Perfluoroalkylations and perfluorooxaalkylations. Part 1. Bromoaromatics as substrates in copper-mediated cross-coupling

Abstract Tribromobenzenes, bromobiphenyl ethers and a bromoterphenyl ether have been used as substrates in copper-mediated cross-coupling reactions with perfluoroalkyl and perfluorooxaalkyl iodides. Excellent yields were obtained from perfluoroalkyl iodides as well as the ether iodides in which the ether oxygen was situated at position 5 or higher. However, ether iodides where the ether oxygen was at the 3-position gave only traces of the cross-coupled product, if any. This difference in reactivity is based on the relative position of the ether linkage to the reaction site and was more pronounced in reactions with aryl bromides than in reactions with aryl iodides.