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A New 3,3,3-trifluoropropenylation Reagent, Ikeda–Omote Reagent
No.165(April 2015)
β-Trifluoromethylpropenylbenzene derivatives have been reported as useful compounds for liquid crystal and organic electroluminescence materials.1) (E)-Trimethyl(3,3,3-trifluoro-1-propenyl)silane (Ikeda–Omote Reagent) (1) is a new 3,3,3-trifluoropropenylation reagent, developed by Omote et al. 1 effectively participates in a Hiyama cross-coupling reaction with aryl iodide to construct β-trifluoromethylstyrene in good to excellent yields.2-4) The styrene derivative provides 2-aryl-3-trifluoromethyl-quinolines, which may make an important contribution to drug discovery.3,4) In addition, the reaction of 1 with arylaldehydes in the presence of CsF affords aryl 3,3,3-trifluoropropyl ketones5), and oxidative Sonogashira cross-coupling reaction of 1 with arylacetylenes affords 1,3-enynes with CF3 group on the terminal SP2 carbon6).
References
- 1)M. Shimizu, Y. Takeda, M. Higashi, T. Hiyama, Angew. Chem. Int. Ed. 2009, 48, 3653.
- 2)M. Omote, M. Tanaka, A. Ikeda, S. Nomura, A. Tarui, K. Sato, A. Ando, Org. Lett. 2012, 14, 2286.
- 3)M. Omote, M. Tanaka, M. Tanaka, A. Ikeda, A. Tarui, K. Sato, A. Ando, J. Org. Chem. 2013, 78, 6196.
- 4)A. Tarui, K. Sato, M. Omote, A. Ando, J. Synth. Org. Chem. Jpn. 2014, 72, 680. (Japanese)
- 5)A. Ikeda, M. Omote, S. Nomura, M. Tanaka, A. Tarui, K. Sato, A. Ando, Beilstein J. Org. Chem. 2013, 9, 2417.
- 6)A. Ikeda, M. Omote, K. Kusumoto, A. Tarui, K. Sato, A. Ando, Org. Bioml. Chem. 2015, 13, 8886.
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