Gold-catalyzed propargylic substitutions: Scope and synthetic developments

Scholarly Works

• Doraghi, F.; Mohammad Mahdavian, A.; Karimian, S.; Larijani, B.; Mahdavi, M. Recent Progress in Application of Propargylic Alcohols in Organic Syntheses. Advanced Synthesis & Catalysis 2023, 365, 2991–3019. doi:10.1002/adsc.202300646
• Bera, N.; Lenka, B. S.; Bishi, S.; Samanta, S.; Sarkar, D. Gold(I)-Catalyzed Synthesis of Heterocycles via Allene Oxide from Propargylic Alcohols. The Journal of organic chemistry 2022, 87, 9729–9754. doi:10.1021/acs.joc.2c00780
• Jónsson, H. F.; Solvi, T. N.; Lomeland, S.; Reiersølmoen, A. C.; Fiksdahl, A. Tunable Gold-catalyzed Reactions of Propargyl Alcohols and Aryl Nucleophiles. ChemistryOpen 2022, 11, e202200030. doi:10.1002/open.202200030
• Cordero, F. M.; Giomi, D.; Machetti, F. 4.03 – Isoxazoles. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; Vol. 4, pp 308–434. doi:10.1016/b978-0-12-818655-8.00135-9
• Morita, N.; Tamura, O. Strategic Use of Difference of Valence of Gold Catalysts: Development of Cyclization Reactions Oriented toward Synthetic Diversity Using Propargylic Alcohols. Journal of Synthetic Organic Chemistry, Japan 2021, 79, 652–663. doi:10.5059/yukigoseikyokaishi.79.652
• Zhang, S.; Li, L.; Li, J.; Shi, J.; Xu, K.; Gao, W.; Zong, L.; Li, G.; Findlater, M. Electrochemical Arylation of Aldehydes, Ketones, and Alcohols: from Cathodic Reduction to Convergent Paired Electrolysis. Angewandte Chemie (International ed. in English) 2021, 60, 7275–7282. doi:10.1002/anie.202015230
• Zhang, S.; Li, L.; Li, J.; Shi, J.; Xu, K.; Gao, W.; Zong, L.; Li, G.; Findlater, M. Electrochemical Arylation of Aldehydes, Ketones, and Alcohols: from Cathodic Reduction to Convergent Paired Electrolysis. Angewandte Chemie 2021, 133, 7351–7358. doi:10.1002/ange.202015230
• Tsuji, H.; Kawatsura, M. Transition‐Metal‐Catalyzed Propargylic Substitution of Propargylic Alcohol Derivatives Bearing an Internal Alkyne Group. Asian Journal of Organic Chemistry 2020, 9, 1924–1941. doi:10.1002/ajoc.202000422
• Pradhan, T. R.; Park, J. K. An Overview of Water‐Mediated Alkyne Functionalization by Neighboring Group Participation of Carbonyl Groups. Advanced Synthesis & Catalysis 2020, 362, 4833–4860. doi:10.1002/adsc.202000826
• Oseghale, C. O.; Mogudi, B. M.; Akinnawo, C. A.; Meijboom, R. in-situ generation of surface-active HCo(CO)y like intermediate from gold supported on ion-promoted Co3O4 for induced hydroformylation-hydrogenation of alkenes to alcohols. Applied Catalysis A: General 2020, 602, 117735. doi:10.1016/j.apcata.2020.117735
• Noël, F.; Vuković, V. D.; Yi, J.; Richmond, E.; Kravljanac, P.; Moran, J. Catalytic Synthesis of Trifluoromethylated Allenes, Indenes, Chromenes, and Olefins from Propargylic Alcohols in HFIP. The Journal of organic chemistry 2019, 84, 15926–15947. doi:10.1021/acs.joc.9b02398
• Schmidt, E. Y.; Bidusenko, I. A.; Protsuk, N. I.; Demyanov, Y. V.; Ushakov, I. A.; Trofimov, B. A. Superbase-Promoted Addition of Acetylene Gas to the C=N Bond. European Journal of Organic Chemistry 2019, 2019, 5875–5881. doi:10.1002/ejoc.201900932
• Miao, C.; Zhuang, H.; Wen, Y.; Han, F.; Yang, Q.-F.; Yang, L.; Li, Z.; Xia, C. Efficient Thiolation of Alcohols Catalyzed by Long Chained Acid-Functionalized Ionic Liquids under Mild Conditions. European Journal of Organic Chemistry 2019, 2019, 3012–3021. doi:10.1002/ejoc.201900169
• Praveen, C. Dexterity of gold catalysis in controlling the regioselectivity of cycloaddition reactions. Catalysis Reviews 2019, 61, 406–446. doi:10.1080/01614940.2019.1594016
• Alyabyev, S. B.; Beletskaya, I. P. Gold as a catalyst. Part II. Alkynes in the reactions of carbon – carbon bond formation. Russian Chemical Reviews 2018, 87, 984–1047. doi:10.1070/rcr4815
• Roy, R.; Saha, S. Scope and advances in the catalytic propargylic substitution reaction. RSC advances 2018, 8, 31129–31193. doi:10.1039/c8ra04481c
• Iwasawa, N.; Watanabe, S.; Ario, A.; Sogo, H. Re(I)-Catalyzed Hydropropargylation of Silyl Enol Ethers Utilizing Dynamic Interconversion of Vinylidene-Alkenylmetal Intermediates via 1,5-Hydride Transfer. Journal of the American Chemical Society 2018, 140, 7769–7772. doi:10.1021/jacs.8b02903
• Brandi, A.; Cardona, F.; Cicchi, S.; Cordero, F. M.; Goti, A. Organic Reactions; Wiley, 2017; pp 1–321. doi:10.1002/0471264180.or094.01
• Shan, C.; Chen, F.; Pan, J.; Gao, Y.; Xu, P.; Zhao, Y. Zn(OTf)2-Catalyzed Phosphinylation of Propargylic Alcohols: Access to γ-Ketophosphine Oxides. The Journal of organic chemistry 2017, 82, 11659–11666. doi:10.1021/acs.joc.7b02164
• Zhang, K.; Lu, L.-Q.; Yao, S.; Chen, J.-R.; Shi, D.-Q.; Xiao, W.-J. Enantioconvergent Copper Catalysis: In Situ Generation of the Chiral Phosphorus Ylide and Its Wittig Reactions. Journal of the American Chemical Society 2017, 139, 12847–12854. doi:10.1021/jacs.7b08207

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