Fluorobis(phenylsulfonyl)methane

Synonym
Product Category
Product Code
CAS Number
MDL Number
Pubchem CID
Reaxys RN
(PhSO2)2CHF,FBSM,1-fluoro-1,1-bis(phenylsulfonyl)methane
Fluoromethylating Reagents
KUMI1F09
910650-82-7
 
16079185
10539988
image-155171-Trimethyl(trifluoromethyl)silane_reagent.png
Chemical Name
Molecular Formula
Molecular Weight
Assay(Analysis Method)
Appearance
Melting Point
Packaging
Storage
Fluorobis(phenylsulfonyl)methane
C13H11FO4S2
314.36
≥98.0%(NMR)
White Solid
105-106°C
5g,10g,50g and 100g
Store at room temperature
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.
Fluorobis(phenylsulfonyl)methane: A Fluoromethide Equivalent and Palladium-Catalyzed Enantioselective Allylic Monofluoromethylation.[1]
Nucleophilic fluoroalkylation of epoxides with fluorinated sulfones.[2]
Cinchona alkaloid-catalyzed enantioselective monofluoromethylation reaction based on fluorobis(phenylsulfonyl)methane chemistry combined with a Mannich-type reaction.[3]
Stereoselective monofluoromethylation of primary and secondary alcohols by using a fluorocarbon nucleophile in a Mitsunobu reaction.[4]
Catalytic enantioselective Michael addition of 1-fluoro-bis (phenylsulfonyl)methane to α,β-unsaturated ketones catalyzed by cinchona alkaloids.[5]
Catalytic enantioselective Michael addition of 1-fluoro-bis (phenylsulfonyl)methane to α,β-unsaturated ketones catalyzed by cinchona alkaloids.[5]
Iridium-catalyzed regio- and enantioselective allylic alkylation of fluorobis(phenylsulfonyl)methane.[6]
Formal highly enantioselective organocatalytic addition of fluoromethyl anion to α,β-unsaturated aldehydes.[7]
Enantioselective conjugate addition of fluorobis(phenylsulfonyl)methane to α,β-unsaturated ketones catalyzed by chiral bifunctional organocatalysts.[8]
Asymmetric allylic monofluoromethylation and methylation of morita-baylis-hillman carbonates with FBSM and BSM by cooperative cinchona alkaloid/FeCl2 catalysis.[9]
Nucleophilic fluoromethylation of aldehydes with fluorobis(phenylsulfonyl) methane: The importance of strong Li-O coordination and fluorine substitution for C-C bond formation.[10]
DIAD-mediated metal-free cross dehydrogenative coupling between tertiary amines and α-fluorinated sulfones.[11]
References:
[1] T. Fukuzumi,N. Shibata, M. Sugiura, H.Yasui,S.Nakamura, Angew. Chem. Int. Ed. 2006, 45(30), pp 4973-4977.
[2] C.Ni, Y.Li, J.Hu, J. Org. Chem. 2006, 71(18), pp 6829-6833.
[3] S.Mizuta, N.Shibata, Y.Goto, T.Furukawa, S. Nakamura, T.Toru, J. Am. Chem. Soc., 2007, 129(20), pp 6394-6395.
[4] G.K.S. Prakash, S. Chacko, S. Alconcel, T. Stewart, T. Mathew, G.A.Olah, Angew. Chem. Int. Ed., 2007,46(26),pp 4933-4936.
[5] T. Furukawa, N. Shibata, S.Mizuta, S.Nakamura, T. Toru,M.Shiro, Angew. Chem. Int. Ed., 2008, 47(42), pp 8051-8054.
[6] W. Lin, S. Zhang, H. He, X. Zhao, L.Dai, S. You, Chem. Commun., 2009, 43, pp 6604-6606.
[7] A. -N.Alba, X. Companyo,R.Rios, Chem. Eur. J. 2009, 15(29), pp 7035-7038.
[8] H.W. Moon, M.J.Cho,D.Y.Kim, Tetrahedron Lett., 2009, 50(34), pp 4896-4898.
[9] T.Furukawa,J.Kawazoe,W.Zhang,T. Nishimine,E.Tokunaga,T. Matsumoto,M.Shiro, N.Shibata, Angew. Chem. Int. Ed., 2011,50(41),pp 9684-9688.
[10] X.Shen,L. Zhang,Y.Zhao,L.Zhu, G.Li,J.Hu, Angew. Chem. Int. Ed.,2011,50(11),pp 2588-2592.
[11] W. Huang, C.Ni, Y.Zhao, J.Hu,New J. Chem.,2013,37(6), pp 1684-1687.
Signal Word
Hazard Statements
Precautionary Statements
HS Code
RIDADR
Legal Information
Warning
H315,H319
P264,P280
2930.90.2900
NONH for all modes of transport

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