Issue 5, 2010
From the journal:

New Journal of Chemistry

Preparation of benzylphosphonates via a palladium(0)-catalyzed cross-coupling of H-phosphonatediesters with benzyl halides. Synthetic and mechanistic studies†‡§

Gaston Lavén,a   Marcin Kalek,a   Martina Jezowskaa  and  Jacek Stawinski*ab  

* Corresponding authors

a Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden

b Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznan, Poland
E-mail: js@organ.su.se
Fax: +46 8 15 49 08

Abstract

We have developed a new, efficient method for the synthesis of benzylphosphonate and benzylphosphonothioate diesters via a palladium(0)-catalyzed cross-coupling reaction between benzyl 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 these reactions were investigated using 31P NMR spectroscopy.

Graphical abstract: Preparation of benzylphosphonates via a palladium(0)-catalyzed cross-coupling of H-phosphonate diesters with benzyl halides. Synthetic and mechanistic studies

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Article information

DOI
https://doi.org/10.1039/B9NJ00585D
Article type
Paper
Submitted
21 Oct 2009
Accepted
11 Dec 2009
First published
12 Feb 2010

New J. Chem., 2010,34, 967-975

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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

G. Lavén, M. Kalek, M. Jezowska and J. Stawinski, New J. Chem., 2010, 34, 967 DOI: 10.1039/B9NJ00585D

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