Synlett 2013; 24(10): 1260-1262
DOI: 10.1055/s-0033-1338847
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© Georg Thieme Verlag Stuttgart · New York

Substituent Effects in NHC–Boranes: Reactivity Switch in the Nucleophilic Fluorination of NHC–Boranes

Malika Makhlouf Brahmi
a   UPMC Université Paris 06, IPCM (UMR 7201), 4 Pl. Jussieu, C. 229, 75005 Paris, France
,
Max Malacria
a   UPMC Université Paris 06, IPCM (UMR 7201), 4 Pl. Jussieu, C. 229, 75005 Paris, France
,
Dennis P. Curran
b   Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA
,
Louis Fensterbank
a   UPMC Université Paris 06, IPCM (UMR 7201), 4 Pl. Jussieu, C. 229, 75005 Paris, France
,
Emmanuel Lacôte*
a   UPMC Université Paris 06, IPCM (UMR 7201), 4 Pl. Jussieu, C. 229, 75005 Paris, France
c   Université de Lyon, Institut de chimie de Lyon, UMR 5265 CNRS-Université Lyon I-ESCPE Lyon, 43 Bd du 11 novembre 1918, 69616 Villeurbanne, France   Fax: +33(4)72431795   eMail: emmanuel.lacote@univ-lyon1.fr
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Publikationsverlauf

Received: 23. April 2013

Accepted after revision: 03. Mai 2013

Publikationsdatum:
28. Mai 2013 (online)


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Abstract

Substituents on the boron atom of NHC–boranes direct the reactivity of the ligated boreniums obtained through hydride abstraction. Depending on the electronics of the substituent, the reaction is selectively steered toward either B-substitution or Lewis base exchange.

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