Palladium-bis(oxazoline) complexes with inherent chirality: Synthesis, crystal structures and applications in Suzuki, Heck and Sonogashira coupling reactions

S. M. Shakil Hussain; Mansur B. Ibrahim; Atif Fazal; Rami Suleiman; Mohammed Fettouhi; Bassam El Ali

doi:10.1016/j.poly.2013.12.023

Palladium-bis(oxazoline) complexes with inherent chirality: Synthesis, crystal structures and applications in Suzuki, Heck and Sonogashira coupling reactions

S. M. Shakil Hussain, Mansur B. Ibrahim, Atif Fazal, Rami Suleiman, Mohammed Fettouhi, Bassam El Ali^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

48 Scopus citations

Abstract

New palladium-bis(oxazoline) (Pd-BOX) complexes were synthesized and characterized. The X-ray crystal structures of the two complexes showed that the palladium ion is bound to the nitrogen atoms of the two heterocycles of the bidentate ligand and two chloride ions in a distorted square planar geometry. The coordination to the palladium ion allows these non C₂-symmetric bis(oxazoline) ligand-based complexes to acquire a rigid backbone curvature generating an inherent chirality. The catalytic activities were evaluated in Suzuki-Miyaura, Mizoroki-Heck and Sonogashira coupling reactions. The complexes showed high catalytic activities towards numerous C-C coupling reactions with various aryl halides, aryl boronic acids, alkenes and alkynes. The reactions were optimized for the most suitable temperature, solvent, and base system.

Original language	English
Pages (from-to)	39-46
Number of pages	8
Journal	Polyhedron
Volume	70
DOIs	https://doi.org/10.1016/j.poly.2013.12.023
State	Published - 9 Mar 2014

Bibliographical note

Funding Information:
The authors would like to acknowledge the support provided by King Abdulaziz City for Science and Technology (KACST) through the Science & Technology Unit at King Fahd University of Petroleum & Minerals (KFUPM) for funding this work through project No. 11-PET1665-04. as part of the National Science, Technology and Innovation Plan.

Keywords

Bis(oxazoline)
Coupling reactions
Inherent chirality
Palladium

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.poly.2013.12.023

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title = "Palladium-bis(oxazoline) complexes with inherent chirality: Synthesis, crystal structures and applications in Suzuki, Heck and Sonogashira coupling reactions",

abstract = "New palladium-bis(oxazoline) (Pd-BOX) complexes were synthesized and characterized. The X-ray crystal structures of the two complexes showed that the palladium ion is bound to the nitrogen atoms of the two heterocycles of the bidentate ligand and two chloride ions in a distorted square planar geometry. The coordination to the palladium ion allows these non C2-symmetric bis(oxazoline) ligand-based complexes to acquire a rigid backbone curvature generating an inherent chirality. The catalytic activities were evaluated in Suzuki-Miyaura, Mizoroki-Heck and Sonogashira coupling reactions. The complexes showed high catalytic activities towards numerous C-C coupling reactions with various aryl halides, aryl boronic acids, alkenes and alkynes. The reactions were optimized for the most suitable temperature, solvent, and base system.",

keywords = "Bis(oxazoline), Coupling reactions, Inherent chirality, Palladium",

author = "\{Shakil Hussain\}, \{S. M.\} and Ibrahim, \{Mansur B.\} and Atif Fazal and Rami Suleiman and Mohammed Fettouhi and \{El Ali\}, Bassam",

note = "Funding Information: The authors would like to acknowledge the support provided by King Abdulaziz City for Science and Technology (KACST) through the Science \& Technology Unit at King Fahd University of Petroleum \& Minerals (KFUPM) for funding this work through project No. 11-PET1665-04. as part of the National Science, Technology and Innovation Plan. ",

year = "2014",

month = mar,

day = "9",

doi = "10.1016/j.poly.2013.12.023",

language = "English",

volume = "70",

pages = "39--46",

journal = "Polyhedron",

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T1 - Palladium-bis(oxazoline) complexes with inherent chirality

T2 - Synthesis, crystal structures and applications in Suzuki, Heck and Sonogashira coupling reactions

AU - Shakil Hussain, S. M.

AU - Ibrahim, Mansur B.

AU - Fazal, Atif

AU - Suleiman, Rami

AU - Fettouhi, Mohammed

AU - El Ali, Bassam

N1 - Funding Information: The authors would like to acknowledge the support provided by King Abdulaziz City for Science and Technology (KACST) through the Science & Technology Unit at King Fahd University of Petroleum & Minerals (KFUPM) for funding this work through project No. 11-PET1665-04. as part of the National Science, Technology and Innovation Plan.

PY - 2014/3/9

Y1 - 2014/3/9

N2 - New palladium-bis(oxazoline) (Pd-BOX) complexes were synthesized and characterized. The X-ray crystal structures of the two complexes showed that the palladium ion is bound to the nitrogen atoms of the two heterocycles of the bidentate ligand and two chloride ions in a distorted square planar geometry. The coordination to the palladium ion allows these non C2-symmetric bis(oxazoline) ligand-based complexes to acquire a rigid backbone curvature generating an inherent chirality. The catalytic activities were evaluated in Suzuki-Miyaura, Mizoroki-Heck and Sonogashira coupling reactions. The complexes showed high catalytic activities towards numerous C-C coupling reactions with various aryl halides, aryl boronic acids, alkenes and alkynes. The reactions were optimized for the most suitable temperature, solvent, and base system.

AB - New palladium-bis(oxazoline) (Pd-BOX) complexes were synthesized and characterized. The X-ray crystal structures of the two complexes showed that the palladium ion is bound to the nitrogen atoms of the two heterocycles of the bidentate ligand and two chloride ions in a distorted square planar geometry. The coordination to the palladium ion allows these non C2-symmetric bis(oxazoline) ligand-based complexes to acquire a rigid backbone curvature generating an inherent chirality. The catalytic activities were evaluated in Suzuki-Miyaura, Mizoroki-Heck and Sonogashira coupling reactions. The complexes showed high catalytic activities towards numerous C-C coupling reactions with various aryl halides, aryl boronic acids, alkenes and alkynes. The reactions were optimized for the most suitable temperature, solvent, and base system.

KW - Bis(oxazoline)

KW - Coupling reactions

KW - Inherent chirality

KW - Palladium

UR - https://www.scopus.com/pages/publications/84892770433

U2 - 10.1016/j.poly.2013.12.023

DO - 10.1016/j.poly.2013.12.023

M3 - Article

AN - SCOPUS:84892770433

SN - 0277-5387

VL - 70

SP - 39

EP - 46

JO - Polyhedron

JF - Polyhedron

ER -

Palladium-bis(oxazoline) complexes with inherent chirality: Synthesis, crystal structures and applications in Suzuki, Heck and Sonogashira coupling reactions

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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