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Carbon-carbon bond formation in regio- and stereoselective palladium-catalyzed cyclization of allene-substituted conjugated dienes
2001 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 66, no 24, 8015-8025 p.Article in journal (Refereed) Published
Abstract [en]

Regio- and stereoselective palladium-catalyzed reactions of allene-substituted 1,3-dienes 1 in acetic acid at room temperature lead to cyclization with formation of a carbon-carbon bond between the middle carbon of the allene and the terminal carbon of the 1,3-diene. Two different types of reactions, both that constitute 1,4-carboacetoxylations of the 1,3-diene, have been developed. In one of the reactions, Pd(II) catalyzes the oxidation of 1 to bicyclic compounds 2, and in the other, Pd(0) catalyzes the transformation of 1 to bicyclic compounds 3. The products 2 are useful for further synthetic transformations and undergo Diels-Alder reactions with dienophiles to give polycyclic ring systems.

Place, publisher, year, edition, pages
2001. Vol. 66, no 24, 8015-8025 p.
Keyword [en]
(ETA-1, ETA-3-OCTADIENEDIYL)PALLADIUM COMPLEXES, INTRAMOLECULAR 1, 2-OXIDATION, ELECTRON-TRANSFER, 1, 3-DIENES, 1, 4-OXIDATION, CARBOPALLADATION, HETEROANNULATION, TRANSFORMATIONS, NUCLEOPHILES, REAGENT
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-24324DOI: 10.1021/jo0157324ISI: 000172489500012OAI: oai:DiVA.org:kth-24324DiVA: diva2:346562
Note
QC 20100901Available from: 2010-09-01 Created: 2010-09-01 Last updated: 2017-12-12Bibliographically approved

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Franzén, Johan

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