406-40-6Relevant 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
supporting information, 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.
Novel Synthesis of 2,2,2-Trifluoroethyl Compounds from Homoallylic Alcohols: A Copper(I) Iodide-initiated Trifluoromethyl-Dehydroxylation Process
Duan, Jian-Xing,Chen, Quing-Yun
, p. 725 - 730 (2007/10/02)
Benzyl, prop-2-enyl and allyl chlorodifluoroacetates 3a, bromodifluoroacetates 3b or fluorosulfonyldifluoroacetates 3c, when decomposed in the presence of 1 equivalent of copper(I) iodide at an appropriate temperature in dimethylformamide, gave the corresponding trifluoromethyl derivatives in good to excellent yields.The products can also be obtained directly by ester exchange of XCF2CO2Et (X = FSO2, Cl, Br) 6 and the corresponding alcohols in the presence of KF and CuI.A trifluoromethylation-dehydroxylation mechanism, initiated by CuI, is proposed.
Trifluoromethylation of Aliphatic Halogen Compounds
Bouillon, Jean-Philippe,Maliverney, Christian,Merenyi, Robert,Viehe, Heinz G.
, p. 2147 - 2149 (2007/10/02)
Aryl, heteroaryl or vinyl halides can be trifluoromethylated using CF3CO2Na-CuI.With alkyl iodides, however, the method fails, yielding trifluoroacetyl esters instead.Allylic halogens can be substituted with Burton's reagent, obtained from dihalogenodifluoromethane via CF3CdHal and transmetallation with CuI.A new access to trifluoropropionic acid is thereby found.Prop-2-ynyl bromide produces trifluormethylallene.Attempts at trifluoromethylation of bromoacetate with CF3CO2Na-CuI in NMP (N-methyl-2-pyrrolidone) solution led to formation of the trifluoroacetoxy derivative and of a formal adduct of hexafluoroacetone to the α position of NMP.
A facile, general route to perfluoroalkyl allenes
Burton, Donald J.,Hartgraves, Greg A.,Hsu, Jeffrey
, p. 3699 - 3702 (2007/10/02)
Perfluoroalkyl copper reagents react with propargyl halides or tosylates in DMF or DMSO at 0°C-RT to afford perfluoroalkyl allenes regiospecifically in good yield.
