A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamates

Olusesan K. Koleoso, Matthew Turner, Felix Plasser and Marc C. Kimber
Beilstein J. Org. Chem. 2020, 16, 1983–1990. https://doi.org/10.3762/bjoc.16.165

Supporting Information

Supporting Information File 1: Experimental details, analytical (1H NMR, 13C NMR) and ESIMS data.
Format: PDF Size: 3.8 MB Download

Cite the Following Article

A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamates
Olusesan K. Koleoso, Matthew Turner, Felix Plasser and Marc C. Kimber
Beilstein J. Org. Chem. 2020, 16, 1983–1990. https://doi.org/10.3762/bjoc.16.165

How to Cite

Koleoso, O. K.; Turner, M.; Plasser, F.; Kimber, M. C. Beilstein J. Org. Chem. 2020, 16, 1983–1990. doi:10.3762/bjoc.16.165

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.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 157.2 KB Download

Citations to This Article

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

Scholarly Works

  • Quintavalla, A.; Carboni, D.; Brusa, A.; Lombardo, M. Selective Hydrofunctionalization of N-Allenyl Derivatives with Heteronucleophiles Catalyzed by Brønsted Acids. The Journal of organic chemistry 2024, 89, 2320–2342. doi:10.1021/acs.joc.3c02322
  • Zhang, J.; Liang, W.; Yang, Y.; Yan, F.; Liu, H. Regiocontrollable Difunctionalization of N-Allenamines. Chinese Journal of Organic Chemistry 2024, 44, 335. doi:10.6023/cjoc202309006
  • Cheng, S.; Gu, W.; Zhao, K.; Zhang, S. T.; Yang, L.; Liu, Q. S.; Li, X. X.; Zhao, Z. G. NIS-mediated regioselective addition of allenamides with pyrazoles: synthesis of iodo-substituted allylic pyrazoles. New Journal of Chemistry 2023, 47, 19698–19708. doi:10.1039/d3nj03326k
  • Zhao, K.; Liu, Q.; Cheng, S.; Zhao, Z.; Li, X. PhI(OAc)2-Mediated Regioselective Hydrothiolation of Allenamides with Thiophenol via a Radical Process: Synthesis of Vinyl Sulfides. The Journal of organic chemistry 2023, 88, 15626–15638. doi:10.1021/acs.joc.3c01605
  • Hourtoule, M.; Miesch, L. Construction of C-N and C-O bonds based on N-allenamide functionalization. Organic & biomolecular chemistry 2022, 20, 9069–9084. doi:10.1039/d2ob01768g
  • Tan, X.; Zhao, K.; Zhong, X.; Yang, L.; Dong, Y.; Wang, T.; Yu, S.; Li, X.; Zhao, Z. Synthesis of 1,2-diselenides via potassium persulfate-mediated diselenation of allenamides with diselenides. Organic & biomolecular chemistry 2022, 20, 6566–6570. doi:10.1039/d2ob00964a
  • Huang, M.; Deng, L.; Lao, T.; Zhang, Z.; Su, Z.; Yu, Y.; Cao, H. Mechanochemically Induced Dehydrogenation Coupling and [3+2] Cycloaddition of Indolizines with Allenes Using Piezoelectric Materials. The Journal of organic chemistry 2022, 87, 3265–3275. doi:10.1021/acs.joc.1c02940
  • Quintavalla, A.; Veronesi, R.; Speziali, L.; Martinelli, A.; Zaccheroni, N.; Mummolo, L.; Lombardo, M. Allenamides Playing Domino: A Redox-Neutral Photocatalytic Synthesis of Functionalized 2-Aminofurans. Advanced Synthesis & Catalysis 2021, 364, 362–371. doi:10.1002/adsc.202101015
  • Singh, J.; Sharma, A.; Sharma, A. Visible light mediated functionalization of allenes. Organic Chemistry Frontiers 2021, 8, 5651–5667. doi:10.1039/d1qo00955a
  • Pradhan, T. R.; Paudel, M.; Harper, J. L.; Cheong, P. H.-Y.; Park, J. K. Characterization and Utilization of the Elusive α,β-Unsaturated N-Tosyliminium: the Synthesis of Highly Functionalizable Skipped Halo Enynes. Organic letters 2021, 23, 1427–1433. doi:10.1021/acs.orglett.1c00103
Other Beilstein-Institut Open Science Activities