TriMethyl(broModifluoroMethyl)silane

Uses

Novel difluorocarbene source for the efficient difluoromethylenation of alkenes/alkynes and difluoromethylation of O-, S-, and N-nucleophiles.

Uses

Trimethyl(bromodifluoromethyl)silane can be used as neuroactive steroids.

Uses

As reported by Hu and co-workers, (Bromodifluoromethyl)trimethylsilane is a highly useful reagent for the formation of difluoromethene-containing 3-membered rings and can also difluoromethylate heteroatoms with the assistance of alkaline bases, most effectively KOH.

Reactions

(1) Difluoromethylenation of TMSCN.

Ref. J. Org. Chem. 2012, 77, 5850?5855.
(2) Difluoromethylenation of benzyl and alkylzinc halides.

Ref. Org. Lett. 2013, 15, 917 – 919.
(3) Fluorination aminocarbonylation of aldehydes

Ref. Angew. Chem. Int. Ed. 2022, e202115467

General Description

(Bromodifluoromethyl)trimethylsilane (TMSCF₂Br) is commonly used as a source to generate dilfluorocarbene. TMSCF₃ (Ruppert–Prakash reagent) and BBr₃ undergoes fast halogen–exchange reaction to form MSCF₂Br.

References

[1]Angewandte Chemie International Edition.DOI :10.1002/anie.202283811
[2]The Journal of Organic Chemistry.DOI :10.1021/acs.orglett.2c02899