Dual Nucleophilic Catalysis with DABCO for the N-Methylation of Indoles

Dual Nucleophilic Catalysis with DABCO for the N-Methylation of Indoles

DABCO is an extremely active catalyst for the methylation of indoles in conjunction with dimethyl carbonate (DMC). This green chemistry is highly effective and produces N-methylindoles in nearly quantitative yields. The reaction sequence consists of competing alkylation and acylation pathways and in...

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Veröffentlicht in:Journal of organic chemistry 2003-03, Vol.68 (5), p.1954-1957
Hauptverfasser: Shieh, Wen-Chung, Dell, Steven, Bach, Andrew, Repič, Oljan, Blacklock, Thomas J
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Zusammenfassung:DABCO is an extremely active catalyst for the methylation of indoles in conjunction with dimethyl carbonate (DMC). This green chemistry is highly effective and produces N-methylindoles in nearly quantitative yields. The reaction sequence consists of competing alkylation and acylation pathways and involves 1,4-diazabicyclo[2.2.2]octane (DABCO) dually as a nucleophilic catalyst, ultimately resulting in a single product:  the N-methylated indole.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0266644