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Preparation of benzylphosphonates via a palladium(0)-catalyzed cross-coupling of H-phosphonate diesters with benzyl halides. Synthetic and mechanistic studies
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Jacek Stawinski)
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Jacek Stawinski)
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Jacek Stawinski)
Stockholm University, Faculty of Science, Department of Organic Chemistry. (Jacek Stawinski)
2010 (English)In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 34, no 5, 967-975 p.Article in journal (Refereed) Published
Abstract [en]

We have developed a new, efficient method for the synthesis of benzylphosphonate andbenzylphosphonothioate diesters via a palladium(0)-catalyzed cross-coupling reaction betweenbenzyl halides and H-phosphonate or H-phosphonothioate diesters, using Pd2(dba)3(CHCl3)as a palladium source and Xantphos as a supporting ligand. Some mechanistic aspects of thesereactions were investigated using 31P NMR spectroscopy.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2010. Vol. 34, no 5, 967-975 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-38775DOI: 10.1039/b9nj00585dISI: 000277399200022OAI: oai:DiVA.org:su-38775DiVA: diva2:315045
Funder
Swedish Research Council
Available from: 2010-04-28 Created: 2010-04-28 Last updated: 2017-12-12Bibliographically approved
In thesis
1. Expanding the H-phosphonate and H-phosphonothioate chemistry towards biologically important phosphate analogs
Open this publication in new window or tab >>Expanding the H-phosphonate and H-phosphonothioate chemistry towards biologically important phosphate analogs
2010 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis focuses on chemical transformations of H-phosphonate and H-phosphonothioate and can be divided in two parts. The first part, is devoted to the development of the palladium-catalyzed P-C bond formation. Both mechanistic and synthetic studies of the transformations have been performed. The stereochemical aspects of palladium catalyzed arylation and benzylation of DNA analogs containing H-phosphonate and H-phosphonothioate have been studied.

In chapter 5 the condensation using Mitsunobu reaction of H-phosphonate function and nucleoside has been studied. Efficient protocols for the synthesis of nucleoside H-phosphonate monoester were developed.

The last chapter deals with development of silylation-mediated transesterfication of phenyl H-phosphonothioate as a thiophosphonylating agent. The methodology was used to prepare nucleoside H-phosphonothioate monomeric building blocks in good yields.

Publisher
40 p.
Keyword
Phosphonate, phosphonothioate, H-phosphonate
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-37514 (URN)978-91-7447-020-8 (ISBN)
Public defence
2010-05-21, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 3: Accepted. Available from: 2010-04-29 Created: 2010-03-08 Last updated: 2010-04-28Bibliographically approved

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