Application of the Fluorous-Biphase Concept to Palladium-Catalyzed Sonogashira Couplings

Abstract

Sonogashira C,C couplings in a fluorous biphasic system by application of three differently perfluoro-tagged Pd complexes are reported. All three complexes were probed in the coupling of four bromoarenes to three alkynes. The parallel workup procedure allowed for straightforward product isolation and catalyst recovery by simple extraction steps. In particular, the coupling of electron-deficient bromoarenes proceeded with good yields and allowed for the catalyst to be used up to three times.