1628200-45-2Relevant academic research and scientific papers
Synthesis of Trifluoromethyl-allenes by Gold-Catalyzed Rearrangement of Propargyl Benzyl Ethers
Boreux, Arnaud,Lonca, Geoffroy H.,Riant, Olivier,Gagosz, Fabien
, p. 5162 - 5165 (2016/10/14)
A new method for the synthesis of trifluoromethyl-allenes from easily accessible α-trifluoromethyl-propargyl benzyl ether derivatives following a gold-catalyzed intramolecular hydride transfer has been developed. Various di- and trisubstituted trifluoromethyl-allenes were obtained in good to excellent yields.
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 decarboxylative trifluoromethylation of propargyl bromodifluoroacetates
Ambler, Brett R.,Peddi, Santosh,Altman, Ryan A.
, p. 1938 - 1946 (2014/07/22)
The development of efficient methods for accessing fluoA rinated functional groups is desirable. Herein, we report a two step method that utilizes catalytic copper for the decarboxylative trifluoromethylation of propargyl bromodifluoroacetates is described. This protocol affords a mixture of propargyl trifluoromethanes and trifluoromethyl allenes. Georg Thieme Verlag Stuttgart New York.
