Redox‐Neutral Copper(II) Carboxylate Catalyzed α‐Alkynylation of Amines

2013/02/25 by Deepankar Das, Aaron X. Sun, Daniel Seidel · 4 citations
Chemistry · #Catalytic Alkyne Reactions #Catalytic Cross-Coupling Reactions #Catalytic C–H Functionalization Methods

paper · doi:10.1002/anie.201300021

openalex publication_date 2013/02/25 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

Cocktail of three: A new strategy for iminium ion isomerization was applied to the direct, redox-neutral α-alkynylation of amines. Copper(II) 2-ethylhexanoate [Cu(2-EH)2] was identified as the optimal catalyst for this three-component coupling reaction of secondary amines, aldehydes, and alkynes. MW=microwave.

Citations

• A walk around the A3-coupling
• Synergistic catalysis: A powerful synthetic strategy for new reaction development
• Base-Catalyzed, Three-Component Coupling of Aldehydes, Terminal Aryl Acetylenes, and Amines: Application to Synthesis of Propargylamines
• Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp3−Csp) of Natural α-Amino Acids and Alkynes
• Nontraditional Reactions of Azomethine Ylides: Decarboxylative Three-Component Couplings of α-Amino Acids
• Highly efficient Grignard-type imine additions via C–H activation in water and under solvent-free conditions

Cited by

• The redox-A 3 reaction
• CuI-Catalyzed C1-Alkynylation of Tetrahydroisoquinolines (THIQs) by A3 Reaction with Tunable Iminium Ions
• Highly stable polyoxometalate-based CuI–MOFs for multisite synergistic catalysis of the A3 coupling reaction
• A3 coupling reaction [wikipedia]