Issue 45, 2015

C–F sp2 bond functionalization mediated by niobium complexes

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

Supplementary files

Article information

Article type
Paper
Submitted
02 jun 2015
Accepted
17 jul 2015
First published
20 jul 2015

Dalton Trans., 2015,44, 19494-19500

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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