Issue 30, 2013
From the journal:

Dalton Transactions

Reactivity differences between 2,4- and 2,5-disubstituted zirconacyclopentadienes: a highly selective and general approach to 2,4-disubstituted phospholes†

Guillaume Bousrez,a   Florian Jaroschik,*a   Agathe Martinez,a   Dominique Harakat,a   Emmanuel Nicolas,b   Xavier F. Le Goffb  and  Jan Szymoniak*a  

* Corresponding authors

a Institut de Chimie Moléculaire de Reims, UMR CNRS 7312, Université de Reims, BP 1039, 51687 Reims, France
E-mail: florian.jaroschik@univ-reims.fr, jan.szymoniak@univ-reims.fr
Fax: +33 326913166
Tel: +33 326913244

b Laboratoire “Hétéroéléments et Coordination”, Ecole Polytechnique and CNRS, 91128 Palaiseau Cedex, France

Abstract

Mixtures of 2,4- and 2,5-disubstituted zirconacyclopentadienes were obtained by the reductive dimerisation of terminal alkynes using the Cp2ZrCl2/lanthanum system. Reactions of dihalophosphines with these mixtures afforded selectively the corresponding 2,4-disubstituted phospholes and 1,4-disubstituted butadienes. A new series of phospholes was characterized by multi-nuclear NMR spectroscopy and X-ray analysis. A possible explanation for the observed selectivity was obtained from X-ray studies and DFT analysis of the intermediate zirconacyclopentadienes.

Graphical abstract: Reactivity differences between 2,4- and 2,5-disubstituted zirconacyclopentadienes: a highly selective and general approach to 2,4-disubstituted phospholes

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Article information

DOI
https://doi.org/10.1039/C3DT51158H
Article type
Paper
Submitted
03 May 2013
Accepted
31 May 2013
First published
31 May 2013

Dalton Trans., 2013,42, 10997-11004

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Reactivity differences between 2,4- and 2,5-disubstituted zirconacyclopentadienes: a highly selective and general approach to 2,4-disubstituted phospholes

G. Bousrez, F. Jaroschik, A. Martinez, D. Harakat, E. Nicolas, X. F. Le Goff and J. Szymoniak, Dalton Trans., 2013, 42, 10997 DOI: 10.1039/C3DT51158H

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