Synthesis of Cr(III) Salen Complexes as Supramolecular Catalytic Systems for Ring-Opening Reactions of Epoxides
(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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- author
- Lindbäck, Emil LU ; Norouzi-Arasi, Hassan LU ; Sheibani, Esmaeil LU ; Ma, Dayou LU ; Dawaigher, Sami LU and Wärnmark, Kenneth LU
- organization
- publishing date
- 2016
- 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}}, }