Synthesis and reactivity of an aluminium n-heterocyclic aminal

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Wilde, Taylor and Murphy, Fáinché and Smylie, Cooper R. T. and Kennedy, Alan R. and Weetman, Catherine E. (2024) Synthesis and reactivity of an aluminium n-heterocyclic aminal. Chemistry - An Asian Journal, 19 (5). e202301058. ISSN 1861-471X (https://doi.org/10.1002/asia.202301058)

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Abstract

Tethered N-heterocyclic carbenes (NHCs) are an emerging class of ligand, as they feature all the desirable aspects of NHCs (ease of synthesis, high tunabilty) but also enable metal-ligand cooperativity when combined with Lewis acidic metal centres due to the donor-acceptor nature of the complexes formed. Herein we report a simple ethoxy-tethered NHC for the stabilisation of Al(III) hydrides, resulting in the unexpected formation of a bicyclic N-heterocyclic aminal (1). Compound 1 behaves as a metal hydride, capable of reducing benzophenone and carbodiimide to yield compounds 2 and 3, respectively. Furthermore, we show that 1 behaves as an efficient catalyst in the dehydrocoupling of amine-boranes due to the hemilabile nature of the supporting ligand.

ORCID iDs

Wilde, Taylor, Murphy, Fáinché, Smylie, Cooper R. T., Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Weetman, Catherine E. ORCID logoORCID: https://orcid.org/0000-0001-5643-9256;
  • Item type:Article
    ID code:88211
    Dates:
    Date
    Event
    1 March 2024
    Published
    27 December 2023
    Published Online
    25 December 2023
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:19 Feb 2024 12:17
    Last modified:12 Feb 2025 02:25
    URI:https://strathprints.strath.ac.uk/id/eprint/88211
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