title: Dual catalysis with copper and rhenium for trifluoromethylation of propargylic alcohols: efficient synthesis of α-trifluoromethylated enones.
abstract: Trifluoromethylation of propargylic alcohols to provide (Z)-α-trifluoromethylated enones and β-unsubstituted α-trifluoromethylated enones proceeded with high yield and selectivity in the presence of CuI/Re2O7. The Z isomer was formed under kinetic control, though it is less stable than the E isomer in terms of steric repulsion.
authors: Synthetic Organic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan); Sodeoka Live Cell Chemistry Project, ERATO, Japan Science and Technology Agency, 2-1 Hirosawa, Wako, Saitama 351-0198 (Japan); School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526 (Japan).
authors: Hiromichi
authors: H
authors: Egami
authors: Takafumi
authors: T
authors: Ide
authors: Masashi
authors: M
authors: Fujita
authors: Toshifumi
authors: T
authors: Tojo
authors: Yoshitaka
authors: Y
authors: Hamashima
authors: Mikiko
authors: M
authors: Sodeoka
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D012211:Rhenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D007659:Ketones; D020005:Propanols; D012211:Rhenium; D003300:Copper; C028255:propargyl alcohol
keywords: copper; dual catalyst; enone; rhenium; trifluoromethyl