Carbonyl fluoride iodide reaction with

As with a number of the other unsymmetrical halides, carbonyl fluoride iodide was flrst reported in the FIAT review of German science (1939-1945) [1196a,1751]. The compound was prepared by Kwasnik [1196a, 1751] from the reaction of iodine]V) fluoride with carbon monoxide according to ... 

Carbonyl or sulfonyl fluorides obtained by electrochemical fluorination yield cationic fluorinated surfactants by a reaction with MA -dimethyl-1,3-diamino-propane and quaternization with methyl iodide or dimethyl sulfate [5,160] ... 

Allyltin difluoroiodide, formed in situ by the oxidative addition of stannous fluoride to allyl iodide, is found to react with carbonyl compounds to give the corresponding homoallylic alcohols in excellent yields under mild reaction conditions (9). 

This cyclization is a reaction developed by Mori, who carried out a series of investigations with tin reagent 33. Fluoride is a much more reactive anion for initiation than any of the other halides, although it often leads to decomposition of the starting materials. In the case of vinylic or aryl halogen compounds the iodides are easier to transform than the bromides, and chlorides are unrcactive. The carbonyl group can be derived from either an aldehyde or a ketone, and even esters are sufficiently electrophilic.22... 

The thiolates, though less sensitive to basicity, are more reactive than oxygen anions over the total accessible range of basicity, but intersect the amine line at ca. pA 12. Other reactive nucleophiles which do not fall in the amine, thiolate, or oxygen anion categories are fluoride, thiosulfate, nitrite, azide, and sulfite. Halides other than fluoride, and also thiocyanate, nitrate, sulfate, and thiourea have no reactivity towards p-nitrophenyl acetate (Jencks and Carriuolo, 1960a). The total lack of reactivity of thiocyanate, iodide, bromide, and thiourea, all very polarizable nucleophiles which are reactive to sp carbon, rules out any possibility that polarizability is at all important in nucleophilic reactions at the carbonyl carbon. In general, the order of nucleophilic reactivity to p-nitrophenyl acetate correlates well with nucleophilic reactivity to other carboxylic acid derivatives (see later). Nitrite, however, shows... 

Cross-Coupling Reactions. TASF(Et) activates vinyl-, alkynyl-, and allylsilanes in the Pd-mediated cross-coupling with vinyl and aryl iodides and bromides. As illustrated in eqs 8-10, the reaction is stereospecific and chemoselective. This crosscoupling protocol is remarkably tolerant towards a variety of other functional groups such as carbonyl, amino, hydroxy, and nitro. Vinylsilanes can be synthesized from hexamethyldisilane and vinyl iodides in the presence of TASF(Et) (eq 10) via cleavage of a Si-Si bond. Aryl iodides can also be synthesized by this method. TASF is superior to tetra-n-butylanunonium fluoride for these reactions. In the absence of a vinylsilane reagent, one of the methyl groups from the difluorotrimethylsilicate is substituted for the halide (eq 11). ... 

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