RSS-Feed abonnieren
DOI: 10.1055/a-2534-9086
Preparation of 3-Allenyl-4-methylenetetrahydrofurans
The National Science and Technology Council of Taiwan is thanked for financial support (NSTC112-2113-M-002-023).
Abstract
A novel method for the preparation of 3-allenyl-4-methylenetetrahydrofurans via a Pd-catalyzed enyne cyclization reaction of propargyl 2-en-4-ynyl ethers under Suzuki coupling conditions is disclosed. The reaction proceeds via Pd activation of the terminal alkyne, cyclization, formation of the allenyl moiety, and reductive elimination, leading to the final product. This methodology offers several advantages, such as easy manipulation, mild reaction conditions, and easily accessible starting materials, providing a range of trisubstituted and 1,1-disubstituted allenyl(methylene)furan derivatives.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2534-9086.
- Supporting Information
Publikationsverlauf
Eingereicht: 03. Januar 2025
Angenommen nach Revision: 06. Februar 2025
Accepted Manuscript online:
06. Februar 2025
Artikel online veröffentlicht:
17. März 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1a Muñoz MP. Chem. Soc. Rev. 2014; 43: 3164
- 1b Krause N, Winter C. Chem. Rev. 2011; 111: 1994
- 2a Hoffmann-Röder A, Krause N. Angew. Chem. Int. Ed. 2004; 43: 1196
- 2b Li Y, Bao H. Chem. Sci. 2022; 13: 8491 ; and references cited therein
- 3a Brown RW, Zamani F, Gardiner MG, Yu H, Pyne SG, Hyland CJ. T. Chem. Sci. 2019; 10: 9051
- 3b Zamani F, Pyne SG, Hyland CJ. T. J. Org. Chem. 2017; 82: 6819
- 3c Liu N, Werness JB, Guzei IA, Tang W. Tetrahedron 2011; 67: 4385
- 3d Castelhano AL, Pliura DH, Taylor GJ, Hsieh KC, Krantz A. J. Am. Chem. Soc. 1984; 106: 2734
- 3e Babudri F, Florio S, Ronzini L. Tetrahedron 1986; 42: 3905
- 5a Krause N, Purpura M. Angew. Chem. Int. Ed. 2000; 39: 4355
- 5b Ucuncu M, Karakus E, Kus M, Akpinar GE, Aksin-Artok O, Krause N, Karaca S, Elmaci N, Artok L. J. Org. Chem. 2011; 76: 5959
- 5c Chi Z, Zhou Y, Liu B, Xu X, Liu X, Liang Y. Chem. Sci. 2024; 15: 13271
- 5d Luo D, Niu S, Gong F, Xu C, Lan S, Liu J, Yang S, Fang X. ACS Catal. 2024; 14: 2746
- 6a Jiang B, Gui W.-T, Wang H.-T, Xie K, Chen Z.-C, Zhu L, Ouyang Q, Du W, Chen Y.-C. Chem. Sci. 2023; 14: 10867
- 6b Watanabe K, Nakano K, Sato H, Yamaoka T, Yoshida Y, Takita R, Kasashima Y, Sakamoto M, Mino T. J. Org. Chem. 2024; 89: 8111
- 6c Chen Z.-C, Ouyang Q, Du W, Chen Y.-C. J. Am. Chem. Soc. 2024; 146: 6422
- 7 Chiang A.-C, Liu Y.-H, Peng S.-M, Liu S.-T. Org. Lett. 2022; 24: 7649 ; and references cited therein
- 8 Grigorjeva L, Kinens A, Jirgensons A. J. Org. Chem. 2015; 80: 920
- 9 Xin X, Wang D, Wu F, Wang C, Wang H, Li X, Wan B. Org. Lett. 2013; 15: 4512
- 10 CCDC 2409623 (2a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
- 11 Pertschi R, Wagner P, Ghosh N, Gandon V, Blond G. Org. Lett. 2019; 21: 6084
- 12 Sheldrick GM. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990; 46: 467
- 13 Sheldrick GM. SHELXL-97 1997
Reviews:
Reviews: