Phosphinylation of Non‐activated Aryl Fluorides through Nucleophilic Aromatic Substitution at the Boundary of Concerted and Stepwise Mechanisms.
- Resource Type
- Article
- Authors
- You, Zhensheng; Higashida, Kosuke; Iwai, Tomohiro; Sawamura, Masaya
- Source
- Angewandte Chemie International Edition. 3/8/2021, Vol. 60 Issue 11, p5778-5782. 5p.
- Subject
- *FLUORIDES
*PHOSPHINE oxides
*POTASSIUM fluoride
*PHOSPHINES
*NUCLEOPHILES
- Language
- ISSN
- 1433-7851
Non‐activated aryl fluorides reacted with potassium diorganophosphinites through a nucleophilic aromatic substitution (SNAr) reaction. Remarkably, both electron‐neutral and electron‐rich aryl fluorides participated in the reaction with substantially stabilized anionic P nucleophiles to form the corresponding tertiary phosphine oxides. Quantum chemical calculations suggested a nucleophile‐dependent mechanism that involves both concerted and stepwise SNAr reaction pathways. [ABSTRACT FROM AUTHOR]