A walk around the A3-coupling

2012/01/01 by Vsevolod A. Peshkov, Olga P. Pereshivko, Erik V. Van der Eycken · 6 citations
Chemistry · #Aldehyde #Alkyne #Amine gas treating #Catalysis #Catalytic Alkyne Reactions #Catalytic C–H Functionalization Methods #Chemistry #Click Chemistry and Applications #Combinatorial chemistry #Component (thermodynamics) #Coupling (piping) #Coupling reaction #Materials science #Nanotechnology #Organic chemistry #Physics #Tandem

paper · doi:10.1039/c2cs15356d

openalex publication_date 2012/01/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/05

Abstract

In recent years, the transition-metal catalyzed three-component coupling of an aldehyde, an alkyne and an amine, commonly called A(3)-coupling, has been established as a convenient and general approach towards propargylamines. Furthermore, the A(3)-coupling has found a broad application as a key step in the construction of various nitrogen-containing heterocycles, biologically active compounds and natural products. Several interesting modifications of the A(3)-coupling as well as different tandem reactions involving A(3)-coupling have been developed. This tutorial review aims to highlight the current achievements in the field of A(3)-couplings and related transformations.

Citations

• Aldehyde- and Ketone-Induced Tandem Decarboxylation-Coupling (Csp3−Csp) of Natural α-Amino Acids and Alkynes
• Enantioselective Direct-Addition of Terminal Alkynes to Imines Catalyzed by Copper(I)pybox Complex in Water and in Toluene
• A Highly Efficient Three-Component Coupling of Aldehyde, Alkyne, and Amines via C−H Activation Catalyzed by Gold in Water
• Highly efficient Grignard-type imine additions via C–H activation in water and under solvent-free conditions
• Direct Addition of TMS-acetylene to Aldimines Catalyzed by a Simple, Commercially Available Ir(I) Complex

Cited by

• Enantioselective Double Manipulation of Tetrahydroisoquinolines with Terminal Alkynes and Aldehydes under Copper(I) Catalysis
• Redox‐Neutral Copper(II) Carboxylate Catalyzed α‐Alkynylation of Amines
• 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]

Related

• 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
• Propargyl Claisen rearrangement: allene synthesis and beyond
• Nontraditional Reactions of Azomethine Ylides: Decarboxylative Three-Component Couplings of α-Amino Acids
• A Generalized Picture of C–C Cross-Coupling