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Issue 7, 2015
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Consecutive C–F bond activation and C–F bond formation of heteroaromatics at rhodium: the peculiar role of FSi(OEt)3

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Abstract

C–F activation of 2,3,5,6-tetrafluoropyridine at [Rh{Si(OEt)3}(PEt3)3] (1) yields [Rh{2-(3,5,6-C5F3HN)}(PEt3)3] (2) and FSi(OEt)3, but in an unprecedented consecutive reaction FSi(OEt)3 acts as a fluoride source to give [Rh(4-C5F4N)(PEt3)3] (4) by regeneration of the C–F bond and C–H activation. Analogous refluorination steps were observed for other 2-pyridyl rhodium complexes. NMR spectroscopic studies revealed a delicate balance between the feasibility for C–F bond formation accompanied by a C–H activation and the occurrence of competing reactions such as hydrodefluorinations induced by the intermediary presence of H2.

Graphical abstract: Consecutive C–F bond activation and C–F bond formation of heteroaromatics at rhodium: the peculiar role of FSi(OEt)3

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Publication details

The article was received on 10 Mar 2015, accepted on 09 May 2015 and first published on 26 May 2015


Article type: Edge Article
DOI: 10.1039/C5SC00877H
Chem. Sci., 2015,6, 4255-4260
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    Consecutive C–F bond activation and C–F bond formation of heteroaromatics at rhodium: the peculiar role of FSi(OEt)3

    A. L. Raza and T. Braun, Chem. Sci., 2015, 6, 4255
    DOI: 10.1039/C5SC00877H

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