NHC Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling Reactions of Aryl Boronate Esters with Perfluorobenzenes

An efficient Suzuki–Miyaura
cross-coupling reaction of perfluorinated
arenes with aryl boronate esters using NHC nickel complexes as catalysts
is described. The efficiencies of different boronate esters (p-tolyl-Beg, p-tolyl-Bneop, p-tolyl-Bpin, p-tolyl-Bcat) and the corresponding
boronic acid (p-tolyl-B­(OH)2) in this
type of cross-coupling reaction were evaluated (eg, ethyleneglycolato;
neop, neopentylglycolato; pin, pinacolato; cat, catecholato). Aryl-Beg
was shown to be the most reactive boronate ester among those studied.
The use of CsF as an additive is essential for an efficient reaction
of hexafluorobenzene with aryl neopentylglycolboronates.