Issue 30, 2006
From the journal:

Chemical Communications

New reactivity and structural insights of alkali-metal-mediated alumination in directed ortho-alumination of a tertiary aromatic amide

Joaquín García-Álvarez,a   David V. Graham,a   Alan R. Kennedy,a   Robert E. Mulvey*a  and  Susan Weatherstonea  

* Corresponding authors

a WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, UK
E-mail: r.e.mulvey@strath.ac.uk
Fax: +44 (0)141 552 0876

Abstract

The first reported sodium alkyl(TMP)aluminate reagent to be synthesised and crystallographically characterised, [TMEDA·Na(µ-TMP)(µ-iBu)Al(iBu)2], reacts as an amido base towards phenylacetylene to form crystalline [(TMEDA)2·Na(µ-CCPh)(µ-iBu)Al(iBu)2]; whereas the congeneric TMEDA-stabilised lithium (TMP)aluminate exhibits dual alkyl/amido basicity in its reaction with N,N-diisopropylbenzamide to form a novel heterobimetallic-heterotrianionic crystalline complex [{PhC([double bond, length as m-dash]O)N(iPr)2}·Li{2-[1-C([double bond, length as m-dash]O)N(iPr)2]C6H4}{Me2NCH2CH2N(Me)CH2}Al(iBu)2], which, in addition to having an ortho-deprotonated benzamide ligand, also contains a methyl-deprotonated TMEDA ligand and a neutral benzamide molecule ligated to lithium.

Graphical abstract: New reactivity and structural insights of alkali-metal-mediated alumination in directed ortho-alumination of a tertiary aromatic amide

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Article information

DOI
https://doi.org/10.1039/B606080C
Article type
Communication
Submitted
28 Apr 2006
Accepted
26 May 2006
First published
19 Jun 2006

Chem. Commun., 2006, 3208-3210

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New reactivity and structural insights of alkali-metal-mediated alumination in directed ortho-alumination of a tertiary aromatic amide

J. García-Álvarez, D. V. Graham, A. R. Kennedy, R. E. Mulvey and S. Weatherstone, Chem. Commun., 2006, 3208 DOI: 10.1039/B606080C

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