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Shieh, W.C. et al.

Shieh, Dell, Bach, Repic, Blacklock,

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 involves 1,4-diazabicyclo[2.2.2]octane (DABCO) dually as a nucleophilic catalyst, ultimately resulting in a single product: the N-methylated indole.[1]

References

Dual nucleophilic catalysis with DABCO for the N-methylation of indoles. Shieh, W.C., Dell, S., Bach, A., Repic, O., Blacklock, T.J. J. Org. Chem. (2003) [Pubmed]

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