PERFLUOROALKYLATIONS AND PERFLUOROOXAALKYLATIONS .1. BROMOAROMATICS AS SUBSTRATES IN COPPER-MEDIATED CROSS-COUPLING

Tribromobenzenes, bromobiphenyl ethers and a bromoterphenyl ether have been used as substrates in copper-mediated cross-coupling reactions w ith perfluoroalkyl and per fluorooxaalkyl iodides. Excellent yields we re obtained from perfluoroalkyl iodides as well as the ether iodides i n 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 react ivity is based on the relative position of the ether linkage to the re action site and was more pronounced in reactions with aryl bromides th an in reactions with aryl iodides.