Tnfluoromethyl iodide

Examples of perfluoroalkyl iodide addition to the triple bond include free radical addition of perfluoropropyl iodide to 1 -heptyne [28] (equation 21), thermal and free radical-initiated addition of lodoperfluoroalkanesulfonyl fluorides to acetylene [29] (equation 22), thermal addition of perfluoropropyl iodide to hexa-fluoro 2 butyne [30] (equation 23), and palladium-catalyzed addition of per-fluorobutyl iodide to phenylacetylene [31] (equation 24) The E isomers predominate in these reactions Photochemical addition of tnfluoromethyl iodide to vinylacetylene gives predominantly the 1 4 adduct by addition to the double bond [32] Platinum catalyzed addition of perfluorooctyl iodide to l-hexyne in the presence of potassium carbonate, carbon monoxide, and ethanol gives ethyl () per fluorooctyl-a-butylpropenoate [JJ] (equation 25)... 

BURTON Trilluoromelhylation Tnfluoromethylation of aryl iodides with Cd (Cu) reagents... 

The first perfluoroalkykadmium compounds were prepared via metathesis between bis(trifluaromethyl)mercury and dialkylcadmiums [12d] An equilibrium mixture of all possible cadmium and mercury compounds was formed, the equilibrium could be shifted toward the bis(tnfluoromethyl)cadmium by using excess bis(tnflu-oromethyl)mercury When the reaction was earned out in glyme, a stable bis(tnflu-oromethyl)cadmium gly ine complex was isolated [124, 125 126] (equation 96) Other analogues were synthesized and isolated in essentially quantitative yield via direct reaction of primary and secondary perfluoroalkyl iodides with di-alkylcadmiums in basic Lewis solvents [127 128] (equaUon 97)... 

Cheaper sources of tnfluoromethyl groups have been the goal of several groups The use of sodium trifluoroacetate and copper (I) iodide in dipolar aprotic solvents gave regiospecific trifluoromethylation of aromatic halides [202] (equation 136)... 

Tnfluoromethylation of aryl iodides was carried out by the fluoride ion in duced cross-coupling reaction of aromatic iodides with trifluoromethyltnalkyl-silanes in the presence of copper salts [219] (equation 147) Some pentafluoro- ethyl derivative was also formed This methodology was extended to pentafluoroethyl-and heptafluoropropyltriethylsilanes [219]... 

---