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Solvent- and anion-dependent rearrangement of fluorinated carbene ligands provides access to fluorinated alkenes

Abstract

The construction of fluorocarbene ligands within the coordination sphere of transition metal complexes using sequential nucleophilic and electrophilic addition to a vinylidene complex is described. Reaction of [Ru(η5-C5H5)(dppe)(=C=CPhF)][N(SO2Ph)2] with [NMe4]F results in nucleophilic attack fluoride at the metal-bound carbon of the vinylidene ligand to give alkenyl complex [Ruη5-C5H5)(dppe)(-CF=CFPh)]. Subsequent eletrophilic fluorination with N-fluorobenzenesulfonimide (NFSI) results in the formation of the fluorinated carbene complex Ruη5-C5H5)(dppe)(=CF-CHFPh)][N(SO2Ph)2] . The fluorocarbene complexes undergo rearrangement to liberate free fluorinated alkenes, a process governed by the choice of solvent and anion, representing a new metal-mediated route to fluorinated alkenes from alkynes.

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Publication details

The article was accepted on 07 Nov 2019 and first published on 08 Nov 2019


Article type: Paper
DOI: 10.1039/C9DT04307A
Dalton Trans., 2019, Accepted Manuscript

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    Solvent- and anion-dependent rearrangement of fluorinated carbene ligands provides access to fluorinated alkenes

    L. Hall, L. Milner, S. Hart, A. C. Whitwood, J. M. Lynam and J. M. Slattery, Dalton Trans., 2019, Accepted Manuscript , DOI: 10.1039/C9DT04307A

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