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Palladium-Catalyzed Coupling of Allylboronic Acids with Iodobenzenes. Selective Formation of the Branched Allylic Product in the Absence of Directing Groups
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2006 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 128, no 25, 8150-8151 p.Article in journal (Refereed) Published
Abstract [en]

Palladium-catalyzed coupling reactions of functionalized allylboronic acids with iodobenzenes were achieved under standard Suzuki−Miyaura coupling conditions. The coupling reactions afforded selectively the branched allylic products in high to excellent yields. In contrast to palladium-catalyzed nucleophilic substitution reactions proceeding via (η3-allyl)palladium intermediates, this process does not require directing groups in the allyl moiety to achieve substitution at the congested allylic terminus. The regioselectivity of the process was largely unaffected by the substituent effects of the iodobenzenes and the allylic substrates.

Place, publisher, year, edition, pages
2006. Vol. 128, no 25, 8150-8151 p.
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-27802DOI: 10.1021/ja062585oOAI: oai:DiVA.org:su-27802DiVA: diva2:218357
Available from: 2009-05-19 Created: 2009-05-19 Last updated: 2017-12-13Bibliographically approved
In thesis
1. Development of New Synthetic Routes to Organoboronates by Catalytic Allylic Substitution and C-H bond Functionalization
Open this publication in new window or tab >>Development of New Synthetic Routes to Organoboronates by Catalytic Allylic Substitution and C-H bond Functionalization
2009 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis describes the development of new catalytic methods for the synthesis and application of organometallic reagents, mainly focusing on allylboronic acid derivatives. Thus, palladium pincer-complex catalysis has been applied for extending the scope of palladiumcatalyzed borylation reactions in the synthesis of regio- and stereodefined functionalized allylboronic acid derivatives. These novel allylboronic acids were also employed as substrates in palladium catalyzed regioselective coupling reactions with iodobenzenes. We have also developed a new one-pot sequence based on preparation of allyl- and vinylboronates

via catalytic carbon-hydrogen bond activation/borylation reactions. The synthetic scope of the reaction as well as mechanistic studies on the borylation process are presented. Finally, the synthesis of new chiral palladium pincer-complexes is described. These species were employed as catalysts in asymmetric electrophilic allyation of imines.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2009. 54 p.
Keyword
Palladium, Iridium, Boron, Catalysis
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-27753 (URN)978-91-7155-899-2 (ISBN)
Public defence
2009-06-11, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 13:00 (English)
Opponent
Supervisors
Available from: 2009-05-20 Created: 2009-05-15 Last updated: 2009-05-19Bibliographically approved

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