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Allenes as carbon nucleophiles in intramolecular attack on (pi-1,3-diene)palladium complexes: Evidence for trans carbopalladation of the 1,3-diene
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2003 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 9, no 14, 3445-3449 p.Article in journal (Refereed) Published
Abstract [en]

Reaction of allene-substituted cyclohexa- and cyclohepta-1,3-dienes with [PdCl2(PhCN)(2)] gave eta(3)-( 1,2,3)-cyclohexenyl- and eta(3)-(1,2,3)-cycloheptenylpalladium complexes. respectively. in which C-C bond formation between the allene and the 1.3-diene has occurred. Analysis of the (pi-allyl)palladium complexes by NMR spectroscopy. using reporter ligands, shows that the C-C bond formation has occurred by a trans carbopalladation involving nucleophilic attack by the middle carbon atom of the allene on a (pi-diene)palladium(n) complex. The stereochemistry of the (pi-allyl)palladium complexes was confirmed by benzoquinone-induced stereoselective transformations to allylic acetates.

Place, publisher, year, edition, pages
2003. Vol. 9, no 14, 3445-3449 p.
Keyword [en]
C-C coupling, carbopalladation, palladium, reaction mechanisms
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-24255DOI: 10.1002/chem.200305056ISI: 000184479300027OAI: oai:DiVA.org:kth-24255DiVA: diva2:346059
Note
QC 20100830Available from: 2010-08-30 Created: 2010-08-30 Last updated: 2017-12-12Bibliographically approved

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Franzén, Johan

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