Synthesis and structural characterization of a palladium complex as an anticancer agent, and a highly efficient and reusable catalyst for the Heck coupling reaction under ultrasound irradiation: A convenient sustainable green protocol

DOI: 10.1016/j.poly.2020.114924

Source and publish data:

Polyhedron (2021)

Update date:2022-09-26

Topics:

Authors:

El-bendary, Mohamed M.

Saleh, Tamer S.

Al-Bogami, Abdullah S.

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Article abstract of DOI:10.1016/j.poly.2020.114924

The complex [Pd(paOH)₂].2Cl (1) was synthesized by the self-assembly method with palladium chloride and pyridine-2-carbaldehyde-oxime (paOH) in aqueous acetonitrile solution under ambient conditions. Complex 1 was fully characterized by FT-IR, UV–vis and NMR spectroscopic techniques, as well as elemental analysis. The single crystal X-ray structure of complex 1 indicates that the Pd(II) ion is bonded to four nitrogen atoms from two pyridine-2-carbaldehyde-oxime ligands. The molecular geometry of the Pd(II) ion in complex 1 is distorted square-planar with a trans geometry and with two free chloride ions. Using an MTT assay, the anticancer activities of the palladium complex 1 were studied with respect to human breast cancer (MCF-7) and hepatocellular carcinoma (HePG-2) cell lines. The data obtained show that complex 1 displays strong activity towards the viability and the growth of the cancer cell lines MCF-7 and HepG2. Additionally, complex 1 exhibits excellent catalytic activity for the Heck cross-coupling reaction with water as the solvent under ultrasound irradiation. Ultrasound irradiation not only enhanced the rate and the yield of the reaction, but also promoted the in situ generation of a well-dispersed zero-valent Pd-colloidal species as the active catalyst from complex 1. Finally, the luminescence spectrum of complex 1 is discussed.

Full text of DOI:10.1016/j.poly.2020.114924

Polyhedron xxx (xxxx) xxx

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Polyhedron

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Synthesis and structural characterization of a palladium complex as an

anticancer agent, and a highly efﬁcient and reusable catalyst for the Heck

coupling reaction under ultrasound irradiation: A convenient sustainable

green protocol

a,c,

Mohamed M. El-bendary ^a,b,, Tamer S. Saleh

, Abdullah S. Al-Bogami

⇑

^aUniversity of Jeddah, College of Science, Department of Chemistry, Jeddah, Saudi Arabia

^bChemistry Department, Faculty of Science, Tanta University, 31527 Tanta, Egypt

^cGreen Chemistry Department, National Research Centre, Dokki, 12622, Giza, Egypt

a r t i c l e i n f o

a b s t r a c t

Article history:

The complex [Pd(paOH)₂].2Cl (1) was synthesized by the self-assembly method with palladium chloride

and pyridine-2-carbaldehyde-oxime (paOH) in aqueous acetonitrile solution under ambient conditions.

Complex 1 was fully characterized by FT-IR, UV–vis and NMR spectroscopic techniques, as well as ele-

mental analysis. The single crystal X-ray structure of complex 1 indicates that the Pd(II) ion is bonded

to four nitrogen atoms from two pyridine-2-carbaldehyde-oxime ligands. The molecular geometry of

the Pd(II) ion in complex 1 is distorted square-planar with a trans geometry and with two free chloride

ions. Using an MTT assay, the anticancer activities of the palladium complex 1 were studied with respect

to human breast cancer (MCF-7) and hepatocellular carcinoma (HePG-2) cell lines. The data obtained

show that complex 1 displays strong activity towards the viability and the growth of the cancer cell lines

MCF-7 and HepG2. Additionally, complex 1 exhibits excellent catalytic activity for the Heck cross-cou-

pling reaction with water as the solvent under ultrasound irradiation. Ultrasound irradiation not only

enhanced the rate and the yield of the reaction, but also promoted the in situ generation of a well-dis-

persed zero-valent Pd-colloidal species as the active catalyst from complex 1. Finally, the luminescence

spectrum of complex 1 is discussed.

Received 10 October 2020

Accepted 6 November 2020

Available online xxxx

Keywords:

Palladium

Pyridine-2-carbaldehyde-oxime

Heck cross-coupling

Anticancer agent

Luminescence

1. Introduction

times of ‘‘appearing new diseases.” Most medicinal chemists work

worldwide to introduce new organic compounds, according to a

The CAC cross-coupling reactions between aryl halide deriva-

tives and oleﬁns (the Heck reaction), catalyzed by a transition

metal catalyst (such as palladium) under mild reaction conditions

are of outstanding importance in contemporary research in organic

synthesis, in which organic synthesis nowadays focuses on sus-

tainability [1]. It is worth mentioning that the Nobel Prize in chem-

istry 2010 was awarded jointly to Akira Suzuki, Richard F. Heck and

Ei-ichi Negishi for palladium-catalyzed CAC cross couplings in

organic synthesis [2,3]. This signiﬁcantly and successfully demon-

strates the importance of developing CAC cross coupling reactions

in current modern organic chemistry. Synthetic organic chemistry

has become more important nowadays during these challenging

basic set of design rules, as novel organic compounds for biological

screening. Therefore, there is an increasing need to develop an efﬁ-

cient synthetic organic methodology for important organic reac-

tions such as ‘‘Heck CAC coupling”.

In the last decade, Dawood and Kirsching introduced a catalytic

activity study of a pyridine-2-carbaldehyde-oxime based Pd(II)-

complex covalently anchored via the oxime moiety to a glass/poly-

mer composite material for Suzuki–Miyaura cross-coupling.

Although the later catalytic activity study clariﬁed the stability

and reusability of this Pd complex, which involved the microreac-

tor technique [4], due to increasing economic and ecological pres-

sure, investigations in modern organic synthesis are now directed

to the discovery of methods that largely take into account the cri-

terion of simplicity and sustainable chemistry [5].

⇑

Corresponding authors at: University of Jeddah, College of Science, Department

of Chemistry, Jeddah, Saudi Arabia.

On the other hand, the importance of utilizing greener solvents

has permeated into all aspects of synthetic chemistry. As we know,

cross-coupling reactions are preferentially carried out in highly

E-mail addresses: mmesmaeel@uj.edu.sa, mohamed.ismail@science.tanta.edu.eg

(M.M. El-bendary), tssayed@uj.edu.sa (T.S. Saleh).

https://doi.org/10.1016/j.poly.2020.114924

Please cite this article as: M.M. El-bendary, T.S. Saleh and A.S. Al-Bogami, Synthesis and structural characterization of a palladium complex as an anticancer

agent, and a highly efﬁcient and reusable catalyst for the Heck coupling reaction under ultrasound irradiation: A convenient sustainable green protocol,

Polyhedron, https://doi.org/10.1016/j.poly.2020.114924

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Polyhedron, Corrected proof, 114924. doi:10.1016/j.poly.2020.114924

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