Visible-light-induced bromoetherification of alkenols for the synthesis of β-bromotetrahydrofurans and -tetrahydropyrans

Run Lin, Hongnan Sun, Chao Yang, Youdong Yang, Xinxin Zhao and Wujiong Xia
Beilstein J. Org. Chem. 2015, 11, 31–36. https://doi.org/10.3762/bjoc.11.5

Supporting Information

Supporting Information File 1: 1H and 13C NMR spectra for products.
Format: PDF Size: 2.7 MB Download

Cite the Following Article

Visible-light-induced bromoetherification of alkenols for the synthesis of β-bromotetrahydrofurans and -tetrahydropyrans
Run Lin, Hongnan Sun, Chao Yang, Youdong Yang, Xinxin Zhao and Wujiong Xia
Beilstein J. Org. Chem. 2015, 11, 31–36. https://doi.org/10.3762/bjoc.11.5

How to Cite

Lin, R.; Sun, H.; Yang, C.; Yang, Y.; Zhao, X.; Xia, W. Beilstein J. Org. Chem. 2015, 11, 31–36. doi:10.3762/bjoc.11.5

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

  • Banoun, C.; Bourdreux, F.; Magnier, E.; Dagousset, G. Site-Selective γ-Trihalomethylation and γ-Dihalomethylidenation of Silyl Dienol Ethers under Organophotoredox Catalysis. Chemistry (Weinheim an der Bergstrasse, Germany) 2024, e202403598. doi:10.1002/chem.202403598
  • Zhang, Z.; Li, Y.; Wang, Y.; Hua, X.; Zheng, C.; Shi, Q.; Tan, Z.; Zheng, L.; Guo, W. Photocatalytic One-Pot Three-Component Reaction for the Regioselective Synthesis of Bromo-Substituted Pyrazoles. The Journal of organic chemistry 2024, 89, 16809–16827. doi:10.1021/acs.joc.4c02122
  • Anosike, I. S.; Beng, T. K. Harnessing the 1,3-azadiene-anhydride reaction for the regioselective and stereocontrolled synthesis of lactam-fused bromotetrahydropyrans by bromoetherification of lactam-tethered trisubstituted tertiary alkenols. RSC advances 2024, 14, 18501–18507. doi:10.1039/d4ra02523g
  • Wu, Z.-W.; Kong, H.-H.; Wei, Y.; Zhou, W.-C.; Wang, L.; Lu, L.-Q.; Yang, Q.-Q. Photoinduced radical cascade brominative addition/spirocyclization of N-arylpropiolamides and CBr4 with O2 as oxidant. Green Synthesis and Catalysis 2024. doi:10.1016/j.gresc.2024.01.004
  • Tu, M.; Chen, B.-J.; Rukhsana; Cui, W.; Fu, W.; Shen, C.; Shen, Y.-M. Visible light-triggered synthesis of oxime ethers using tetrabromomethane as a mediator. New Journal of Chemistry 2022, 46, 23276–23281. doi:10.1039/d2nj04615f
  • Wang, F.; Pan, S.; Zhu, S.; Chu, L. Selective Three-Component Reductive Alkylalkenylation of Unbiased Alkenes via Carbonyl-Directed Nickel Catalysis. ACS Catalysis 2022, 12, 9779–9789. doi:10.1021/acscatal.2c02163
  • Kumar, S.; Shah, T.; Punniyamurthy, T. Recent advances in the application of tetrabromomethane in organic synthesis. Organic Chemistry Frontiers 2021, 8, 4288–4314. doi:10.1039/d0qo01369b
  • Talukdar, R. Tracking down the brominated single electron oxidants in recent organic red-ox transformations: photolysis and photocatalysis. Organic & biomolecular chemistry 2020, 18, 8294–8345. doi:10.1039/d0ob01652g
  • Lu, X.-Y.; Li, J.-S.; Wang, J.-Y.; Wang, S.-Q.; Li, Y.-M.; Zhu, Y.-J.; Zhou, R.; Ma, W.-J. Cu-catalyzed cross-coupling reactions of vinyl epoxide with organoboron compounds: access to homoallylic alcohols. RSC advances 2018, 8, 41561–41565. doi:10.1039/c8ra09048c
  • Crespi, S.; Fagnoni, M. Photocatalyzed Formation of Heterocycles. Topics in Heterocyclic Chemistry; Springer International Publishing, 2018; Vol. 54, pp 1–69. doi:10.1007/7081_2017_13
  • Tripathi, S.; Yadav, L. D. S. Visible-light-enabled denitrative carboxylation of β-nitrostyrenes: a direct photocatalytic approach to cinnamic acids. New Journal of Chemistry 2018, 42, 3765–3769. doi:10.1039/c7nj04578f
  • Rackl, D.; Kais, V.; Lutsker, E.; Reiser, a. O. Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation. European journal of organic chemistry 2017, 2017, 2130–2138. doi:10.1002/ejoc.201700014
  • Lin, R.; Sun, H.; Yang, C.; Xia, W. Visible-Light-Induced Intramolecular Chloroetherfication of Electron-Enriched Styrenes. Asian Journal of Organic Chemistry 2016, 6, 418–421. doi:10.1002/ajoc.201600441
  • Moriyama, K.; Nishinohara, C.; Togo, H. Magnesium Lewis Acid Assisted Oxidative Bromoetherification Involving Bromine Transfer from Alkyl Bromides with Aldehydes by Umpolung of Bromide. Chemistry (Weinheim an der Bergstrasse, Germany) 2016, 22, 11934–11939. doi:10.1002/chem.201602055
  • Feng, L.; Yan, H.; Yang, C.; Chen, D.; Xia, W. Visible-Light Induced Direct Synthesis of Polysubstituted Furans from Cyclopropyl Ketones. The Journal of organic chemistry 2016, 81, 7008–7022. doi:10.1021/acs.joc.6b00436
  • Wang, Y.; Jiang, M.; Liu, J.-T. Copper‐Catalyzed Diastereoselective Synthesis of Trifluoromethylated Tetrahydrofurans. Advanced Synthesis & Catalysis 2016, 358, 1322–1327. doi:10.1002/adsc.201501166
  • Yang, Q.-Q.; Marchini, M.; Xiao, W.-J.; Ceroni, P.; Bandini, M. Visible-Light-Induced Direct Photocatalytic Carboxylation of Indoles with CBr4 /MeOH. Chemistry (Weinheim an der Bergstrasse, Germany) 2015, 21, 18052–18056. doi:10.1002/chem.201503787
  • Angnes, R. A.; Li, Z.; Correia, C. R. D.; Hammond, G. B. Recent synthetic additions to the visible light photoredox catalysis toolbox. Organic & biomolecular chemistry 2015, 13, 9152–9167. doi:10.1039/c5ob01349f
  • Lin, R.; Sun, H.; Yang, C.; Yang, Y.; Zhao, X.; Xia, W. Visible-Light-Induced Bromoetherification of Alkenols for the Synthesis of β-Bromotetrahydrofurans and -tetrahydropyrans. ChemInform 2015, 46. doi:10.1002/chin.201520044
Other Beilstein-Institut Open Science Activities