Ligand-Controlled Preparation of Aryl-Substituted Allenes Enabled by Nickel-Catalyzed Reductive Coupling of Secondary Propargylic Carbonates with Aryl Halides

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 15, 2025

Herein, we developed a new method for the synthesis of aryl-substituted allenes through nickel-catalyzed reductive coupling reaction between secondary propargyl carbonates and aryl halides. By employing dimethyl-1,10-phenanthroline ligand, achieved ligand-controlled, regioselective arylation, overcoming structural limitations electrophiles. Notably, this exhibits exceptional functional group compatibility, rendering it particularly suitable late-stage allenylation modifications complex molecules.

Language: Английский

Nickel-Catalyzed Photoredox Allenylation of Alkyl Halides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(44), P. 9519 - 9524

Published: Oct. 25, 2024

We report a dual Ni/photoredox-catalyzed cross-coupling method for propargyl carbonates and nonactivated alkyl bromides, facilitating the synthesis of variety substituted allenes under mild practical conditions. Mechanistically, reaction integrates Ni-catalyzed activation electrophile via SN2′ oxidative addition at Ni(I) with silyl radical-induced halide through halogen-atom transfer. This methodology provides gentle approach introducing allenyl groups into complex halogenated aliphatic molecules, offering further opportunities derivatization.

Language: Английский