Direct Synthesis of 2-Alkynylindolin-3-ones via Copper-Catalyzed Reductive Alkynylation of 2-Arylisatogens
Abstract
2-Alkynylindolin-3-ones (pseudoindoxyl derivatives) are accessed directly from 2-arylisatogens through a CuTC-catalyzed reductive alkynylation with terminal alkynes. The transformation proceeds in a one-step cascade, combining alkyne addition at the 2-position of the isatogen nucleus with concurrent N-O bond cleavage to deliver 2-alkynylindolin-3-ones in yields of up to 89% under relatively mild thermal conditions. The method displays a broad substrate scope and operational simplicity, highlighting its value as a practical entry to this class of heterocycles. Control experiments further reveal a redox interplay of copper species, sustained by molecular oxygen, which underpins the tandem alkyne addition and N-O bond reduction events.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Catalytic Alkyne Reactions
Catalytic Cross-Coupling Reactions
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 2
- Pages
- 1188–1197
- Publication date
- 6 January 2026
- Language
- EN