Deprotonation, insertion and isomerisation in the post-functionalisation of tris-pyridyl aluminates

Post-functionalisation of the aluminate anion [EtAl(6-R-2-py) 3 ] − (6-R-2-py = 6-R-2-pyridyl, R = Me or Br) can be accomplished via nucleophilic addition of the pyridyl groups to the electrophilic C&z.dbd;O group of aldehydes (RCH&z.dbd;O) or by deprotonation of carboxylic acids (RCO 2 H)....

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Published in:Dalton transactions : an international journal of inorganic chemistry 2019-04, Vol.48 (17), p.5692-5697
Main Authors: Plajer, Alex J, Kopf, Sara, Colebatch, Annie L, Bond, Andrew D, Wright, Dominic S, García-Rodríguez, Raúl
Format: Article
Language:English
Subjects:
Aldehydes
Aluminates
Carboxylic acids
Chirality
Crystal structure
Crystallography
Crystals
Isomerization
NMR
Nuclear magnetic resonance
Single crystals
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Summary:Post-functionalisation of the aluminate anion [EtAl(6-R-2-py) 3 ] − (6-R-2-py = 6-R-2-pyridyl, R = Me or Br) can be accomplished via nucleophilic addition of the pyridyl groups to the electrophilic C&z.dbd;O group of aldehydes (RCH&z.dbd;O) or by deprotonation of carboxylic acids (RCO 2 H). NMR spectroscopic and crystallographic studies show how 6-Me-2-py groups can detect chirality and reveal a new aspect of isomerism. Reactions of aluminate anions [EtAl(6-R-2-py) 3 ] − (6-R-2-py = 6-R-2-pyridyl, R = Me or Br) with aldehydes (RCH&z.dbd;O) or carboxylic acids (RCO 2 H) reveal how these species can be used to sense chirality and show a new aspect of isomerism in this area.
ISSN:1477-9226
1477-9234
DOI:10.1039/c9dt00869a