Triazine functionalized ordered mesoporous polymer: a novel solid support for Pd-mediated C–C cross-coupling reactions in water

Abstract

A new functionalized mesoporous polymer (MPTAT-1) has been synthesized via organic–organic radical polymerization of 2,4,6-triallyloxy-1,3,5-triazine (TAT) in aqueous medium in the presence of an anionic surfactant (sodium dodecyl sulfate) as template. Powder XRD and TEM image analysis suggests the presence of ordered 2D-hexagonal arrangement of pores in the material. N₂ sorption analysis reveals a moderately good surface area 135 m² g⁻¹ for this mesoporous polymer. The template free MPTAT-1 acts as an excellent support for immobilizing Pd(II) at its surface and the resulting material showed very good catalytic activity in several C–C cross-coupling reactions like Mizoroki–Heck, Sonogashira and Suzuki–Miyaura in an environmentally benign reaction medium, water. The catalyst exhibits very high catalytic activity for the coupling of various aryl halides including aryl chlorides with alkenes or alkynes and the sodium salt of (trihydroxy)phenylborate. Due to strong binding with the functional groups of the polymer, the anchored Pd(II) could not leach out from the surface of the mesoporous catalyst during the reaction and it has been reused several times without appreciable loss in catalytic activity.