Efficient Allylation of Dihalides: A Versatile Approach to C/N/O-Functionalized Derivatives

Abstract

This study presents an efficient and innovative allylation strategy utilizing C/N/O nucleophilic reagents with attenuated reactivity, enabling the construction of versatile allyl compounds. The approach focuses on the sequential allylation of dihalides in large-scale chemical manufacturing, effectively addressing the challenge of achieving selectivity in cascade reactions. The methodology is centered on the Cu-catalyzed C-olefination of alkynes with dihalides, significantly expediting the synthesis of a diverse array of finely conjugated enyne derivatives. Furthermore, a base-facilitated sequential condensation process has been developed to achieve the N-allylation of hydrazines, yielding a wide range of trisubstituted alkenyl hydrazones. Additionally, the protocol enables the synthesis of high-value ester compounds through O-allylation or esterification with dihalides. This transformation also facilitates the one-step synthesis of a variety of essential pharmaceuticals, demonstrating its broad synthetic utility and potential.

Keywords

Dihalides / Esters / Enynes / Alkenyl hydrazones / Allylation

RIGHTS & PERMISSIONS

2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH