CuI-Catalyzed C1-Alkynylation of Tetrahydroisoquinolines (THIQs) by A3 Reaction with Tunable Iminium Ions

2013/11/15 by Qinheng Zheng, Wei Meng, Guo-Jie Jiang +1 · 2 citations
Chemistry · #Catalytic Alkyne Reactions #Catalytic Cross-Coupling Reactions #Catalytic C–H Functionalization Methods

paper · doi:10.1021/ol402517e

openalex publication_date 2013/11/15 · openalex created_date 2016/06/24 · openalex updated_date 2026/07/30

Abstract

A CuI-catalyzed A(3) (amines, aldehydes and alkynes) reaction of tetrahydroisoquinolines (THIQs), aldehydes, and alkynes to give C1-alkynylated THIQ products (endo-yne-THIQs) was developed. This redox neutral C1-alkynylation of THIQs, which was conducted under mild conditions, has a broad scope for the used aldehydes and alkynes. It was proposed that the A(3) reaction first generates in situ exo-iminium ions, which then isomerize to endo-iminium ions and react with copper acetylides to give the endo alkynylated THIQs (endo-yne-THIQs).

Citations

• A walk around the A3-coupling
• Nontraditional Reactions of Azomethine Ylides: Decarboxylative Three-Component Couplings of α-Amino Acids
• Redox‐Neutral Copper(II) Carboxylate Catalyzed α‐Alkynylation of Amines

Cited by

• The redox-A 3 reaction
• A3 coupling reaction [wikipedia]