Figure 4: Three-component trifluoroethylation reactions.
From: A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid
aTypically, amine (0.50 mmol) and aldehyde (0.50 mmol) were mixed neat, before adding toluene (0.5 ml) and PhSiH3 (0.25 mmol) and stirring for 10 min at 70 °C. Trifluoroacetic acid (0.875 mmol) and further PhSiH3 (2.0 mmol) were added and the reaction heated at 70 °C for 16 h. The products were purified by concentration, washing an ether solution of the crude material with sodium bicarbonate and chromatography. Slight timing/temperature modifications are described in Supplementary Methods for: bMethod B (alkyl aldehydes), cMethod C/D (hindered aldehydes), dMethod E (ketones). e5.00 mmol scale from HCl salt of amine, ftrifluoroacetic acid (1.50 mmol) used. gtrifluoroacetic acid (1.00 mmol) used, has mixture of 93:7 trans:cis alkenes.
