Kellner, Dominik and Weger, Maximilian and Gini, Andrea and Mancheno, Olga Garcia (2017) Pd(OAc)(2)/Ph3P-catalyzed dimerization of isoprene and synthesis of monoterpenic heterocycles. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 13. pp. 1807-1815. ISSN 1860-5397,
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The palladium-catalyzed dimerization of isoprene is a practical approach of synthesizing monoterpenes. Though several highly selective methods have been reported, most of them still required pressure or costly ligands for attaining the active system and desired selectivity. Herein, we present a simple and economical procedure towards the tail-to-tail dimer using readily available Pd(OAc)(2) and inexpensive triphenylphosphine as ligand. Furthermore, simple screw cap vials are employed, allowing carrying out the reaction at low pressure. In addition, the potential of the dimer as a chemical platform for the preparation of heterocyclic terpenes by subsequent (hetero)-Diels-Alder or [4 + 1]-cycloadditions with nitrenes is also depicted.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PALLADIUM-CATALYZED REACTIONS; (ETA-1,ETA-3-OCTADIENEDIYL)PALLADIUM COMPLEXES; CARBENE CATALYSTS; 1,3-DIENES; TELOMERIZATION; BUTADIENE; TETRAMERIZATION; OLIGOMERIZATION; NUCLEOPHILES; DERIVATIVES; dimerization; heterocycles; isoprene; monoterpene; palladium catalysis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Olga Garcia Mancheño |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Dec 2018 13:15 |
| Last Modified: | 01 Mar 2019 06:40 |
| URI: | https://pred.uni-regensburg.de/id/eprint/1356 |
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