Abstract
An ionic liquid based on 1-butyl-3-methylimidazolium tetrafluoroborate (BmimBF4) is used as a reusable reaction medium for the alkylation of sodium arenesulfinates with alkyl halides. This procedure is convenient, efficient and generally gives rise to the S-alkylated product with high selectivity when applied to active halides.
References
1.
(a)
Magnus P.D.
, Tetrahedron , 1977 , 33 , 2019 .
2.
Simpkins N-S.
, Sulfones in Organic Synthesis in Tetrahedron Organic Chemistry Series Vol. 10 ,
Baldwin J.E.
, and
Magnus P. D.
, Ed. Pergamon Press , Oxford , 1993 .
3.
Najer C.
, and
Yus M.
, Tetrahedron , 1999 , 55 , 10547 .
4.
Trost B.M.
, and
Schmuff N. R.
, J. Am. Chem. Soc. , 1985 , 107 , 396 and references cited therein.
5.
(a)
Trost B.M.
, and
Braslau R.
, J. Org. Chem. , 1988 , 53 , 532 .
6.
Sato K.
,
Hyodo M.
,
Aoki M.
,
Zheng X.- Q.
, and
Noyori R.
, Tetrahedron , 2001 , 57 , 2469 .
7.
(a)
Sun X.H.
,
Wang L.
, and
Zhang Y. M.
, Synth. Commun. , 1998 , 28 , 1785 .
8.
Li H.B.
,
Wang H.
,
Pan Y.
, and
Shi Y. Z.
, Synth. Commun. , 1998 , 28 , 409 .
9.
Vennstra G.E.
, and
Zwanenburg B.
, Synthesis , 1975 , 519 .
10.
Manescalchi F.
,
Orena M.
, and
Savoia D.
, Synthesis , 1979 , 445 .
11.
(a)
Crandall J.K.
, and
Pradat C.
, J. Org. Chem. , 1985 , 50 , 1327 .
12.
Bram G.
,
Loupy A.
,
Roux-Schmit M. C.
,
Sansoulet J.
,
Strzalk T.
, and
Jacqueline S.-P.
, Synthesis , 1987 , 56 .
13.
Ramaiah K.
,
Dubey P. K.
,
Ramanatham J.
,
Grossert J. S.
, and
Hooper D. L.
, Ind. J. Chem., Sect., B 1999 , 38B (3 ), 297 .
14.
Wildeman J.
, and
Leusen A. M. V.
, Synthesis , 1979 , 733 .
15.
Biswas G.K.
,
Chakrabarty M.
, and
Bhattacharyya P.
, Ind. J. Chem., Sect., B , 1991 , 30B (11 ), 1059 .
16.
Li Y.Q.
, Chem. Res. Appl. , 1997 , 9 , 311 .
17.
Murakami T.
, and
Furusawa K.
, Synthesis , 2002 , 479 .
18.
(a)
Villemin D.
, and
Alloum A. B.
, Synth. Commun. , 1990 , 20 , 925 .
19.
Biswas G.K.
,
Jash S. S.
, and
Bhattacharyya P.
, Ind. J. Chem., Sect., B 1990 , 29B (5 ), 491 .
20.
(a)
Welton T.
, Chem. Rev. , 1999 , 99 , 2071 .
21.
Wasserscheid P.
, and
Keim W.
, Angew. Chem. Int. Ed. Engl. , 2000 , 39 , 3772 .
22.
Sheldon R.
, Chem. Commum. , 2001 , 2399 .
23.
Jairton D.
,
Robeerto F.
, and
Paulo A. Z. S.
, Chem. Rev. , 2002 , 102 , 3667 .
24.
Zhao D.
,
Wu M.
,
Kou Y.
, and
Min E.
, Catal Today , 2002 , 74 , 157 .
25.
Wasserscheid P.
, and
Welton T.
, (eds) Ionic Liquids in Synthesis , VCH Wiley , Weinheim, Germany , 2002 .
26.
Meek J.S.
, and
Fowler J. S.
, J. Org. Chem. , 1968 , 33 , 3422 .
27.
Shriner R.L.
,
Struck H. C.
, and
Jorison W. J.
, J. Am. Chem. Soc. , 1930 , 52 , 2069 .
28.
Kice J.L.
, and
Lidia K.S.
, J. Org. Chem. , 1991 , 56 , 1424 .
29.
Owens G.S.
, and
Abu-Omer M. M.
, J. Mol. Catal. A: Chem. , 2002 , 187 , 211 .
30.
Furukawa M.
,
Ohkawara T.
,
Noguchi Y.
,
Isoda M.
, and
Hitoshi T.
, Synthesis , 1980 , 937 .
31.
Evans D.A.
,
Faul M. M.
,
Colombo L.
,
Bisaha J. J.
,
Clardy J.
, and
Cherry D.
, J. Am. Chem. Soc. , 1992 , 114 , 5977 .
