Palladium-catalyzed regio- and enantio-selective trifluoromethylated allylic alkylation of diphenylphosphine oxides

Abstract

The first convenient method for the allylic alkylation of diphenylphosphine oxides catalyzed by palladium has been designed and developed, affording various chiral allylphosphine oxides bearing CF3 groups with exclusive regio-selectivity and excellent enantioselective control. The reaction was performed in one pot under relatively mild reaction conditions using “easy-to-prepare” starting materials and relatively inexpensive chiral bis(phosphines) ligands. Further transformations of a representative product confirm the feasibility and potential applications of our synthetic strategies. In conclusion, this study provides a valuable method method for synthesizing chiral molecules bearing CF3 and allylphosphine oxide.

Graphical abstract: Palladium-catalyzed regio- and enantio-selective trifluoromethylated allylic alkylation of diphenylphosphine oxides

Supplementary files

Article information

Article type
Paper
Submitted
20 Jan 2025
Accepted
29 Mar 2025
First published
31 Mar 2025

Org. Biomol. Chem., 2025, Advance Article

Palladium-catalyzed regio- and enantio-selective trifluoromethylated allylic alkylation of diphenylphosphine oxides

S. Zhang, Y. Liu, L. Sun, B. Wang, J. Zhao, J. Qu and Y. Zhou, Org. Biomol. Chem., 2025, Advance Article , DOI: 10.1039/D5OB00096C

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