4.8 Article

Geminal Silicon/Zinc Reagent as an Equivalent of Difluoromethylene Bis-carbanion

Journal

ORGANIC LETTERS
Volume 16, Issue 5, Pages 1438-1441

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol5002297

Keywords

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Funding

  1. Ministry of Science [MD-1151.2011.3]
  2. Russian Foundation for Basic Research [13-03-12074, 14-03-00293, 14-03-31253_mol_a, 14-03-31265_mol_a]
  3. Russian Academy of Sciences

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A new difluorinated reagent, [difluoro(trimethylsilyl)methyl]zinc bromide, bearing C-Zn and C-Si bonds is described. The reagent is conveniently prepared by cobalt-catalyzed halogen/zinc exchange. It can be coupled with two different C-electrophiles in a stepwise manner (with allylic halides for C-Zn bond and aldehydes for C-Si bond) affording products containing a difluoromethylene fragment.

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