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Issue 14, 2016
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Synthesis and reactivity of fluorenyl-tethered N-heterocyclic stannylenes

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Abstract

A fluorenyl (Fl) tethered diamine was synthesised by nucleophilic substitution of (bromoethyl)fluorene with a diisopropylphenyl (Dipp) substituted diamine to give FlC2H4N(H)C2H4N(H)Dipp (1a) in good yield (85%). Lithiation of 1a with n-BuLi proceeded with coordination of the Li cation to the aromatic fluorenide ring (2), and with subsequent equivalents of n-BuLi, the secondary amines were then sequentially deprotonated. A fluorenyl-tethered N-heterocyclic stannylene (NHSn) was synthesised from the reaction of 1a with SnN′′2 {N′′ = N(SiMe3)2} as a neutral dimeric species (5), and this was deprotonated with LiN′′ to give the corresponding dianionic fluorenide-tethered NHSn (6). Reactions of [{Rh(cod)(μ-Cl)}2] with the mono-deprotonated ligand 2 led to the formation of a mixed-donor amide–amine Rh(I) compound (7), whereas reactions with the anionic NHSn 6 led to a Rh–fluorenyl complex of low stability with an uncoordinated pendent NHSn arm, which X-ray crystallography showed to be dimeric in the solid state.

Graphical abstract: Synthesis and reactivity of fluorenyl-tethered N-heterocyclic stannylenes

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Publication details

The article was received on 16 Oct 2015, accepted on 19 Dec 2015 and first published on 04 Jan 2016


Article type: Paper
DOI: 10.1039/C5DT04060D
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Citation: Dalton Trans., 2016,45, 6282-6293
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    Synthesis and reactivity of fluorenyl-tethered N-heterocyclic stannylenes

    M. Roselló-Merino and S. M. Mansell, Dalton Trans., 2016, 45, 6282
    DOI: 10.1039/C5DT04060D

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