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Practical Tetrafluoroethylene Fragment Installation Through a Coupling Reaction of (1,1,2,2-tetrafluorobut-3-en-1-yl)zinc Bromide With Various Electrophiles

Practical Tetrafluoroethylene Fragment Installation Through a Coupling Reaction of (1,1,2,2-tetrafluorobut-3-en-1-yl)zinc Bromide With Various Electrophiles

Ken Tamamoto, Shigeyuki Yamada, Tsutomu Konno

Beilstein J Org Chem. 2018 Sep 11;14:2375-2383.

PMID: 30254702

Abstract:

(1,1,2,2-Tetrafluorobut-3-en-1-yl)zinc bromide was prepared by insertion of the zinc-silver couple into the CF2-Br bond of commercially available 4-bromo-3,3,4,4-tetrafluorobut-1-ene in DMF at 0 °C for 0.5 h, The resultant polyfluorinated zinc reagent was found to be thermally stable at ambient temperature and storable for at least 1.5 years in the refrigerator. This CF2CF2-containing organozinc reagent could be easily transmetallated to copper species, which underwent cross-coupling reactions with various aromatic iodides or acyl chlorides to produce a broad range of CF2CF2-containing organic molecules in good-to-excellent yields. Therefore, the zinc reagent could become a new and practical synthetic tool for producing functional molecules with a CF2CF2 fragment.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP7699458	Zinc bromide		7699-45-8	Price

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