4.8 Article

Nickel-Catalyzed, Reductive C(sp3)-Si Cross-Coupling of α-Cyano Alkyl Electrophiles and Chlorosilanes

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 34, Pages 18587-18590

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202107492

Keywords

cross-coupling; nickel; silicon; synthetic methods; zinc

Funding

  1. China Scholarship Council
  2. Projekt DEAL
  3. Einstein Foundation Berlin

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A new nickel/zinc-catalyzed cross-electrophile coupling reaction has been reported, utilizing alkyl electrophiles activated by an alpha-cyano group and chlorosilanes. Elemental zinc serves as the stoichiometric reductant in this reductive coupling process, allowing for the formation of a C(sp(3))-Si bond starting from two electrophilic reactants. This method differs from previous approaches that rely on the combination of carbon nucleophiles and silicon electrophiles.
A nickel/zinc-catalyzed cross-electrophile coupling of alkyl electrophiles activated by an alpha-cyano group and chlorosilanes is reported. Elemental zinc is the stoichiometric reductant in this reductive coupling process. By this, a C(sp(3))-Si bond can be formed starting from two electrophilic reactants whereas previous methods rely on the combination of carbon nucleophiles and silicon electrophiles or vice versa.

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