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.
Shieh
Wen-Chung
WC
Chemical and Analytical Development, Novartis Institute for Biomedical Research, East Hanover, New Jersey 07936, USA. wen.shieh@pharma.novartis.com
Dell
Steven
S
Bach
Andrew
A
Repic
Oljan
O
Blacklock
Thomas J
TJ