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Issue 31, 2018
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On the alcoholysis of alkyl-aluminum(iii) alkoxy-NHC derivatives: reactivity of the Al-carbene Lewis pair versus Al-alkyl

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Abstract

The reaction of a bifunctional hydroxy N-heterocyclic carbene (NHC-OH) ligand with alkyl-aluminum(III) derivatives appears to be dependent on the precursor used. The expected alkoxy-NHC metallated product is indeed obtained with Al(iBu)3. In contrast, the sterically hindered [Al(iBu)(OAr)2] (OAr = 2,6-di-tert-butyl-4-methylphenoxy) displays reactivity at the carbene and affords an imidazolium-aluminate zwitterion. The non-innocence of the Al–NHC motif is further highlighted by the heterolytic cleavage of the phenol O–H bond across the Al–CNHC bond from Al(O-NHC)X2 derivatives (X = iBu, OAr).

Graphical abstract: On the alcoholysis of alkyl-aluminum(iii) alkoxy-NHC derivatives: reactivity of the Al-carbene Lewis pair versus Al-alkyl

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Article information


Submitted
16 Apr 2018
Accepted
29 Jun 2018
First published
05 Jul 2018

Dalton Trans., 2018,47, 10429-10433
Article type
Communication

On the alcoholysis of alkyl-aluminum(III) alkoxy-NHC derivatives: reactivity of the Al-carbene Lewis pair versus Al-alkyl

V. Dardun, L. Escomel, E. Jeanneau and C. Camp, Dalton Trans., 2018, 47, 10429
DOI: 10.1039/C8DT01498A

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