A highly efficient catalyst for Suzuki–Miyaura coupling reaction of benzyl chloride under mild conditions

Abstract

Diarylmethane derivatives, essential building blocks in organic synthesis, are usually synthesized through the traditional electrophilic substitution reaction i.e., Friedel–Crafts reaction, which suffers from the rearrangement and weak reactivity of aromatic compounds with deactivating/electron-withdrawing groups. The Suzuki–Miyaura coupling reaction of low-cost benzyl chloride as an alternative method overcomes these defects. Pd(II) organometallic catalysts immobilized on the triphenylphosphine-functionalized microporous knitting aryl polymer (KAPs(Ph-PPh₃)-Pd) as a novel heterogeneous catalyst was employed in Suzuki–Miyaura coupling reaction of benzyl chloride and exhibited excellent catalytic activity under mild conditions with a turnover frequency (TOF) up to 76 min⁻¹ (4569 h⁻¹). This work reveals that the microporous structure of the catalyst can rapidly adsorb substrates, consequently facilitating their interaction, and eventually promoting the catalytic efficiency.