Issue 20, 2010
From the journal:

Organic & Biomolecular Chemistry

Arenediazonium tetrafluoroborates in palladium-catalyzed C–P bond-forming reactions. Synthesis of arylphosphonates, -phosphine oxides, and -phosphines†

Roberta Berrino,a   Sandro Cacchi,*a   Giancarlo Fabrizi,a   Antonella Goggiamania  and  Paolo Stabileb  

* Corresponding authors

a Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza, Università di Roma, P.le A. Moro 5, Italy
E-mail: sandro.cacchi@uniroma1.it
Fax: +39-06-4991-2780
Tel: +39-06-4991-2795

b Chemical Development Department, GlaxoSmithKline, Via Fleming 4, Italy

Abstract

A novel palladium-catalyzed synthesis of arylphosphonates from arenediazonium tetrafluoroborates and triethylphosphite or diethylphosphite is presented. The reaction tolerates useful substituents including bromo, chloro, nitro, ether, cyano, keto, and ester groups, can be performed as a one-pot process from anilines omitting the isolation of arenediazonium salts, and can be extended to the preparation of arylphosphine oxides and arylphosphines.

Graphical abstract: Arenediazonium tetrafluoroborates in palladium-catalyzed C–P bond-forming reactions. Synthesis of arylphosphonates, -phosphine oxides, and -phosphines

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Article information

DOI
https://doi.org/10.1039/C0OB00243G
Article type
Communication
Submitted
10 Jun 2010
Accepted
28 Jul 2010
First published
13 Aug 2010

Org. Biomol. Chem., 2010,8, 4518-4520

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Arenediazonium tetrafluoroborates in palladium-catalyzed C–P bond-forming reactions. Synthesis of arylphosphonates, -phosphine oxides, and -phosphines

R. Berrino, S. Cacchi, G. Fabrizi, A. Goggiamani and P. Stabile, Org. Biomol. Chem., 2010, 8, 4518 DOI: 10.1039/C0OB00243G

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