Cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst

Nathan J. Gesmundo and David A. Nicewicz
Beilstein J. Org. Chem. 2014, 10, 1272–1281. https://doi.org/10.3762/bjoc.10.128

Supporting Information

Supporting Information File 1: Experimental procedures and characterization data.
Format: PDF Size: 2.8 MB Download
Supporting Information File 2: X-ray data.
Format: PDF Size: 407.4 KB Download

Cite the Following Article

Cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst
Nathan J. Gesmundo and David A. Nicewicz
Beilstein J. Org. Chem. 2014, 10, 1272–1281. https://doi.org/10.3762/bjoc.10.128

How to Cite

Gesmundo, N. J.; Nicewicz, D. A. Beilstein J. Org. Chem. 2014, 10, 1272–1281. doi:10.3762/bjoc.10.128

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Zhu, X.; Han, J.; Chen, Z.; Shi, Z.; Zhang, J.; Guo, S. Construction of a tunable pyrylium based porous ionic polymer network for efficient waterborne pollutant treatment. Green Chemistry 2024. doi:10.1039/d3gc04737g
  • Galan, N. J.; Cobbold, B. E.; Cromer, C. E.; Brantley, J. N. Macromolecular Photoediting Using Single-Electron Logic. ACS macro letters 2023, 12, 1623–1628. doi:10.1021/acsmacrolett.3c00646
  • Kelch, R. M.; Whyte, A.; Lee, E.; Yoon, T. P. Investigating the Effect of Lewis Acid Co-catalysts on Photosensitized Visible-Light De Mayo Reactions. Organic letters 2023, 25, 4098–4102. doi:10.1021/acs.orglett.3c01321
  • Brambilla, E.; Moretti, E.; Magni, M.; Abbiati, G.; Pirovano, V. Synthesis of tetrahydrocarbazoles through a radical cation [4+2] cycloaddition reaction of 2-vinylindoles. Chemical communications (Cambridge, England) 2023, 59, 3281–3284. doi:10.1039/d2cc06723d
  • Cuadros, S.; Bortolato, T.; Vega-Peñaloza, A.; Dell'Amico, L. Modern Photocatalytic Strategies in Natural Product Synthesis. Progress in the chemistry of organic natural products 2023, 120, 1–104. doi:10.1007/978-3-031-11783-1_1
  • Sureshkumar, D.; Ghosh, K. G.; Pal, K.; Das, D.; Chandu, P. Visible-Light-Mediated Organophotocatalyzed C(sp3)–H Activation and Intramolecular Cyclization. Synlett 2022, 34, 931–936. doi:10.1055/a-1951-9897
  • Bao, L.; Cheng, J.-T.; Wang, Z.-X.; Chen, X.-Y. Pyrylium salts acting as both energy transfer and electron transfer photocatalysts for E → Z isomerization of activated alkenes and cyclization of cinnamic or biaryl carboxylic acids. Organic Chemistry Frontiers 2022, 9, 973–978. doi:10.1039/d1qo01623g
  • Dong, J.; Yue, F.; Liu, J.; Song, H.; Liu, Y.; Wang, Q. Visible-light-mediated three-component Minisci reaction for heteroarylethyl alcohols synthesis. Green Chemistry 2021, 23, 7963–7968. doi:10.1039/d1gc02807c
  • Pitre, S. P.; Overman, L. E. Strategic Use of Visible-Light Photoredox Catalysis in Natural Product Synthesis. Chemical reviews 2021, 122, 1717–1751. doi:10.1021/acs.chemrev.1c00247
  • Yang, X.; Murphy, L. M.; Haque, F. M.; Grayson, S. M.; Boydston, A. J. A highly efficient metal-free protocol for the synthesis of linear polydicyclopentadiene. Polymer Chemistry 2021, 12, 2860–2867. doi:10.1039/d1py00191d
  • Hola, E.; Ortyl, J. Pyrylium salt as a visible-light-induced photoredox catalyst for polymer and organic synthesis – Perspectives on catalyst design and performance. European Polymer Journal 2021, 150, 110365. doi:10.1016/j.eurpolymj.2021.110365
  • George, J. H. Biomimetic Dearomatization Strategies in the Total Synthesis of Meroterpenoid Natural Products. Accounts of chemical research 2021, 54, 1843–1855. doi:10.1021/acs.accounts.1c00019
  • Pokhriyal, A.; Karki, B. S.; Kant, R.; Rastogi, N. Redox-Neutral 1,3-Dipolar Cycloaddition of 2H-Azirines with 2,4,6-Triarylpyrylium Salts under Visible Light Irradiation. The Journal of organic chemistry 2021, 86, 4661–4670. doi:10.1021/acs.joc.1c00082
  • Ferrié, L. Advances in the synthesis of 1,2-dioxolanes and 1,2-dioxanes. Advances in Heterocyclic Chemistry; Elsevier, 2021; Vol. 135, pp 57–146. doi:10.1016/bs.aihch.2021.03.001
  • Mateus-Ruiz, J. B.; Cordero-Vargas, A. Visible-Light-Mediated Photoredox Reactions in the Total Synthesis of Natural Products. Synthesis 2020, 52, 3111–3128. doi:10.1055/s-0040-1707225
  • Budde, S.; Goerdeler, F.; Floß, J.; Kreitmeier, P.; Hicks, E. F.; Moscovitz, O.; Seeberger, P. H.; Davies, H. M. L.; Reiser, O. Visible-light mediated oxidative ring expansion of anellated cyclopropanes to fused endoperoxides with antimalarial activity. Organic Chemistry Frontiers 2020, 7, 1789–1795. doi:10.1039/d0qo00168f
  • Che, S.; Yang, Z.; Popovs, I.; Luo, H.; Luo, Y.; Guo, W.; Chen, H.; Wang, T.; Jie, K.; Wang, C.; Dai, S. A succinct strategy for construction of nanoporous ionic organic networks from a pyrylium intermediate. Chemical communications (Cambridge, England) 2019, 55, 13450–13453. doi:10.1039/c9cc06767a
  • Hloušková, Z.; Klikar, M.; Pytela, O.; Almonasy, N.; Růžička, A.; Jandová, V.; Bureš, F. Structural elaboration of dicyanopyrazine: towards push–pull molecules with tailored photoredox activity. RSC advances 2019, 9, 23797–23809. doi:10.1039/c9ra04731j
  • Chandu, P.; Ghosh, K. G.; Sureshkumar, D. Metal-Free Visible-Light-Promoted Trifluoromethylation of Vinylcyclopropanes Using Pyrylium Salt as a Photoredox Catalyst. The Journal of organic chemistry 2019, 84, 8771–8781. doi:10.1021/acs.joc.9b01033
  • Hart, J. D.; Burchill, L.; Day, A. J.; Newton, C. G.; Sumby, C. J.; Huang, D. M.; George, J. H. Visible-Light Photoredox Catalysis Enables the Biomimetic Synthesis of Nyingchinoids A, B, and D, and Rasumatranin D. Angewandte Chemie (International ed. in English) 2019, 58, 2791–2794. doi:10.1002/anie.201814089

Patents

  • BOYDSTON ANDREW J; OGAWA KELLI; GOETZ ADAM E; DUNFORD DAMIAN; MURPHY PASCUAL LAURA MARIE. Metathesis polymerization methods. US 10907010 B2, Feb 2, 2021.
  • BOYDSTON ANDREW J; OGAWA KELLI; GOETZ ADAM E; DUNFORD DAMIAN; MURPHY PASCUAL LAURA MARIE. Metathesis polymerization methods. US 10273327 B2, April 30, 2019.
Other Beilstein-Institut Open Science Activities