Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 14, 2016
Previous Article Next Article

Synthesis and reactivity of fluorenyl-tethered N-heterocyclic stannylenes

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
16 Oct 2015
Accepted
19 Dec 2015
First published
04 Jan 2016

This article is Open Access

Dalton Trans., 2016,45, 6282-6293
Article type
Paper
Author version available

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements