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Palladium-Catalyzed Carbocyclizations of Allenes with Unsaturated Hydrocarbons
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2004 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Palladium-catalyzed reactions of unsaturated hydrocarbons are important processes in organic chemistry especially for the generation of ring systems. This thesis describes the development and mechanistic studies of carbocyclization reactions of allenes with olefins, allyls or 1,3-dienes catalyzed by palladium(0)- and palladium(II)-complexes. These reactions generally exhibit high stereo- and regioselectivity and give rise to stereodefined [n,3,0] bicyclic systems (n=3,4,5,6) in good to excellent yields. The mechanisms for these reactions were investigated with special attention directed to the intramolecular reaction of (π-allyl)palladium(II)-complexes and (π-1,3-diene)palladium(II)-complexes with allenes. It was demonstrated that the carbon-carbon bond formation occurred by nucleophilic attack of the middle carbon atom of the allene on the face of the allyl or 1,3-diene opposite to that of the palladium atom. Further, two new types of oxidative palladium(II)-catalyzed reactions between allenes and olefins or 1,3-dienes have been developed. These cyclizations constitute a new type of carbon-carbon bond forming reaction and there are support for a palladium(II)-catalyzed C-H activation at the allenic moiety rendering a vinylidienepalladium-intermediate followed by carbon-carbon bond formation via insertion of the olefin or 1,3-diene.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi , 2004. , 53 p.
Keyword [en]
Palladium-catalysis, Allenes
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-100ISBN: 91-7265-863-0 (print)OAI: oai:DiVA.org:su-100DiVA: diva2:189150
Public defence
2004-04-29, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
Opponent
Supervisors
Available from: 2004-04-07 Created: 2004-04-07Bibliographically approved
List of papers
1. Stereoselective Palladium-Catalyzed Carbocyclization of Allenic Allylic Carboxylates.
Open this publication in new window or tab >>Stereoselective Palladium-Catalyzed Carbocyclization of Allenic Allylic Carboxylates.
2003 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, Vol. 125, no 46, 14140-14148 p.Article in journal (Refereed) Published
Identifiers
urn:nbn:se:su:diva-22601 (URN)
Note
Part of urn:nbn:se:su:diva-100Available from: 2004-04-07 Created: 2004-04-07 Last updated: 2009-10-07Bibliographically approved
2. Allenes as Carbon Nucleophiles in Intramolecular Attack on (π-1,3-diene)Palladium Complexes: Evidence for trans-Carbopalladation of the 1,3-Diene
Open this publication in new window or tab >>Allenes as Carbon Nucleophiles in Intramolecular Attack on (π-1,3-diene)Palladium Complexes: Evidence for trans-Carbopalladation of the 1,3-Diene
Show others...
2003 (English)In: Chemistry - A European Journal, ISSN 0947-6539, Vol. 9, no 14, 3445-3449 p.Article in journal (Refereed) Published
Identifiers
urn:nbn:se:su:diva-22602 (URN)
Note
Part of urn:nbn:se:su:diva-100Available from: 2004-04-07 Created: 2004-04-07 Last updated: 2010-01-13Bibliographically approved
3. Carbon-Carbon bond formation in Palladium(II)-Catalyzed Allylic Oxidation: A Novel Oxidative Carbozyclization of Allene-Substituted Olefins
Open this publication in new window or tab >>Carbon-Carbon bond formation in Palladium(II)-Catalyzed Allylic Oxidation: A Novel Oxidative Carbozyclization of Allene-Substituted Olefins
2003 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 125, no 20, 6056-6057 p.Article in journal (Refereed) Published
Identifiers
urn:nbn:se:su:diva-22603 (URN)10.1021/ja029505a (DOI)
Note
Part of urn:nbn:se:su:diva-100Available from: 2004-04-07 Created: 2004-04-07 Last updated: 2010-06-21Bibliographically approved
4. Allenes as Carbon Nucleophiles in Palladium-Catalyzed Reactions: Observation of anti Attack of Allenes on (p-Allyl)Palladium Complexes
Open this publication in new window or tab >>Allenes as Carbon Nucleophiles in Palladium-Catalyzed Reactions: Observation of anti Attack of Allenes on (p-Allyl)Palladium Complexes
2002 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 124, no 38, 11246-11247 p.Article in journal (Refereed) Published
Identifiers
urn:nbn:se:su:diva-22604 (URN)10.1021/ja026150m (DOI)
Note
Part of urn:nbn:se:su:diva-100Available from: 2004-04-07 Created: 2004-04-07 Last updated: 2010-06-21Bibliographically approved
5. Carbon-Carbon Bond Formation in Regio- and Stereoselective Palladium-Catalyzed Cyclization of Allene-Substituted Conjugated Dienes
Open this publication in new window or tab >>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
Identifiers
urn:nbn:se:su:diva-22605 (URN)
Note
Part of urn:nbn:se:su:diva-100Available from: 2004-04-07 Created: 2004-04-07 Last updated: 2010-06-21Bibliographically approved
6. Palladium(0)-Catalyzed Cycloisomerization of Enallenes.
Open this publication in new window or tab >>Palladium(0)-Catalyzed Cycloisomerization of Enallenes.
Manuscript (Other academic)
Identifiers
urn:nbn:se:su:diva-22606 (URN)
Note
Part of urn:nbn:se:su:diva-100Available from: 2004-04-07 Created: 2004-04-07 Last updated: 2010-01-13Bibliographically approved

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