Phospha-Michael Addition on α-Fluorinated Acrylates: A Straightforward Access to Polyfunctionalized Fine Chemicals
Xin Huang1, Tatiana Besset1, Philippe Jubault1
1Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France.
Abstract:
α-Fluorinated acrylates could act as Michael acceptors and become a platform toward the synthesis of relevant complex molecules. Very few conjugate additions have been developed in the literature with these specific substrates, and herein, we reported the first phospha-Michael addition (PMA) on α-trifluoromethylacrylates and α-fluoromethylacrylates. The reaction proved to be highly tolerant and gave original products containing contiguous C-P and C-CFY2 (Y = F or H) bonds in good to excellent yields and diastereoselectivities.
More Related Videos
Related Concept Videos
Conjugate Addition of Enolates: Michael Addition
Anionic Chain-Growth Polymerization: Overview
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...


