4.8 Article

Phosphinylation of Non-activated Aryl Fluorides through Nucleophilic Aromatic Substitution at the Boundary of Concerted and Stepwise Mechanisms

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

  1. JSPS KAKENHI [JP18H03906, JP15H05801, JP17H04877, JP20H04793]
  2. Naito Foundation
  3. Ministry of Education, Culture, Sports, Science and Technology through the Hokkaido University Ambitious Leader's Program

向作者/读者索取更多资源

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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