Reactions of Pentafluorophenyltrimethylsilane with Bis (2, 2'-bipyridine)copper(II) Fluoride

Abstract

Reactions of pentafluorophenyltrimethylsilane [1] with bis(2, 2'-bipyridine)copper(II)fluoride [2] were examined under various conditions. (Table 1) The reactions gave pentafluorobenzene [3] along with decafluorobiphenyl[4]
The addition of benzaldehyde into the reaction mixture did not differ the results, giving no adduct of benzaldehyde. The addition of iodobenzene and copper powder yielded pentafluorobiphenyl [5] in addition to [3] while no [4] was produced at all. Without copper powder the reaction afforded the mixture of [3], [4], Cali and [5]. The choice of solvents affected the selectivity of products. These products were conceivably produced under mild conditions via pentafluorophenylcopper(II) [6] and -(I) [8] as illustrated in Scheme 1.