I. Villuendas et al., AN EFFICIENT AND EXPEDITIOUS SYNTHESIS OF FUNCTIONALIZED TRIFLUOROMETHYL KETONES THROUGH LITHIUM-IODINE EXCHANGE-REACTION, Tetrahedron, 50(44), 1994, pp. 12673-12684
A straightforward and very efficient synthesis of unsaturated long-cha
in trifluoromethyl ketones is achieved by metallation of the correspon
ding iodides in the presence of an equimolar amount of tert-butyllithi
um, followed by reaction with a fluoroacylating agent. Metallation occ
urs quantitatively at -78 degrees C and, in contrast to what has been
generally recommended, there is no need to add the second equivalent o
f base, since its presence may be detrimental if other electrophilic f
unctions are present in the molecule.