Palladium TPPTS catalyst in water : C-allylation of phenol and guaiacol with allyl alcohol and novel isomerisation of allyl ethers of phenol and guaiacol

Abstract The use of allylic alcohols for the direct synthesis of alkenylphenols instead of allylic halides is highly attractive. However, such phenol allylations mainly lead to the production of phenyl ethers (O-allylation). We introduce herein the potential of palladium TPPTS complexes in water for a selective C-allylation of phenol and guaiacol by allyl alcohol into allylphenols and eugenols (0.8  para / ortho 2 ] + generated through the facile heterolytic cleavage of allyl alcohol or allyl phenyl ether by the Pd(0) TPPTS complex. This π-allylpalladium(II) TPPTS complex is stable in water at room temperature.