Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways

Scholarly Works

• Zavalinich, V. A.; Elek, G. Z.; Vailhé, P.; Novikau, I.; Syakhovich, V.; Kirillov, A. M.; Lopp, M.; Masiuk, U. S.; Kananovich, D. G. Ligand‐Tailored Divergence of Copper‐Catalyzed Aerobic Oxidation of Cyclopropanols. Application to the Practical Synthesis of β‐Aminoketones and β‐Enaminones. Advanced Synthesis & Catalysis 2024. doi:10.1002/adsc.202400490
• Xie, Y.; Huang, W.; Qin, S.; Fu, S.; Liu, B. Catalytic radical cascade cyclization of alkene-tethered enones to fused bicyclic cyclopropanols. Organic Chemistry Frontiers 2021, 8, 6678–6686. doi:10.1039/d1qo01312b
• Yuan, S.; Zhang, J.-Y.; Zhang, D.-Q.; Wei, D.; Zuo, J.-H.; Song, J.; Yu, B.; Liu, H.-M. Cu(OTf)2-Catalyzed Intramolecular Radical Cascade Reactions for the Diversity-Oriented Synthesis of Quinoline-Annulated Polyheterocyclic Frameworks. Organic letters 2021, 23, 1445–1450. doi:10.1021/acs.orglett.1c00129
• McDonald, T. R.; Mills, L. R.; West, M. S.; Rousseaux, S. A. L. Selective Carbon–Carbon Bond Cleavage of Cyclopropanols. Chemical reviews 2020, 121, 3–79. doi:10.1021/acs.chemrev.0c00346
• Wu, L.; Wang, L.; Chen, P.; Guo, Y.; Liu, G. Enantioselective Copper-Catalyzed Radical Ring-Opening Cyanation of Cyclopropanols and Cyclopropanone Acetals. Advanced Synthesis & Catalysis 2020, 362, 2189–2194. doi:10.1002/adsc.202000202
• Liu, J.; Xu, E.; Jiang, J.; Huang, Z.; Zheng, L.; Liu, Z.-Q. Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: synthesis of N-arylpyrazoles. Chemical communications (Cambridge, England) 2020, 56, 2202–2205. doi:10.1039/c9cc09657d
• McKenzie, S. G.; Palluccio, T. D.; Patterson, J. D.; Rybak-Akimova, E. V. Synthesis, characterization, and oxidation catalysis studies of a monofunctionalized copper pyridine-aza macrocycle. Inorganica Chimica Acta 2018, 482, 732–737. doi:10.1016/j.ica.2018.07.008
• Ye, Z.; Cai, X.; Li, J.; Dai, M. Catalytic Cyclopropanol Ring Opening for Divergent Syntheses of γ-Butyrolactones and δ-Ketoesters Containing All-Carbon Quaternary Centers. ACS catalysis 2018, 8, 5907–5914. doi:10.1021/acscatal.8b00711
• Konik, Y. A.; Elek, G. Z.; Kaabel, S.; Järving, I.; Lopp, M.; Kananovich, D. G. Synthesis of γ-keto sulfones by copper-catalyzed oxidative sulfonylation of tertiary cyclopropanols. Organic & biomolecular chemistry 2017, 15, 8334–8340. doi:10.1039/c7ob01605k
• Tumma, N.; Gyanchander, E.; Kun, J. Cu-Mediated Rearrangements of Allenylcyclopropanols to Cyclopentenones: Two Divergent Pathways. The Journal of organic chemistry 2017, 82, 4379–4385. doi:10.1021/acs.joc.7b00432
• Davis, D. C.; Haskins, C. W.; Dai, M. Radical Cyclopropanol Ring Opening Initiated Tandem Cyclizations for Efficient Synthesis of Phenanthridines and Oxindoles. Synlett : accounts and rapid communications in synthetic organic chemistry 2017, 28, 913–918. doi:10.1055/s-0036-1588929
• Hasegawa, E.; Nemoto, K.; Nagumo, R.; Tayama, E.; Iwamoto, H. Solvent-Dependent Reaction Pathways Operating in Copper(II) Tetrafluoroborate Promoted Oxidative Ring-Opening Reactions of Cyclopropyl Silyl Ethers. The Journal of organic chemistry 2016, 81, 2692–2703. doi:10.1021/acs.joc.5b02827
• Ye, Z.; Gettys, K. E.; Shen, X.; Dai, M. Copper-Catalyzed Cyclopropanol Ring Opening Csp3–Csp3 Cross-Couplings with (Fluoro)Alkyl Halides. Organic letters 2015, 17, 6074–6077. doi:10.1021/acs.orglett.5b03096
• Li, Y.; Ye, Z.; Bellman, T. M.; Chi, T.; Dai, M. Efficient Synthesis of β-CF3/SCF3 Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols. Organic letters 2015, 17, 2186–2189. doi:10.1021/acs.orglett.5b00782
• Ye, Z.; Dai, M. An Umpolung Strategy for the Synthesis of β-Aminoketones via Copper-Catalyzed Electrophilic Amination of Cyclopropanols. Organic letters 2015, 17, 2190–2193. doi:10.1021/acs.orglett.5b00828

Explore citations to this article at