Phosphinylation of Non‐activated Aryl Fluorides through Nucleophilic Aromatic Substitution at the Boundary of Concerted and Stepwise Mechanisms
Authors:
- 2 December 2020
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 60 (11) , 5778-5782
Abstract
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.Keywords
Funding Information
- Japan Society for the Promotion of Science (17H04877, JP20H04793, JP18H03906, JP15H05801)
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