Vol:.(1234567890)
Catal Lett (2017) 147:2640–2655
DOI 10.1007/s10562-017-2170-x
1 3
Thiophene Methanimine–Palladium Schiff Base Complex
Anchored on Magnetic Nanoparticles: A Novel, Highly Efficient
and Recoverable Nanocatalyst for Cross-Coupling Reactions
in Mild and Aqueous Media
γ-Fe
2
O
3
/AEPH
2
-TC-Pd Catalyzed Suzuki–Miyaura and Heck–Mizoroki Reactions
Roya Jahanshahi
1
· Batool Akhlaghinia
1
Received: 8 June 2017 / Accepted: 14 August 2017 / Published online: 28 August 2017
© Springer Science+Business Media, LLC 2017
Graphical Abstract
Keywords γ-Fe
2
O
3
/AEPH
2
-TC-Pd · Sustainable
chemistry · Magnetically separable nanocatalyst ·
Palladium–Schiff base complex · Suzuki–Miyaura · Heck–
Mizoroki
1 Introduction
Nowadays, novel approaches focus on development of more
environmentally sustainable chemical processes in both aca-
demic and industrial viewpoints [1]. One of the important
criteria that support a chemical transformation in a move-
ment toward the green chemistry, is utilizing the heterogene-
ous catalytic systems instead of their homogeneous coun-
terparts [2, 3]. Although homogeneous catalysts provide
excellent activity and selectivity, they are encounter with the
problems associated with catalyst separation, catalyst recy-
cling and the contamination of the ligand or metal residue
in the final products [4]. On the other hand, in spite of hav-
ing substantial merits in terms of stability and reusability,
heterogeneous catalysts have lower activity and selectivity
Abstract In this study, a novel thiophene methanimine–
palladium Schiff base complex anchored on decorated
γ-Fe
2
O
3
with 2-aminoethyl dihydrogen phosphate (γ-Fe
2
O
3
/
AEPH
2
-TC-Pd) was synthesized as a new magnetically sep-
arable nanocatalyst. Characterization of the new designed
nanocatalyst was performed successfully using different
techniques such as FT-IR, XRD, XPS, TEM, TGA, VSM,
ICP and elemental analysis. This nanocatalyst presented a
superb catalytic activity for Suzuki–Miyaura and Heck–Miz-
oroki cross-coupling reactions. The most important features
of the prepared catalytic system which makes the current
protocol more beneficial from both industrial and environ-
mental viewpoints are its ease of recovery and reusability
up to nine cycles without appreciable loss of the catalytic
performance, as well as accomplishing the reactions under
mild conditions in aqueous media which is a great challenge
in some cross-coupling reactions.
Electronic supplementary material The online version of this
article (doi:10.1007/s10562-017-2170-x) contains supplementary
material, which is available to authorized users.
* Batool Akhlaghinia
akhlaghinia@um.ac.ir
1
Department of Chemistry, Faculty of Sciences, Ferdowsi
University of Mashhad, Mashhad 9177948974, Iran