Perfluoroalkylation copper-mediated

The mechanism of the copper-mediated cross-coupling of iodoarenes and perfluoroalkyl iodides is supposed to be similar to that of related reactions involving the interaction of halogenoarenes with cuprous salts of organic nucleophilic anions (for example CuCN) [55] (Scheme 2.122). First a solvated perfluoroalkyl copper(I) complex is formed. This then coordinates to the iodoarene followed by exchange of ligands [56]. Several electron-transfer steps are probably involved in this process. 

Scheme A.14 Copper-mediated perfluoroalkylation of iodoarenes by perfluoroalkyl silane reagents [20].

A. Typical Synthetic Procedures 291 A.10.2 Copper-mediated Perfluoroalkylation of Aryl Iodide 41... 

Perfluoroalkyl cooper reagent also can be generated in situ through the reaction of perfluoroalkyl anions (or their synthetic equivalents) with Cu(I) salts. First part of this section contains a brief review of major types of reagents used for copper mediated... 

Chen, G.J. Chen, L.S. Perfluoroalkylations and perfluorooxaalkylations. Part 3. Chloro-substituted diazines as substrates in copper-mediated cross-couphng. J. Fluorine Chem. 

As well as a fluorine substituent, a trifluoromethyl group have recently attracted much attention as the shortest perfluoroalkyl group. A variety of methodologies for the introduction of a trifluoromethyl group into heteroaromatics have been also developed [102], In 1970, Kobayashi et al. reported the copper-mediated direct tri-fluoromethylation of aryl and heteroaryl halides using trifluoromethyl iodide as a source of a trifluoromethyl group [103]. Thus, l-(trifluoromethyl)isoquinoline was synthesized, albeit in low yield (Scheme 29). 

---