by Glutaraldehyde as an Efficient Catalyst
for the Mizoroki
Heck Reaction1
Z. Wang, M. Xu, L. Shao, and C. Qi*
Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process,Shaoxing University,
Zhejiang Province 312000, P.R. China
*e-mail: qichenze@usx.edu.cn
Received June 17, 2015
Abstract—Nonwoven chitosan (CS) nanofiber mats were successfully prepared by the electrospinning of the mix-
ture of CS and poly(ethylene oxide) (PEO) in acetic acid aqueous solution. The CS/PEO fiber mats were treated
with glutaraldehyde aqueous solution to stabilize fibers in solution. The concentration of glutaraldehyde is impor-
tant for incorporating swelling properties in the cross-linked CS/PEO fiber mats. The cross-linked CS/PEO fibers
(CCS/PEO fibers) were then used as supports for palladium catalysts in the Mizoroki–Heck reaction. The results
of the study demonstrated that the catalytic activities of Pd catalyst supported on CCS/PEO fiber (Pd-CCS/PEO
fiber) were highly dependent on the concentration of glutaraldehyde in the cross-linking process. Density func-
tional theory (DFT) calculations indicated that the Schiff bond formed between CS and glutaraldehyde could
reduce the energy needed to form a chelate complex between the CCS/PEO fibers and palladium active species.
This in turn could decrease the activation energy of the Mizoroki–Heck reactions which occur in the presence of
the Pd-CCS/PEO fiber catalysts. The optimized Pd-CCS/PEO fiber catalyst was very efficient and stable in the
Mizoroki–Heck reaction of aromatic iodides with olefins.
Keywords: chitosan, electrospinning, palladium, DFT calculation, Mizoroki–Heck reaction
DOI: 10.1134/S0023158416030149
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