Abstract
This study presents the alkali metal mediated magnesiation (AMMMg) of three N-alkylated indoles with the mixed Na/Mg base [(TMEDA)Na(TMP)2Mg(CH2SiMe3)] 1 (TMEDA = N,N,N′,N′-tetramethylethylenediamine, TMP = 2,2,6,6-tetramethylpiperidine). All three magnesiated indoles have been successfully characterised by single-crystal X-ray diffraction and solution state NMR studies, whereas iodolysis and Pd-catalysed cross coupling have been investigated. The steric nature of the N-alkyl group changes the reactivity and efficiency of 1 to give either atom efficient disodium tetraindol-2-ylmagnesiates [(Na-TMEDA)2Mg(α-C9H8N)4] 2 and [(Na-TMEDA)2Mg(α-C10H11N)4] 3, or [(TMEDA)Na(TMP)(α-C11H12N)Mg(TMP)] 4, whereby only one indole molecule is selectively deprotonated.
Original language | English |
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Pages (from-to) | 74-79 |
Number of pages | 6 |
Journal | European Journal of Inorganic Chemistry |
Volume | 2018 |
Issue number | 1 |
DOIs | |
Publication status | Published - 10 Jan 2018 |
Externally published | Yes |