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n-Butyllithium-promoted regioselective elimination of vicinal bis-triflate having an adjacent ether oxygen |
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| Authors: | Noriki Kutsumura Kota Shibuya Hitoshi Yamaguchi Takao Saito |
| Affiliation: | 1. International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8575, Japan;2. Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan |
| Abstract: | Regioselective elimination of a vicinal bis-triflate having an adjacent ether oxygen functional group has been developed. Considered in the context of our studies of the regioselective elimination of vicinal dibromide, the key to the mechanism involves the electron-withdrawing inductive effect of the neighboring oxygen functional group. Aliphatic vinyl triflate was shown to be effective in Suzuki–Miyaura cross coupling compared with corresponding aliphatic vinyl bromide. |
| Keywords: | Vinyl triflate Regioselective elimination Vicinal bis-triflate Electron-withdrawing inductive effect Neighboring-group effect |
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