A Simple and Direct Method for the Palladium‐Catalyzed Oxidative Coupling of Unactivated Allylarenes with Classic Arenes

Abstract

An efficient route to engineer vinylarene structures by the PdII‐catalyzed oxidative coupling of unactivated allylarenes with classic arenes was developed. The methodology features the use of unactivated allylarenes with no prefunctionalization and classic arenes without installed directing groups. A variety of vinylarenes and their saturated derivatives were obtained.

S,O-Ligand-Promoted Palladium-Catalyzed C–H Functionalization Reactions of Nondirected Arenes

“…In addition, the C–H allylation reaction using benzene and allylbenzene as substrates was also conducted with and without L2 . 18 Again, we observed an acceleration of the reaction rate in the presence of the S,O-ligand L2 and the corresponding allylated product was obtained in 54% yield ( Scheme 3 b). In this case, no acceleration using pyridine as ligand was observed.…”

“…Moreover, the S,O-ligand showed higher activity than the pyridine ligand. In addition, the C–H allylation reaction using benzene and allylbenzene as substrates was also conducted with and without L2 . Again, we observed an acceleration of the reaction rate in the presence of the S,O-ligand L2 and the corresponding allylated product was obtained in 54% yield (Scheme b).…”

Oxidative Coupling between Two Hydrocarbons: An Update of Recent C–H Functionalizations

“…Allylarenes have also been used to couple with simple arenes by Wong and Law (Scheme 64). 109 Pd(TFA) 2 /AgOAc was the optimal catalyst/oxidant combination. The reaction was carried out in simple arene solution at 80 °C under air atmosphere.…”

Recent Developments in Palladium-Catalysed Non-Directed C–H Bond Activation in Arenes

“…Similarly, in 2014, Law and co-workers reported a catalytic system based on a highly electrophilic Pd(TFA) 2 catalyst for oxidative coupling of simple arenes with substituted allyl arenes using AgOAc as the oxidant and PivOH as the additive (Scheme 28). 56 Allyl arenes with electron-donating groups on the aromatic ring gave the desired products as mixtures of isomers in good yields. The substrate scope of simple arenes was demonstrated with alkyl, methoxy, fluoro and chloro substituents on the aromatic ring.…”