Abstract
A Brønsted acidic deep eutectic solvent based on choline chloride and p-toluenesulfonic acid (ChCl/p-TsOH, 1:1) was prepared and utilised for the selective oxidation of sulfides with H2O2 as the oxidant. Broad substrate compatibility, good yields and selectivities, the reusability of the catalyst as well as the gram-scale synthesis are the major advantages of this protocol. Moreover, the use of ChCl/p-TsOH, instead of neat p-TsOH, can greatly reduce the acid sewage especially in large-scale synthetic processes.
References
1.
Fernandez I.
, and
Khiar N.
, Chem. Rev. , 2003 , 103 , 3651 .
2.
Sato K.
,
Huodo M.
,
Aoki M.
,
Zhang X.Q.
, and
Noyori R.
, Tetrahedron , 2001 , 57 , 2469 .
3.
Karimi B.
,
Ghoreishi-Nezhad M.
, and
Clark J.H.
, Org. Lett. , 2005 , 7 , 625 .
4.
Wu Y.
,
Liu J.
,
Li X.
, and
Chan A.S.C.
, Eur. J. Org. Chem. , 2009 , 2607 .
5.
Yamaguchi T.
,
Matsumoto K.
,
Saito B.
, and
Katsuki T.
, Angew. Chem. Int. Ed. , 2007 , 46 , 4729 .
6.
Egami H.
, and
Katsuki T.
, J. Am. Chem. Soc. , 2007 , 129 , 8940 .
7.
Bravo A.
,
Dordi B.
,
Fontana F.
, and
Minisci F.
, J. Org. Chem. , 2001 , 66 , 3232 .
8.
Habibi D.
,
Zolfigol M.A.
,
Safaiee M.
,
Shamsian A.
, and
Ghorbani-Choghamarani A.
, Catal. Commun. , 2009 , 10 , 1257 .
9.
Legros J.
,
Delhi J.R.
, and
Bolm C.
, Adv. Synth. Catal. , 2005 , 347 , 19 .
10.
Rajabi F.
,
Naserian S.
,
Primo A.
, and
Luquc R.
, Adv. Synth. Catal. , 2011 , 353 , 2060 .
11.
Prasanth K.L.
, and
Maheswaran H.
, J. Mol. Catal. A , 2007 , 268 , 45 .
12.
Pordea A.
,
Mathis D.
, and
Ward T.R.
, J. Organomet. Chem. , 2009 , 694 , 930 .
13.
Firouzabadi H.
,
Abbassi M.
, and
Karimi B.
, Synth. Commun. , 1999 , 29 , 561 .
14.
Bonadies F.
,
De Angelis F.
,
Locati L.
, and
Scettri A.
, Tetrahedron Lett. , 1996 , 37 , 7129 .
15.
Golchoubian H.
, and
Hosseinpoor F.
, Molecules , 2007 , 12 , 304 .
16.
Jafari H.
,
Rostami A.
,
Ahmad-Jangi F.
, and
Ghorbani-Choghamarani A.
, Synth. Commun. , 2012 , 42 , 3150 .
17.
Rostami A.
,
Hassanian F.
,
Ghorbani-Choghamarani A.
, and
Saadati S.
, Phosphorus Sulfur, Silicon , 2013 , 188 , 833 .
18.
Sonawane Y.A.
,
Phadtare S.B.
,
Borse B.N.
,
Jaqtap A.R.
, and
Shankarling G.S.
, Org. Lett. , 2010 , 12 , 1456 .
19.
Imperato G.
,
Vasold R.
, and
Konig B.
, Adv. Synth. Catal. , 2006 , 348 , 2243 .
20.
Phadtare S.B.
, and
Shankarling G.S.
, Green Chem. , 2010 , 12 , 458 .
21.
Singh B.
,
Lobo H.
, and
Shankarling G.S.
, Catal. Lett. , 2011 , 141 , 178 .
22.
Lindberg D.
,
Revenga M.F.
, and
Widersten M.
, J. Biotechnol. , 2010 , 147 , 169 .
23.
Zheng W.R.
,
Xu J.L.
,
Huang T.
,
Yang Q.
, and
Chen Z.C.
, Res. Chem. Intermed. , 2011 , 37 , 31 .
24.
Singh B.S.
,
Loba H.R.
, and
Shankarling G.S.
, Catal. Commun. , 2012 , 24 , 70 .
25.
Patil U.B.
,
Shendage S.S.
, and
Nagarkar J.M.
, Synlett , 2013 , 45 , 3295 .
26.
Wang L.
,
Dai D.Y.
,
Chen Q.
, and
He M.Y.
, Asian J. Org. Chem. , 2013 , 2 , 1040 .
27.
Durand E.
,
Lecomte J.
,
Baréa B.
,
Dubreucq E.
,
Lortiec R.
, and
Villeneuvea P.
, Green Chem. , 2013 , 15 , 2275 .
28.
Bahrami K.
,
Khodaei M.M.
, and
Fattahpour P.
, Catal. Sci. Technol. , 2011 , 1 , 389 .
29.
Choudary B.M.
,
Bharathi B.
,
Reddy C.V.
, and
Kantam M.L.
, J. Chem. Soc. Perkin. Trans. 1 , 2002 , 2069 .
30.
Lakouraj M.M.
,
Tajbakhsh M.
, and
Tashakkorian H.
, Monatsh. Chem. , 2007 , 138 , 83 .
31.
Chen Z.
,
Zhou B.
,
Cai H.
,
Zhu W.
, and
Zhou X.
, Green Chem. , 2009 , 11 , 275 .
