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Palladium-Catalyzed Carbocyclizations of Allenes with Unsaturated Hydrocarbons
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
2004 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Stockholm: Institutionen för organisk kemi , 2004. , s. 53
Emneord [en]
Palladium-catalysis, Allenes
HSV kategori
Identifikatorer
URN: urn:nbn:se:su:diva-100ISBN: 91-7265-863-0 (tryckt)OAI: oai:DiVA.org:su-100DiVA, id: diva2:189150
Disputas
2004-04-29, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 14:00
Opponent
Veileder
Tilgjengelig fra: 2004-04-07 Laget: 2004-04-07bibliografisk kontrollert
Delarbeid
1. Stereoselective Palladium-Catalyzed Carbocyclization of Allenic Allylic Carboxylates.
Åpne denne publikasjonen i ny fane eller vindu >>Stereoselective Palladium-Catalyzed Carbocyclization of Allenic Allylic Carboxylates.
2003 (engelsk)Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 125, nr 46, s. 14140-14148Artikkel i tidsskrift (Fagfellevurdert) Published
Identifikatorer
urn:nbn:se:su:diva-22601 (URN)
Merknad
Part of urn:nbn:se:su:diva-100Tilgjengelig fra: 2004-04-07 Laget: 2004-04-07 Sist oppdatert: 2017-12-13bibliografisk kontrollert
2. Allenes as Carbon Nucleophiles in Intramolecular Attack on (π-1,3-diene)Palladium Complexes: Evidence for trans-Carbopalladation of the 1,3-Diene
Åpne denne publikasjonen i ny fane eller vindu >>Allenes as Carbon Nucleophiles in Intramolecular Attack on (π-1,3-diene)Palladium Complexes: Evidence for trans-Carbopalladation of the 1,3-Diene
Vise andre…
2003 (engelsk)Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 9, nr 14, s. 3445-3449Artikkel i tidsskrift (Fagfellevurdert) Published
Identifikatorer
urn:nbn:se:su:diva-22602 (URN)
Merknad
Part of urn:nbn:se:su:diva-100Tilgjengelig fra: 2004-04-07 Laget: 2004-04-07 Sist oppdatert: 2017-12-13bibliografisk kontrollert
3. Carbon-Carbon bond formation in Palladium(II)-Catalyzed Allylic Oxidation: A Novel Oxidative Carbozyclization of Allene-Substituted Olefins
Åpne denne publikasjonen i ny fane eller vindu >>Carbon-Carbon bond formation in Palladium(II)-Catalyzed Allylic Oxidation: A Novel Oxidative Carbozyclization of Allene-Substituted Olefins
2003 (engelsk)Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 125, nr 20, s. 6056-6057Artikkel i tidsskrift (Fagfellevurdert) Published
Identifikatorer
urn:nbn:se:su:diva-22603 (URN)10.1021/ja029505a (DOI)
Merknad
Part of urn:nbn:se:su:diva-100Tilgjengelig fra: 2004-04-07 Laget: 2004-04-07 Sist oppdatert: 2017-12-13bibliografisk kontrollert
4. Allenes as Carbon Nucleophiles in Palladium-Catalyzed Reactions: Observation of anti Attack of Allenes on (p-Allyl)Palladium Complexes
Åpne denne publikasjonen i ny fane eller vindu >>Allenes as Carbon Nucleophiles in Palladium-Catalyzed Reactions: Observation of anti Attack of Allenes on (p-Allyl)Palladium Complexes
2002 (engelsk)Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 124, nr 38, s. 11246-11247Artikkel i tidsskrift (Fagfellevurdert) Published
Identifikatorer
urn:nbn:se:su:diva-22604 (URN)10.1021/ja026150m (DOI)
Merknad
Part of urn:nbn:se:su:diva-100Tilgjengelig fra: 2004-04-07 Laget: 2004-04-07 Sist oppdatert: 2017-12-13bibliografisk kontrollert
5. Carbon-Carbon Bond Formation in Regio- and Stereoselective Palladium-Catalyzed Cyclization of Allene-Substituted Conjugated Dienes
Åpne denne publikasjonen i ny fane eller vindu >>Carbon-Carbon Bond Formation in Regio- and Stereoselective Palladium-Catalyzed Cyclization of Allene-Substituted Conjugated Dienes
2001 (engelsk)Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 66, nr 24, s. 8015-8025Artikkel i tidsskrift (Fagfellevurdert) Published
Identifikatorer
urn:nbn:se:su:diva-22605 (URN)
Merknad
Part of urn:nbn:se:su:diva-100Tilgjengelig fra: 2004-04-07 Laget: 2004-04-07 Sist oppdatert: 2017-12-13bibliografisk kontrollert
6. Palladium(0)-Catalyzed Cycloisomerization of Enallenes.
Åpne denne publikasjonen i ny fane eller vindu >>Palladium(0)-Catalyzed Cycloisomerization of Enallenes.
Manuskript (Annet vitenskapelig)
Identifikatorer
urn:nbn:se:su:diva-22606 (URN)
Merknad
Part of urn:nbn:se:su:diva-100Tilgjengelig fra: 2004-04-07 Laget: 2004-04-07 Sist oppdatert: 2010-01-13bibliografisk kontrollert

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