Difluoromethyl phenyl sulfone

Description

Difluoromethyl phenyl sulfone is a powerful nucleophilic difluoromethylation reagent due to the high reactivity of the sulfonyl-stabilized difluoromethyl anion towards many electrophiles including carbonyls, imines, alkyl halides, and cyclic sulfates and sulfamidates. In the nucleophilic reaction step, depending on the substrate structure, strong bases are used to generate the nucleophilic (phenylsulfonyl)difluoromethyl anion in situ. In the desulfonylation step, sodium/mercury amalgam and magnesium are the commonly used reductive reagents. Besides, the (phenylsulfonyl)difluoromethylated compounds can undergo β-elimination to afford gem-difluoroalkenes.

Chemical properties

light yellow liquid

The Uses of Difluoromethyl phenyl sulfone

Difluoromethyl Phenyl Sulfone has been used as a reagent for the nucleophilic difluoro(phenylsulfonyl)methylation of carbonyls

The Uses of Difluoromethyl phenyl sulfone

Efficient reagent for difluoromethylation of carbonyls and aldehydes.

What are the applications of Application

Difluoromethyl phenyl sulfone is a synthesis reagent that may be used for fluorination

Reactions

(1) Difluoromethylation of alkyl halides.

(2) Difluoromethylation of aldehydes and ketones.

(3) Difluoromethylenation of aldimines and ketimines.

(4) Difluoromethylation of cyclic sulfates and sulfamidates.

(5) (Phenylsulfonyl)difluoromethylation of carboxylic acid esters.

(6) Difluoromethylenation of alkyl halides.

(7) Difluoromethylenation of aromatic aldehydes.

References

[1] G. PRAKASH. Nucleophilic difluoromethylation of primary alkyl halides using difluoromethyl phenyl sulfone as a difluoromethyl anion equivalent.[J]. Organic Letters, 2004. DOI:10.1002/CHIN.200509059.
[2] G. K. SURYA PRAKASH. Difluoromethyl Phenyl Sulfone, a Difluoromethylidene Equivalent: Use in the Synthesis of 1,1-Difluoro-1-alkenes.[J]. ChemInform, 2005. DOI:10.1002/chin.200504098.
[3] G. K. SURYA PRAKASH. Nucleophilic Difluoromethylation of Primary Alkyl Halides Using Difluoromethyl Phenyl Sulfone as a Difluoromethyl Anion Equivalent[J]. Organic Letters, 2004, 6 23: 4315-4317. DOI:10.1021/ol048166i.