Polymer supported palladium complex as a reusable catalyst for Suzuki coupling

Article abstract of DOI:10.1016/j.jorganchem.2018.08.012

Novel, simple and efficient catalytic system based on a polymer supported Pd complex of 2,6-bis(benzimidazolyl)pyridine, Pd(PS–BBP)Cl₂, was found to be highly active for Suzuki–Miyaura cross-coupling of aryl halides with phenylboronic acids under mild conditions. The catalyst was characterized by CHN analyses, thermogravimetric analyses, BET surface area measurements, ICP-OES, FT-IR and electronic spectral studies. The effect of solvent, base, temperature and catalyst concentration on the coupling reaction of iodobenzene with phenylboronic acid was also investigated. A variety of functional groups are tolerated. The novel catalyst could be recovered in a facile manner from the reaction mixture and could be reused up to seven times without significant loss of catalytic activity.

Full text of DOI:10.1016/j.jorganchem.2018.08.012

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Accepted Manuscript
Polymer supported palladium complex as a reusable catalyst for Suzuki coupling
M.K. Renuka, V. Gayathri
PII:
S0022-328X(18)30454-6
10.1016/j.jorganchem.2018.08.012
JOM 20539
DOI:
Reference:
To appear in: Journal of Organometallic Chemistry
Received Date: 22 May 2018
Revised Date: 1 August 2018
Accepted Date: 14 August 2018
Please cite this article as: M.K. Renuka, V. Gayathri, Polymer supported palladium complex as a
reusable catalyst for Suzuki coupling, Journal of Organometallic Chemistry (2018), doi: 10.1016/
j.jorganchem.2018.08.012.
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ACCEPTED MANUSCRIPT
Polymer supported palladium complex as a reusable catalyst for Suzuki coupling
Renuka M K and Gayathri V*
Department of Post Graduate Studies in Chemistry, Central College City Campus, Bangalore
University, Dr. Ambedkar Street, Bangalore 560001, Karnataka, India.
*Corresponding author e-mail: gayathritvr@yahoo.co.in, Phone: 080-22961348
Abstract
Novel, simple and efficient catalytic system based on a polymer supported Pd complex of 2,6-
bis(benzimidazolyl)pyridine, Pd(PS-BBP)Cl2, was found to be highly active for Suzuki–
Miyaura cross-coupling of aryl halides with phenylboronic acids under mild conditions. The
catalyst was characterized by CHN analyses, thermogravimetric analyses, BET surface area
measurements, ICP-OES, FT-IR and electronic spectral studies. The effect of solvent, base,
temperature and catalyst concentration on the coupling reaction of iodobenzene with
phenylboronic acid was also investigated. A variety of functional groups are tolerated. The novel
catalyst could be recovered in a facile manner from the reaction mixture and could be reused up
to seven times without significant loss of catalytic activity.

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.
ACCEPTED MANUSCRIPT
Polymer supported palladium complex as a reusable catalyst for Suzuki coupling
Renuka M K and Gayathri V*
Department of Post Graduate Studies in Chemistry, Central College City Campus, Bangalore
University, Dr. Ambedkar Street, Bangalore 560001, Karnataka, India.
*Corresponding author e-mail: gayathritvr@yahoo.co.in, Phone: 080-22961348
Graphical Abstract

Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.
ACCEPTED MANUSCRIPT
Polymer supported palladium complex as a reusable catalyst for Suzuki coupling
Renuka M K and Gayathri V*
Department of Post Graduate Studies in Chemistry, Central College City Campus, Bangalore
University, Dr. Ambedkar Street, Bangalore 560001, Karnataka, India.
*Corresponding author e-mail: gayathritvr@yahoo.co.in, Phone: 080-22961348
Abstract
Novel, simple and efficient catalytic system based on a polymer supported Pd complex of 2,6-
bis(benzimidazolyl)pyridine, Pd(PS-BBP)Cl2, was found to be highly active for Suzuki–
Miyaura cross-coupling of aryl halides with phenylboronic acids under mild conditions. The
catalyst was characterized by CHN analyses, thermogravimetric analyses, BET surface area
measurements, ICP-OES, FT-IR and electronic spectral studies. The effect of solvent, base,
temperature and catalyst concentration on the coupling reaction of iodobenzene with
phenylboronic acid was also investigated. A variety of functional groups are tolerated. The novel
catalyst could be recovered in a facile manner from the reaction mixture and could be reused up
to seven times without significant loss of catalytic activity.
Keywords Aryl halides; phenylboronic acids; biphenyls; cross-coupling; palladium(II) complex
1. Introduction
The Pd–catalyzed Suzuki–Miyaura coupling (SMC) reaction is a highly useful and versatile
method for the construction of carbon-carbon bonds [1]. The reaction is particularly important to
afford unsymmetrical biaryl compounds, which are frequently encountered as core structural
motifs in pharmaceuticals, agrochemicals and organic materials [2–4]. Conventionally, these
cross-coupling reactions employ halogen-containing aromatic compounds such as aryl halides as
electrophilic coupling partners, while aromatic boron compounds serve as nucleophilic coupling
partners.
These cross-coupling reactions are generally catalyzed with soluble palladium complexes in an
organic solvent or in a mixture of water and an organic solvent [5–8]. However, there has been a
continuing challenge with such catalyst systems regarding their efficient separation and
recycling, these are important considerations for economic and ecological reasons.
Heterogeneous palladium-catalyst systems have been found to be highly effective for
overcoming some of these problems [9–13]. Heterogeneous catalysts generally comprise an
organic or inorganic solid support, a linkage moiety, and a catalytic center prepared from a
transition metal salt and ligand. Amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin-
supported terpyridine-metal complex is an active catalyst for coupling reactions in water under
heterogeneous and aerobic conditions with high recyclability [14, 15]. Palladium complexes
1