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New Functionalized Vinyl Monomers by Ethylene-(Functionalized)-Norbornene Hetero-Trimerization Catalyzed by Cobalt(II)-(Imino)pyridine Complexes

  1. Alessandro Toti,
  2. Giuliano Giambastiani,
  3. Claudio Bianchini,
  4. Andrea Meli,
  5. Lapo Luconi

Article first published online: 24 JUL 2008

DOI: 10.1002/adsc.200800201

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 350, Issue 11-12, pages 1855–1866, August 4, 2008

Additional Information

How to Cite

Toti, A., Giambastiani, G., Bianchini, C., Meli, A. and Luconi, L. (2008), New Functionalized Vinyl Monomers by Ethylene-(Functionalized)-Norbornene Hetero-Trimerization Catalyzed by Cobalt(II)-(Imino)pyridine Complexes. Adv. Synth. Catal., 350: 1855–1866. doi: 10.1002/adsc.200800201

Author Information

  1. Istituto di Chimica dei Composti Organometallici (ICCOM – CNR), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Firenze, Italy, Fax: (+39)-055-522-5203

Publication History

  1. Issue published online: 31 JUL 2008
  2. Article first published online: 24 JUL 2008
  3. Manuscript Revised: 19 JUN 2008
  4. Manuscript Received: 2 APR 2008

Funded by

  • European Commission. Grant Numbers: NoE IDECAT, NMP3-CT-2005–011730, NMP3-CT-2005–516972
  • Ministero dell′Istruzione, dell′Università e della Ricerca of Italy. Grant Number: RBNE03R78E

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Keywords:

  • cobalt catalysis;
  • co-oligomerization;
  • ethylene-norbornene;
  • (imino)pyridine ligands;
  • vinyl monomers

Abstract

On activation by MAO the (imino)pyridine cobalt(II) complex CoCl2N2math image catalyzes the enchainment of one norbornene (NB) molecule with two ethylene molecules to give exo-2,exo-3-ethylvinylnorbornane with high activity and complete diastereoselectivity. Turnover frequencies [TOF, mol NB (mol Co×h)−1] as high as 270,000 have been obtained. The 2E-1NB hetero-trimerization reaction has been also accomplished with NBs bearing polar substituents such as norbornenemethanol and norbornenecarboxylic acid provided that the substrate is protected with triisobutylaluminum and the less sterically demanding complex CoCl2N2math image is used as catalyst precursor. A mechanism for the hetero-trimerization reactions is proposed on the basis of experimental evidence.

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