Premium
Atom Efficient Magnesiation of N ‐Substituted Alkyl Indoles with a Mixed Sodium‐Magnesium Base
Author(s) -
Stevens Michael A.,
Blair Victoria L.
Publication year - 2018
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201701317
Subject(s) - chemistry , deprotonation , steric effects , alkyl , magnesium , medicinal chemistry , reactivity (psychology) , tetramethylethylenediamine , base (topology) , alkylation , metal , molecule , stereochemistry , crystal structure , crystallography , organic chemistry , catalysis , ion , medicine , mathematical analysis , alternative medicine , mathematics , pathology
This study presents the alkali metal mediated magnesiation (AMM Mg ) of three N ‐alkylated indoles with the mixed Na/Mg base [(TMEDA)Na(TMP) 2 Mg(CH 2 SiMe 3 )] 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) 2 Mg(α‐C 9 H 8 N) 4 ] 2 and [(Na‐TMEDA) 2 Mg(α‐C 10 H 11 N) 4 ] 3 , or [(TMEDA)Na(TMP)(α‐C 11 H 12 N)Mg(TMP)] 4 , whereby only one indole molecule is selectively deprotonated.