Bis(trifluoromethyl)zinc•TMEDA

chemical structure image [1782974‐72‐4] C 8 H 16 F 6 N 2 Zn (MW 319.60) InChI = 1S/C6H16N2.2CF3.Zn/c1‐7(2)5‐6‐8(3)4;2*2‐1(3)4;/h5‐6H2,1‐4H3;;; InChIKey = QEVJHHUJIXGQDD‐UHFFFAOYSA‐N (trifluoromethylation reactions, difluorocyclopropanation, allylic perfluoroalkylation, remote C(sp 3 )H radical trifluoromethylation) Solubility: sol in dimethylformamide. Analysis of Reagent Purity: 1 H NMR (300 MHz, CDCl 3 ) δ 2.73 (s, 4 H ), 2.60 (s, 12 H ); 19 F NMR (282 MHz, CDCl 3 ) δ −40.5 (s, 6F). Preparative Methods: two methods have been reported for preparing Zn(CF 3 ) 2 •TMEDA ( 1 ). The first method involves a ligand exchange reaction between Zn(CF 3 ) 2 •(DMPU) 2 ( 2 ) and TMEDA. 1 Zn(CF 3 ) 2 •(DMPU) 2 ( 2 ) is prepared by mixing diethylzinc with trifluoromethyl iodide in hexanes and DMPU (2 equiv) at −20 °C for 48 h. This procedure has been applied to several other bis(fluoroalkyl)zinc reagent. The second method involves the direct synthesis of complex 1 from diethylzinc and trifluoromethyl iodide in a mixture of hexane and DMF. 2 After concentration under vacuum, DMF and TMEDA were added, and DMF was then removed to generate the title compound that was washed with diethyl ether. Purification: Zn(CF 3 ) 2 •TMEDA can be recrystallized from ether. Handling, Storage, and Precautions: the reagent is reported to be stable for at least two weeks in air but storage under argon is preferred.