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Methylation using dimethylcarbonate catalysed by ionic liquids under continuous flow conditions / Toma N. Glasnov, John D. Holbrey, C. Oliver Kappe, Kenneth R. Seddon and Ting Yan
Verfasser/ VerfasserinKappe, Christian Oliver In der Gemeinsamen Normdatei der DNB nachschlagen ; Glasnov, Toma ; Holbrey, John D. ; Seddon, Kenneth R. ; Yan, Ting
Erschienen in
Green Chemistry, 2012, Jg. 14, H. 12, S. 3071-3076
ErschienenRoyal Society of Chemistry
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SpracheEnglisch
DokumenttypAufsatz in einer Zeitschrift
ISSN1463-9270
URNurn:nbn:at:at-ubg:3-1550 Persistent Identifier (URN)
DOI10.1039/c2gc36226k 
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Methylation using dimethylcarbonate catalysed by ionic liquids under continuous flow conditions [0.38 mb]
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The ionic liquid, tributylmethylammonium methylcarbonate, has been employed as a catalytic base for clean N-methylation of indole with dimethylcarbonate. The reaction conditions were optimised under microwave heating to give 100% conversion and 100% selectivity to N-methylindole, and subsequently transferred to a high temperature/high pressure (285 C/150 bar) continuous flow process using a short (3 min) residence time and 2 mol% of the catalyst to efficiently methylate a variety of different amines, phenols, thiophenols and carboxylic acid substrates. The extremely short residence times, versatility, and high selectivity have significant implications for the synthesis of a wide range of pharmaceutical intermediates, as high product throughputs can be obtained via this scalable continuous flow protocol. It has also been shown that the ionic liquid can be generated in situ from tributylamine, which has the net effect of transforming an ineffective stoichiometric base into a highly efficient catalyst for this broad class of reactions.

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