Copper-Catalyzed Cascade Coupling/Cyclization/Switchable aza-Claisen Rearrangement for Indole Skeletons
Abstract
A copper-catalyzed cascade coupling/cyclization/switchable aza-Claisen rearrangement was disclosed for the first time, realizing the divergent synthesis of 2,3-disubstituted, C3-allylated, or C2-but-3-en-1-ylated indole derivatives from N -allyl-2 alkynylanilines and diazo compounds. Compared to previous works, the application of diazo compounds as coupling partners significantly expanded the variety of functional groups on the C2 position. Importantly, a catalytic amount of organic base, triethylamine, was found to act as a chemical switch to govern two different aza-Claisen rearrangement pathways.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Catalytic Alkyne Reactions
Catalytic Cross-Coupling Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 17
- Pages
- 5502–5507
- Publication date
- 21 April 2026
- Language
- EN