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Synthesis of Cr(III) Salen Complexes as Supramolecular Catalytic Systems for Ring-Opening Reactions of Epoxides

Lindbäck, Emil LU ; Norouzi-Arasi, Hassan LU ; Sheibani, Esmaeil LU ; Ma, Dayou LU ; Dawaigher, Sami LU and Wärnmark, Kenneth LU (2016) In ChemistrySelect 1(8). p.1789-1794
Abstract

The synthesis of two conformationally restricted Cr(III) salen complexes, 2 and 3, is described. Together, they constitute a supramolecular hydrogen-bonding catalytic system for the recently reported asymmetric ring-opening reactions of epoxides by a dynamic supramolecular catalyst. The synthesis involves state-of-the art transformations in frontline synthetic chemistry applied to heterocyclic chemistry. Hence, palladium-catalyzed reactions were employed, including carbonylative annelation and Suzuki cross-coupling reactions, for the formation of one of the heterocyclic rings (quinolone) and the functionalization of the formed rings. For the construction of the second heterocyclic ring (isoquinolone), a Curtius rearrangement was... (More)

The synthesis of two conformationally restricted Cr(III) salen complexes, 2 and 3, is described. Together, they constitute a supramolecular hydrogen-bonding catalytic system for the recently reported asymmetric ring-opening reactions of epoxides by a dynamic supramolecular catalyst. The synthesis involves state-of-the art transformations in frontline synthetic chemistry applied to heterocyclic chemistry. Hence, palladium-catalyzed reactions were employed, including carbonylative annelation and Suzuki cross-coupling reactions, for the formation of one of the heterocyclic rings (quinolone) and the functionalization of the formed rings. For the construction of the second heterocyclic ring (isoquinolone), a Curtius rearrangement was employed. The corresponding salen ligands were then prepared by Schiff-base reactions, yielding the final complexes after metal insertion. For reference purposes the less conformationally restricted Cr(III) complexes 4 and 5 were also synthesized.

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organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
isoquinolinone, quinolinone, salen, Supramolecular chemistry, synthesis
in
ChemistrySelect
volume
1
issue
8
pages
6 pages
publisher
Wiley-Blackwell
external identifiers
  • scopus:85027058814
ISSN
2365-6549
DOI
10.1002/slct.201600457
language
English
LU publication?
yes
id
af015512-316f-4883-bc20-4ab6e89736a5
date added to LUP
2020-04-22 14:38:54
date last changed
2023-09-10 03:32:56
@article{af015512-316f-4883-bc20-4ab6e89736a5,
  abstract     = {{<p>The synthesis of two conformationally restricted Cr(III) salen complexes, 2 and 3, is described. Together, they constitute a supramolecular hydrogen-bonding catalytic system for the recently reported asymmetric ring-opening reactions of epoxides by a dynamic supramolecular catalyst. The synthesis involves state-of-the art transformations in frontline synthetic chemistry applied to heterocyclic chemistry. Hence, palladium-catalyzed reactions were employed, including carbonylative annelation and Suzuki cross-coupling reactions, for the formation of one of the heterocyclic rings (quinolone) and the functionalization of the formed rings. For the construction of the second heterocyclic ring (isoquinolone), a Curtius rearrangement was employed. The corresponding salen ligands were then prepared by Schiff-base reactions, yielding the final complexes after metal insertion. For reference purposes the less conformationally restricted Cr(III) complexes 4 and 5 were also synthesized.</p>}},
  author       = {{Lindbäck, Emil and Norouzi-Arasi, Hassan and Sheibani, Esmaeil and Ma, Dayou and Dawaigher, Sami and Wärnmark, Kenneth}},
  issn         = {{2365-6549}},
  keywords     = {{isoquinolinone; quinolinone; salen; Supramolecular chemistry; synthesis}},
  language     = {{eng}},
  number       = {{8}},
  pages        = {{1789--1794}},
  publisher    = {{Wiley-Blackwell}},
  series       = {{ChemistrySelect}},
  title        = {{Synthesis of Cr(III) Salen Complexes as Supramolecular Catalytic Systems for Ring-Opening Reactions of Epoxides}},
  url          = {{http://dx.doi.org/10.1002/slct.201600457}},
  doi          = {{10.1002/slct.201600457}},
  volume       = {{1}},
  year         = {{2016}},
}