Methodologies for the synthesis of highly substituted N-hydroxyphthalimides, towards new aerobic oxidation catalysts.
type: Dataset
description: In the chemical industry, oxidation reactions are not often performed in green chemistry conditions. Our group has been studying N-hydroxyphthalimides (NHPI) catalysts for the aerobic oxidation of various organic substrates in mild conditions. In order to obtain more active catalysts, two families of analogs, showing high substitution on the phthalimide core, have been prepared, following two new synthetic methodologies. The first one consists of the bis-ortho-metalation / silylation of unprotected ortho-phthalic acids, for the efficient access to silylated analogs of NHPI. Preliminary tests in aerobic oxidation catalysis show an interesting influence of the bulkiness of the silyl groups towards the active species, because of increases in catalytic activities. The second strategy includes a totally intramolecular [2+2+2] cyclotrimerization of ene-diyne diesters, affording an innovative pentacyclic bis-ortho-lactone scaffold. These intermediates are easily converted to 3,6-bis(2-hydroxyphenyl)-4,5-diarylphthalimides, which present C2 symmetry and two atropoisomeric axis. The resolution of both enantiomers has been performed, in order to access aerobic oxidation catalysts with potent enantioselective activity.
landing page: https://theses.hal.science/tel-00870768
identifier: NNT: 2012GRENV071
keyword: aerobic-oxidation
keyword: atropoisomerie
keyword: atropoisomerism
keyword: catalyse
keyword: catalysis
keyword: cyclotrimerisation
keyword: cyclotrimerization
keyword: infoeu-reposemanticsdoctoralthesis
keyword: nhpi
keyword: ortho-metalation
keyword: ortho-metallation
keyword: oxydation-aerobie
keyword: sdvsalife-sciences-q-bioagricultural-sciences
keyword: theses
issued: 2026-05-09T11:01:04.909744
modified: 2026-05-09T11:01:04.909749
language: fr
contact point: Organization
  fn: CCSD

test_moissonnage_selune
type: Agent

Methodologies for the synthesis of highly substituted N-hydroxyphthalimides, towards new aerobic oxidation catalysts.
type: Distribution
format: HTML
access URL: https://theses.hal.science/tel-00870768
issued: 2026-05-09T11:01:04.917148
modified: 2026-05-09T11:01:04.891008