Development of a highly selective and efficient catalyst for 1,3-butadiene dimerization

Surendra Harkal; Ralf Jackstell; Franz Nierlich; Dagmara Ortmann; Matthias Beller

doi:10.1021/ol048025g

Development of a highly selective and efficient catalyst for 1,3-butadiene dimerization

Org Lett. 2005 Feb 17;7(4):541-4. doi: 10.1021/ol048025g.

Authors

Surendra Harkal¹, Ralf Jackstell, Franz Nierlich, Dagmara Ortmann, Matthias Beller

Affiliation

¹ Leibniz-Institut für Organische Katalyse (IfOK) an der Universität Rostock e.V., Buchbinderstrasse 5-6, D-18055 Rostock, Germany.

PMID: 15704889
DOI: 10.1021/ol048025g

Abstract

A selective dimerization reaction of 1,3-butadiene in the presence of 2-propanol to give 1,3,7-octatriene has been developed. By modification of palladium carbene catalysts an unexpected selectivity switch from the telomerization to the dimerization product occurred. In applying the 1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-3H-imidazolidenylpalladium(0) complex 9, unprecedented catalyst efficiency (TON > 80 000 and TOF > 5000 h(-1)) has been obtained for this transformation. [reaction: see text]