Transition‐Metal‐Free Catalytic Hydrodefluorination of Polyfluoroarenes by Concerted Nucleophilic Aromatic Substitution with a Hydrosilicate | Zendy

Kikushima Kotaro | Zendy; Grellier Mary | Zendy; Ohashi Masato | Zendy; Ogoshi Sensuke | Zendy

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Transition‐Metal‐Free Catalytic Hydrodefluorination of Polyfluoroarenes by Concerted Nucleophilic Aromatic Substitution with a Hydrosilicate

Author(s) -

Kikushima Kotaro,

Grellier Mary,

Ohashi Masato,

Ogoshi Sensuke

Publication year - 2017

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201708003

Subject(s) - chemistry , nucleophilic aromatic substitution , catalysis , nucleophilic substitution , photochemistry , nucleophile , fluoride , hydride , transition metal , medicinal chemistry , inorganic chemistry , metal , organic chemistry

A transition‐metal‐free catalytic hydrodefluorination (HDF) reaction of polyfluoroarenes is described. The reaction involves direct hydride transfer from a hydrosilicate as the key intermediate, which is generated from a hydrosilane and a fluoride salt. The eliminated fluoride regenerates the hydrosilicate to complete the catalytic cycle. Dispersion‐corrected DFT calculations indicated that the HDF reaction proceeds through a concerted nucleophilic aromatic substitution (CS N Ar) process.

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