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

You Zhensheng | Zendy; Higashida Kosuke | Zendy; Iwai Tomohiro | Zendy; Sawamura Masaya | Zendy

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

Author(s) -

You Zhensheng,

Higashida Kosuke,

Iwai Tomohiro,

Sawamura Masaya

Publication year - 2021

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.202013544

Subject(s) - chemistry , nucleophile , aryl , concerted reaction , medicinal chemistry , nucleophilic substitution , phosphine , nucleophilic aromatic substitution , substitution reaction , reaction mechanism , radical nucleophilic aromatic substitution , photochemistry , organic chemistry , catalysis , alkyl

Non‐activated aryl fluorides reacted with potassium diorganophosphinites through a nucleophilic aromatic substitution (S N Ar) 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 S N Ar reaction pathways.

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