A room temperature catalyst for toluene aliphatic C-H bond oxidation: Tripodal tridentate copper complex immobilized in mesoporous silica

Chih Cheng Liu, Tien Sung Lin, Sunney I. Chan, Chung Yuan Mou

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

A tripodal tridentate copper(II) complex, CuImph (Imph = bis(4-imidazolyl methyl)benzylamine), is synthesized to mimic the active site of copper enzymes that mediate the oxidation of aliphatic C-H bonds under mild condition. By immobilizing the model complex in the nanochannels of functionalized mesoporous silica nanoparticles (MSNs), we observe the formation of a stable bis-μ-oxo species ([{CuIIIImph}2(μ-O2-)2]2+) in the presence of dioxygen or air at ambient temperature. The dioxygen-activated CuImph@MSN samples show high reactivity and selectivity toward toluene aliphatic C-H bond oxidation, converting the toluene initially to benzyl alcohol and subsequently to benzaldehyde as the major product in a kinetic consecutive reaction. No evidence for benzoic acid is obtained, unlike the over-oxidation typically associated with present-day industrial processes operating at high temperatures. In addition, the process is self-sustaining without the requirement for a sacrificial reductant to drive the catalytic turnover. The catalyst can be fully recovered and re-used for several cycles without decay of activity.

Original languageEnglish
Pages (from-to)139-151
Number of pages13
JournalJournal of Catalysis
Volume322
DOIs
Publication statusPublished - Feb 1 2015
Externally publishedYes

Keywords

  • InChIKey OYDSZEMSAHUCCW-UHFFFAOYSA-L

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

Fingerprint

Dive into the research topics of 'A room temperature catalyst for toluene aliphatic C-H bond oxidation: Tripodal tridentate copper complex immobilized in mesoporous silica'. Together they form a unique fingerprint.

Cite this