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

作者:Guan Zhenhong; Li Buyi; Hai Guoliang; Yang Xinjia; Li Tao*; Tan Bien
来源:RSC Advances, 2014, 4(69): 36437-36443.
DOI:10.1039/c4ra06551d

摘要

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.