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

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JournalDalton transactions (Cambridge, England : 2003)
DateAccepted/In press - 7 Nov 2019
DateE-pub ahead of print (current) - 8 Nov 2019
Issue number47
Number of pages5
Pages (from-to)17655-17659
Early online date8/11/19
Original languageEnglish


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)([double bond, length as m-dash]C[double bond, length as m-dash]CPhF)][N(SO2Ph)2] with [NMe4]F results in nucleophilic attack of fluoride at the metal-bound carbon of the vinylidene ligand to give alkenyl complex [Ru(η5-C5H5)(dppe)(-CF[double bond, length as m-dash]CFPh)]. Subsequent eletrophilic fluorination with N-fluorobenzenesulfonimide (NFSI) results in the formation of the fluorinated carbene complex [Ru(η5-C5H5)(dppe)([double bond, length as m-dash]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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