One‐pot synthesis of polyfluoroterphenyls via palladium‐catalyzed Suzuki–Miyaura coupling of chlorobromobenzene and CH bond functionalization of perfluoroarenes
Abstract:An efficient tandem route for the synthesis of polyfluoroterphenyl derivatives has been developed. The target compounds were obtained in moderate to good yields by a Pd(OAc) 2 -catalyzed three-component coupling reaction involving palladium-catalyzed direct C-H activation of perfluoroarenes. This in turn will set the stage for a wide application of this useful reaction for the synthesis of fluorinated liquid crystal compounds containing the privileged polyfluoroterphenyl structure.
A simple and efficient catalytic system for Na2PdCl4 catalyzing the Suzuki‐Miyaura reaction of dibromobenzene and arylboronic acid has been developed by using 2N2O‐salen as a ligand in H2O/EtOH (V:V=4:1) at 100°C. Using this method, the reactions of substrates containing sterically demanding ortho substituents (e.g. dibromobenzene and/or arylboronic acids) proceeded efficiently, with the corresponding terphenyl derivatives being produced in moderate to excellent yields. Furthermore, this method offers interesting features for the multi‐gram scale synthesis of terphenyl compound.
Herein, we report
a one-pot process that marries mechanistically
distinct, traditional cross-coupling reactions with C–H functionalization
using the same precatalyst. The reactions proceed in yields of up
to 95%, in air, and require no extraneous ligand. The reactions are
thought to be facilitated by harnessing the substrate quinoline as
an N-ligand, and evidence of the palladium–quinoline
interaction is provided by 1H-15N HMBC NMR spectroscopy
and X-ray crystallographic structures. Application of the methodology
is demonstrated by the quick formation of fluorescent, π-extended
frameworks.
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