C3-Heteroarylation of Indoles via Cu(II)-Catalyzed Aminocupration and Subsequent Nucleophilic Addition of o-Alkynylanilines

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 23, 2025

Transition-metal-catalyzed aminometalation of o-alkynylanilines is a promising pathway for the synthesis C3-functionalized indoles. Herein, we describe Cu(II)-catalyzed site-selective C3-heteroarylation indoles from and quinoline N-oxides. A plausible reaction mechanism involving aminocupration followed by nucleophilic addition Cu(II)-indolyl complexes to N-oxides was proposed. Post-transformations generated C3-heteroarylated demonstrated broad applicability developed method.

Language: Английский

Synthesis of Quinoline–Indole Hybrids through Cu(II)-Catalyzed Amination and Annulation between N-Oxides and o-Alkynylanilines

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 16, 2024

The synthesis of (iso)quinoline-indole hybrids by reacting (iso)quinoline N-oxides with o-alkynylanilines in the presence a combination copper(II) catalyst and bidentate 2,2′-bipyridine ligand is described. utility this method was demonstrated through site-selective functionalization synthesized products. A plausible reaction pathway for amination followed annulative indole formation elucidated series mechanistic investigations.

Language: Английский