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Updated: May 21, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Modular Access to Fluorinated Quaternary Stereocenters via Palladium/Lewis Base Synergistic Catalysis
Rixin Liu1, Qinglong Zhang1, Zitong Lin1
1State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin, 300071, China.
Abstract:
The stereocontrolled construction of fluorinated quaternary stereocenters in acyclic systems remains a significant synthetic challenge. We report a synergistic palladium/Lewis base catalytic platform that directly couples α-fluoro-α-aryl acetates with allenes or 1,3-dienes without directing groups. This strategy overcomes traditional limitations in fluoronucleophile activation and stereochemical control, enabling access to diverse acyclic fluorinated architectures. Key to success is the use of axial-chiral Lewis bases, which work cooperatively with palladium catalysts to govern both enantioselectivity and diastereoselectivity. The method accommodates broad substrate scope, including aromatic, heterocyclic, and aliphatic systems, while demonstrating scalability and synthetic versatility through downstream transformations. This work not only bridges essential voids in fluorinated stereochemical space but also enhances the practical applications of synergistic catalyst systems.
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