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Issue 45, 2015
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C–F sp2 bond functionalization mediated by niobium complexes

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Abstract

Insertion chemistry of isocyanide molecules was used to functionalize C–F sp2 bonds after their oxidative addition across the metal center in a β-diketiminate niobium(III) imido complex (BDI)Nb(NtBu)(C6H6). The complexes formed, 3a–b ([BDI]Nb(PhC[double bond, length as m-dash]N)(NtBu)(F) (R = 1,6-diisopropylphenyl, tert-butyl), were characterized by NMR spectroscopy and X-ray analysis. Further treatment with phenylsilane induced H/F exchange under mild conditions, which was followed by hydride transfer to the inserted isocyanide. Divergent reactivity was observed when the two analogous aryl and tert-butyl isocyanide insertion products were treated with phenylsilane.

Graphical abstract: C–F sp2 bond functionalization mediated by niobium complexes

  • This article is part of the themed collection: Fluorine
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Supplementary files

Article information


Submitted
02 Jun 2015
Accepted
17 Jul 2015
First published
20 Jul 2015

Dalton Trans., 2015,44, 19494-19500
Article type
Paper

C–F sp2 bond functionalization mediated by niobium complexes

M. Nechayev, T. L. Gianetti, R. G. Bergman and J. Arnold, Dalton Trans., 2015, 44, 19494
DOI: 10.1039/C5DT02082D

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