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

Gaston Lavén; Marcin Kalek; Martina Jezowska; Jacek Stawinski

doi:10.1039/B9NJ00585D

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

Gaston Lavén,^a Marcin Kalek,^a Martina Jezowska^a and Jacek Stawinski*^a^b

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* 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.

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Publication details

The article was received on 21 Oct 2009, accepted on 11 Dec 2009 and first published on 12 Feb 2010

Article type: Paper

DOI: 10.1039/B9NJ00585D

Citation: 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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New Journal of Chemistry

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

Abstract

Supplementary files

Publication details

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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