60188-27-4Relevant academic research and scientific papers
Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes
Ambler, Brett R.,Peddi, Santosh,Altman, Ryan A.
supporting information, p. 2506 - 2509 (2015/05/27)
(Chemical Equation Presented) "Cu-CF3" species have been used historically for a broad spectrum of nucleophilic trifluoromethylation reactions. Although recent advancements have employed ligands to stabilize and harness the reactivity of this key organometallic intermediate, the ability of a ligand to differentiate a regiochemical outcome of a Cu-CF3-mediated or -catalyzed reaction has not been previously reported. Herein, we report the first example of a Cu-catalyzed trifluoromethylation reaction in which a ligand controls the regiochemical outcome. More specifically, we demonstrate the ability of bipyridyl-derived ligands to control the regioselectivity of the Cu-catalyzed nucleophilic trifluoromethylation reactions of propargyl electrophiles to generate (trifluoromethyl)allenes. This method provides a variety of di-, tri-, and tetrasubstituted (trifluoromethyl)allenes, which can be further modified to generate complex fluorinated substructures.
Copper-catalyzed nucleophilic trifluoromethylation of propargylic halides
Miyake, Yoshihiro,Ota, Shin-Ichi,Shibata, Masashi,Nakajima, Kazunari,Nishibayashi, Yoshiaki
supporting information, p. 7809 - 7811 (2013/09/02)
Reactions of propargylic halides with trifluoromethyltrimethylsilane in the presence of a catalytic amount of copper(i) thiophene-2-carboxylate (CuTC) have been found to give the corresponding trifluoromethylated products in good to high yields with a hig
