期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 11, 页码 5778-5782出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202013544
关键词
aryl fluorides; nucleophilic substitution; phosphinylation; reaction mechanisms; tertiary phosphine oxides
资金
- JSPS KAKENHI [JP18H03906, JP15H05801, JP17H04877, JP20H04793]
- Naito Foundation
- Ministry of Education, Culture, Sports, Science and Technology through the Hokkaido University Ambitious Leader's Program
In this study, non-activated aryl fluorides were found to react with potassium diorganophosphinites through nucleophilic aromatic substitution to form tertiary phosphine oxides, with a mechanism involving nucleophile-dependent SNAr reaction pathways.
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.
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