Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Palladium(0)-catalyzed benzylation of H-phosphonate diesters: An efficient entry to benzylphosphonates
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2009 (English)In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, no 2, 225-228 p.Article in journal (Refereed) Published
Abstract [en]

A new, efficient method for the synthesis of benzylphosphonate diesters via a palladium(0)-catalyzed cross-coupling reaction between benzyl halides and H-phosphonate diesters, using Pd(OAc)2 as a palladium source and Xantphos as a supporting ligand, has been developed.

Place, publisher, year, edition, pages
2009. no 2, 225-228 p.
Keyword [en]
benzylphosphonates, palladium cross-coupling, H-phos­phonates, C-phosphonates
National Category
Other Basic Medicine
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-26326DOI: 10.1055/s-0028-1087522ISI: 000262988100011OAI: oai:DiVA.org:su-26326DiVA: diva2:208538
Available from: 2009-03-18 Created: 2009-03-18 Last updated: 2010-04-28Bibliographically 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

Open Access in DiVA

No full text

Other links

Publisher's full text

Search in DiVA

By author/editor
Lavén, GastonStawinski, Jacek
By organisation
Department of Organic Chemistry
In the same journal
Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry
Other Basic Medicine

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 66 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf