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

Citations Over TimeTop 16% of 2003 papers

Abstract

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.

Related Papers

• → A facile synthesis of highly functionalized dihydrofurans based on 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed reaction of halides with enones(2005)73 cited
• → 1,4-Diazabicyclo[2.2.2]octane (DABCO) as a useful catalyst in organic synthesis(2010)71 cited
• → Organic reactions catalyzed by 1, 4-diazabicyclo [2.2.2] octane (DABCO)(2008)30 cited
• → Unveiling the mechanism of N‐methylation of indole with dimethylcarbonate using either DABCO or DBU as catalyst(2021)4 cited
• → Synthesis of perdeuterio‐1,4‐diazabicyclo[2,2,2]octane (DABCO‐2H₁₂)(1988)1 cited