Synthesis and reactivity of an aluminium n-heterocyclic aminal

Taylor Wilde; Fáinché Murphy; Cooper R. T. Smylie; Alan R. Kennedy; Catherine E. Weetman

doi:10.1002/asia.202301058

Synthesis and reactivity of an aluminium n-heterocyclic aminal

Taylor Wilde, Fáinché Murphy, Cooper R. T. Smylie, Alan R. Kennedy, Catherine E. Weetman

Pure And Applied Chemistry

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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.

Original language	English
Article number	e202301058
Number of pages	5
Journal	Chemistry - An Asian Journal
Volume	19
Issue number	5
Early online date	27 Dec 2023
DOIs	https://doi.org/10.1002/asia.202301058
Publication status	Published - 1 Mar 2024

Keywords

aluminium
main group hydrides
ligand design
N-heterocyclic carbenes

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10.1002/asia.202301058Licence: CC BY 4.0

Wilde-etal-CAAJ-2023-Synthesis-and-reactivity-of-an-aluminium-n-heterocyclic-aminalFinal published version, 2.09 MBLicence: CC BY 4.0

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Data For "Synthesis and Reactivity of an Aluminium N-heterocyclic Aminal"
Weetman, C. (Creator), Kennedy, A. (Contributor), Murphy, F. (Contributor), Smylie, C. (Contributor) & Wilde, T. (Contributor), University of Strathclyde, 22 Apr 2024
DOI: 10.15129/22b66cde-d7b9-48a8-8e5b-af26a0581730
Dataset

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title = "Synthesis and reactivity of an aluminium n-heterocyclic aminal",

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.",

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T1 - Synthesis and reactivity of an aluminium n-heterocyclic aminal

AU - Wilde, Taylor

AU - Murphy, Fáinché

AU - Smylie, Cooper R. T.

AU - Kennedy, Alan R.

AU - Weetman, Catherine E.

PY - 2024/3/1

Y1 - 2024/3/1

N2 - 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.

AB - 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.

KW - aluminium

KW - main group hydrides

KW - ligand design

KW - N-heterocyclic carbenes

U2 - 10.1002/asia.202301058

DO - 10.1002/asia.202301058

M3 - Article

SN - 1861-4728

VL - 19

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

IS - 5

M1 - e202301058

ER -

Synthesis and reactivity of an aluminium n-heterocyclic aminal

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Data For "Synthesis and Reactivity of an Aluminium N-heterocyclic Aminal"

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