| Identification | Back Directory | [Name]
Fluorobis(phenylsulfonyl)methane | [CAS]
910650-82-7 | [Synonyms]
Fluorobis(phenylsulfonyl)methane
Bis(phenylsulfonyl)fluoromethane
(Fluoromethylenedisulfonyl)dibenzene
1,1'-[(Fluoromethylene)bis(sulfonyl)]bis-benzene
Benzene, 1,1'-[(fluoromethylene)bis(sulfonyl)]bis- | [Molecular Formula]
C13H11FO4S2 | [MDL Number]
MFCD11036372 | [MOL File]
910650-82-7.mol | [Molecular Weight]
314.35 |
| Hazard Information | Back Directory | [Description]
Fluorobis(phenylsulfonyl)methane (FBSM), can be deprotonated under much milder basic
conditions than those required for the deprotonation of fluoromethyl phenyl sulfone, and thus has
been used as an excellent nucleophilic fluoromethylation reagent in many catalytic asymmetric
reactions with allyl esters, imines, and α,β-unsaturated compounds. Stereoselctive nucleophilic
substitution reaction between chiral alcohols and FBSM under Mitsunobu conditions gives the
fluoromethylated products with full inversion of the configuration. Nucleophilic substitution
reaction of epoxides and aziridines with FBSM gives the precursors of β-fluoromethylated
alcohols and amines in high yields. As a carbon acid, FBSM can also be used in cross
dehydrogenative coupling reaction. | [Uses]
(Fluoromethylenedisulfonyl)dibenzene is a nucleophilic fluoromethylating agent. | [Reactions]
(1) Monofluoromethylation of allyl esters.
(2) Monofluoromethylation of Morita–Baylis–Hillman carbonates.
(3) Monofluoromethylation of imines.
(4) Monofluoromethylation of α,β-unsaturated ketones and aldehydes.
(5) Monofluoromethylation of α,β-unsaturated ketones and aldehydes.
(6) Monofluoromethylation of epoxides.
(7) Monofluoromethylation of aldehydes.
(8) Monofluoromethylation of tertiary amines.
 | [References]
[1] HYOUNG WOOK MOON; Dae Y K; Min Je Cho. Enantioselective conjugate addition of fluorobis(phenylsulfonyl)methane to α,β-unsaturated ketones catalyzed by chiral bifunctional organocatalysts[J]. Tetrahedron Letters, 2009. DOI:10.1016/j.tetlet.2009.06.056.
[2] XIAOMING ZHAO. ChemInform Abstract: Highly Regioselective Pd-Catalyzed Allylic Alkylation of Fluorobis(phenylsulfonyl)methane[J]. ChemInform, 2011. DOI:10.1002/chin.201118076.
[3] G. K. SURYA PRAKASH. Efficient Nucleophilic Fluoromethylation and Subsequent Transformation of Alkyl and Benzyl Halides Using Fluorobis(phenylsulfonyl)methane[J]. Organic Letters, 2009. DOI:10.1021/ol8029627.
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