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Transition-Metal-Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles.

ABSTRACT: A chemoselective C(sp² )-C(sp² ) coupling of sufficiently electron-deficient fluorinated arenes and functionalized N-aryl-N'-silyldiazenes as masked aryl nucleophiles is reported. The fluoride-promoted transformation involves the in situ generation of the aryl nucleophile decorated with various sensitive functional groups followed by a stepwise nucleophilic aromatic substitution (S_N Ar). These reactions typically proceed at room temperature within minutes. This catalytic process allows for the functionalization of both coupling partners, furnishing highly fluorinated biaryls in good yields.

SUBMITTER: Finck L

PROVIDER: S-EPMC8453572 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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Transition-Metal-Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles.

Finck Lucie L Oestreich Martin M

Chemistry (Weinheim an der Bergstrasse, Germany) 20210610 43

A chemoselective C(sp2 )-C(sp2 ) coupling of sufficiently electron-deficient fluorinated arenes and functionalized N-aryl-N'-silyldiazenes as masked aryl nucleophiles is reported. The fluoride-promoted transformation involves the in situ generation of the aryl nucleophile decorated with various sensitive functional groups followed by a stepwise nucleophilic aromatic substitution (SN Ar). These reactions typically proceed at room temperature within minutes. This c ...[more]

PMID: 34014007

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