Pd nanoparticles immobilized on magnetic chitosan as a
novel reusable catalyst for green Heck and Suzuki
cross‐coupling reaction: In water at room temperature
Abdol R. Hajipour
| Ali R. Sadeghi
| Zahra Khorsandi
Department of Chemistry, Isfahan
University of Technology, Isfahan 84156,
Department of Pharmacology, University
of Wisconsin, Medical School, 1300
University Avenue, Madison 53706‐1532,
Abdol R. Hajipour, Department of
Chemistry, Isfahan University of
Technology, Isfahan 84156, IR Iran.
Isfahan University of Technology (IUT);
Center of Excellence in Sensor and Green
Chemistry Research (IUT)
A novel type of magnetically responsive chitosan nanocomposite was success-
fully synthesized as a green and high powerful palladium‐based heterogeneous
catalyst and its efficiency in Heck and Suzuki cross‐coupling was evaluated.
This catalyst promote a large library of functional substrates of these reactions
under mild and sustainable conditions (water or ethanol as solvent, at room
temperature, in significantly short reaction time (20 minutes)) and stand as
recyclable, metal scavenging catalytic systems.
heck and Suzuki reaction, magnetic chitosan, room temperature conditions, water
1 | INTRODUCTION
One of the most ideal strategies is to perform coupling
reactions in low‐cost, safe and environmentally friendly
conditions, such as ambient temperature and water as
the only solvent.
The use of this solvent alone has fun-
damental merit in that water is inexpensive, nontoxic, and
safe. Existing approaches in water without any co‐solvents
require considerable heating
and there are few exam-
ples of transition‐metal‐based cross‐coupling reactions
which run in pure water at room temperature involving
water‐insoluble substrates. Herein, we describe the use of
novel catalytic system that allow, for the first time, Heck
and Suzuki cross‐couplings to be run at room temperature
and in green solvent.
Palladium‐catalyzed Heck cross‐coupling reactions is
known as one of the most common and practical method
for the construction of new carbon–carbon bonds
which have widely applications for the synthesis of a large
variety of organic substances, bioactive compounds and
Numerous heterogenization methods applying various
solid supports such as charcoal, inorganic silica, alumina
and synthetic polymers have been developed.
reported heterogeneous catalysts have higher reusability
but stability and environmental properties is their most
important weakness. For example, carbon nanotubes as
one of the most interested solid support have been found
as a serious health hazard materials.
In addition to,
mesoporous silica is instable in aqueous and basic
One of the excellent candidate as a support for cata-
lysts is chitosan, it is produced from a key constituent of
the exoskeletons of crustaceans.
Chitosan has been
exhibited biopesticidal, antifungal and anticancer proper-
ties and can be used as absorbents for metals in medicine
and drug delivery.
Functionalization of chitosan with various ligands can
provide coordination sites that make it sufficient for metal
Therefore, several catalytic systems using
chitosan as a support are reported and their applications
in some reaction such as oxidation, cyclopropanation of
Received: 8 July 2017 Revised: 17 August 2017 Accepted: 17 August 2017
Appl Organometal Chem. 2018;32:e4112.
Copyright © 2017 John Wiley & Sons, Ltd.wileyonlinelibrary.com/journal/aoc 1of11