 366, 780–789. doi:10.1002/adsc.202301191
• Ghosh, T.; Chatterjee, J.; Bhakta, S. Gold-catalyzed hydroarylation reactions: a comprehensive overview. Organic & biomolecular chemistry 2022, 20, 7151–7187. doi:10.1039/d2ob00960a
• Fernández-Canelas, P.; Miguélez, R.; Rubio, E.; González, J. M.; Barrio, P. Intramolecular activation of strong Si-O bonds by gold(I): regioselective synthesis of 3-bromo-2-silylbenzofurans. Chemical communications (Cambridge, England) 2022, 58, 9250–9253. doi:10.1039/d2cc03060h
• Fernández-Canelas, P.; Barrio, P.; González, J. M. Merging gold catalysis and haloethynyl frames: Emphasis on halide-shift processes. Tetrahedron Letters 2022, 99, 153857. doi:10.1016/j.tetlet.2022.153857
• Baire, B.; Yadav, B. TfOH catalysed domino-double annulation of arenes with propargylic alcohols: a unified approach to indene polycyclic systems. Chemical communications (Cambridge, England) 2021, 57, 12796–12799. doi:10.1039/d1cc05253e
• Velasco, N.; Suárez, A.; Martínez-Lara, F.; Fernández-Rodríguez, M. A.; Sanz, R.; Suárez-Pantiga, S. From Propargylic Alcohols to Substituted Thiochromenes: gem-Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation. The Journal of organic chemistry 2021, 86, 7078–7091. doi:10.1021/acs.joc.1c00333
• Arcadi, A.; Fabrizi, G.; Fochetti, A.; Franzini, R.; Ghirga, F.; Goggiamani, A.; Iazzetti, A.; Marrone, F.; Serraiocco, A. Synthesis of Polycyclic Chromene Cores through Gold (I)-Catalyzed Intramolecular Hydroarylation Reaction (IMHA). European Journal of Organic Chemistry 2021, 2021, 1676–1687. doi:10.1002/ejoc.202100092
• Nakamura, Y.; Sakata, Y.; Hosoya, T.; Yoshida, S. Synthesis of Functionalized Benzopyran/Coumarin-Derived Aryne Precursors and Their Applications. Organic letters 2020, 22, 8505–8510. doi:10.1021/acs.orglett.0c03106
• Mutoh, Y.; Ishii, Y.; Saito, S. Direct formation of disubstituted vinylidenes from internal alkynes at group 8 metal complexes and its application to organic synthesis. Journal of Synthetic Organic Chemistry, Japan 2020, 78, 691–702. doi:10.5059/yukigoseikyokaishi.78.691
• Cadierno, V. Metal-Catalyzed Hydrofunctionalization Reactions of Haloalkynes. European Journal of Inorganic Chemistry 2019, 2020, 886–898. doi:10.1002/ejic.201901016
• Saeed, A.; Shehzadi, S. A.; Bolte, M.; Franca, C. A.; Erben, M. F. Interplay between conformation and crystal packing in aryl propargyl ethers: Structural and spectroscopic properties of 2-(prop-2-yn-1-yloxy)acene derivatives. ChemistrySelect 2019, 4, 9927–9933. doi:10.1002/slct.201902506
• Murai, M.; Takai, K. Rhenium-Catalyzed Cyclization via 1,2-Iodine and 1,5-Hydrogen Migration for the Synthesis of 2-Iodo-1H-indenes. Organic letters 2019, 21, 6756–6760. doi:10.1021/acs.orglett.9b02380
• Roh, S. W.; Choi, K.; Lee, C. Transition Metal Vinylidene- and Allenylidene-Mediated Catalysis in Organic Synthesis. Chemical reviews 2019, 119, 4293–4356. doi:10.1021/acs.chemrev.8b00568
• Hosseinian, A.; Ahmadi, S.; Mohammadi, R.; Didehban, K.; Vessally, E. A Facile and Promising Synthetic Strategy toward Functionalized 2H-Chromenes from Aryl Propargyl Ethers. A Review. Organic Preparations and Procedures International 2018, 50, 544–564. doi:10.1080/00304948.2018.1537306
• Zhang, Q.-C.; Zhang, W.-W.; Shen, L.; Shen, Z.-L.; Loh, T.-P. In(III)-TMSBr-Catalyzed Cascade Reaction of Diarylalkynes with Acrylates for the Synthesis of Aryldihydronaphthalene Derivatives. Molecules (Basel, Switzerland) 2018, 23, 979. doi:10.3390/molecules23040979
• Kirillova, M. S.; Miloserdov, F. M.; Echavarren, A. M. Catalytic Hydroarylation of Carbon‐Carbon Multiple Bonds; Wiley, 2017; pp 217–303. doi:10.1002/9783527697649.ch7
• Echavarren, A. M.; Muratore, M. E.; López-Carrillo, V.; Escribano-Cuesta, A.; Huguet, N.; Obradors, C. Organic Reactions - Gold‐Catalyzed Cyclizations of Alkynes with Alkenes and Arenes. Organic Reactions 2017, 1–288. doi:10.1002/0471264180.or092.01
• Yu, C.; Ma, X.; Chen, B.; Tang, B.; Paton, R. S.; Zhang, G. Dual Gold-Catalyzed Three-Component Reaction: Efficient Synthesis of Indene-Fused Esters, Acids, and Lactones through Gold Vinylidene Intermediates. European Journal of Organic Chemistry 2017, 2017, 1561–1565. doi:10.1002/ejoc.201700084
• Alonso-Marañón, L.; Sarandeses, L. A.; Martínez, M. M.; Sestelo, J. P. Sequential In-catalyzed intramolecular hydroarylation and Pd-catalyzed cross-coupling reactions using bromopropargyl aryl ethers and amines. Organic Chemistry Frontiers 2017, 4, 500–505. doi:10.1039/c6qo00721j
• Sharif, S. A. I.; Calder, E. D. D.; Harkiss, A. H.; Maduro, M.; Sutherland, A. Synthesis of Allylic Amide Functionalized 2H-Chromenes and Coumarins Using a One-Pot Overman Rearrangement and Gold(I)-Catalyzed Hydroarylation. The Journal of organic chemistry 2016, 81, 9810–9819. doi:10.1021/acs.joc.6b01881

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