Synthesis of novel tantalacalixarene complexes: First example of intramolecular CH activation of monodepleted aromatic ring

Jeff Espinas, Jeremie Pelletier, Erwan Jeanneau, Ulrich Darbost, Kai C. Szeto, Christine Lucas, Jean Thivolle-Cazat, Christian Duchamp, Natali Henriques, Denis Bouchu, Jean-Marie Maurice Basset, Henry Chermette*, Isabelle Bonnamour, Mostafa Taoufik

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The alkylation of (dichlorotantala)-p-tert-butylcalix[4]arenes 1 and 3 by two equivalents of NpMgCl (Np = neopentyl) affords the corresponding unreported (bisneopentyltantala)-p-tert-butylcalix[4]arenes 4 and 5. These complexes can undergo dealkylation by modest increase of the temperature to yield 6 and 7. The characterization and structural conformation of the complexes 6 and 7 were determined by 1H, 13C, NOESY, and COSY spectroscopic studies and single-crystal X-ray diffraction. 7 exhibits unprecedented use of an intramolecular C-H activation of an aromatic ring and simultaneously releases of one equivalent of neopentane. DFT calculation supports a mechanism in which the metal passes through a transition state involving a coplanar arrangement with its three ligands (CAr, HAr, CNp).

Original languageEnglish (US)
Pages (from-to)3512-3521
Number of pages10
JournalOrganometallics
Volume30
Issue number13
DOIs
StatePublished - Jul 11 2011

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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