3-Aryl Substituted 1-Methylquinolinium Salts as Carbene Precursors

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Batsyts , S , Vedmid , R , Namyslo , J C , Nieger , M & Schmidt , A 2019 , ' 3-Aryl Substituted 1-Methylquinolinium Salts as Carbene Precursors ' , European Journal of Organic Chemistry , no. 6 , pp. 1301-1310 . https://doi.org/10.1002/ejoc.201801648

Title: 3-Aryl Substituted 1-Methylquinolinium Salts as Carbene Precursors
Author: Batsyts, Sviatoslav; Vedmid, Roman; Namyslo, Jan C.; Nieger, Martin; Schmidt, Andreas
Contributor: University of Helsinki, Department of Chemistry
Date: 2019-02-14
Language: eng
Number of pages: 10
Belongs to series: European Journal of Organic Chemistry
ISSN: 1434-193X
URI: http://hdl.handle.net/10138/324829
Abstract: 1-Methylquinolinium salts substituted at the C3 position with phenyl, naphthalen-1-yl, phenanthren-9-yl, and pentaphenyl phenyl as well as aryl ethynyl substituents were prepared. The phenyl, naphthalen-1-yl, and phenanthren-9-yl substituents are in conjugation with the quinolinium ring, and the sterically crowded pentaphenyl phenyl residue causes a propeller-type molecule possessing a calculated dihedral angle between aryl substituent and the quinolinium ring of approximately 54 degrees. The different influences of the substituents including the aryl ethynyl residues on the pi-architecture is well reflected in their frontier orbital profiles, their spectroscopic properties, and in their ability to form N-heterocyclic carbenes. The latter were generated from the C3-aryl substituted quinolinium salts and trapped as sulfur and selenium adducts, whereas the aryl ethynyl substituted derivatives failed to undergo the NHC generation under the conditions applied. Se-77 NMR measurements of the corresponding selenones reveal that quinolin-2-ylidenes are electron poor carbenes with strong pi-acceptor character.
Subject: Quinoline
Carbenes
Selenones
Heterocycle synthesis
Quinolin-2-ylidene
N-HETEROCYCLIC CARBENE
PALLADIUM COMPLEXES
DECARBOXYLATION
PYRIDINYLIDENE
ISOMERIZATION
INTERMEDIATE
QUINOLINIUM
GENERATION
116 Chemical sciences
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