POLYFLUOROALKYLATION OF BROMOHETEROCYCLIC COMPOUNDS VIA PERFLUOROALKYLCOPPER INTERMEDIATES

Article abstract of DOI:10.1016/S0022-1139(00)81565-1

Reactions between n-C6F13I, Cu and various bromoheterocyclic compounds in dimethyl sulfoxide provide a convenient method for the perfluoroalkylation of heterocyclic compounds.By this method perfluoroalkylated products of pyridine and pyrimidine were synthesized in near quantitative yields.Perfluoroalkylation of bromofurans and bromothiophenes also provided good yields of perfluoroalkylated products, however, competing reactions also yielded various by-products indicative of reductive dehalogenation, homocoupling, polysubstitution beyond the number of C-Br bonds in the starting heterocyclic compound and formation of structural isomers.