Abstract
An efficient and environmentally benign method for the synthesis of N-sulfonylimines is reported. Condensation of aryl sulfonamides with different aromatic aldehydes and ketones gave N-sulfonylimines in good to excellent yields in the presence of 10 mol% CeCl3 as catalyst. This method can be used with both aldehydes and ketones.
References
1.
Reetz M.T.
,
Jaeger R.
,
Drewlies R.
, and
Hubel M.
, Angew. Chem. Int. Ed. , 1991 , 30 , 103 .
2.
Mancheño O.G.
,
Arrayás R.G.
, and
Carretero J.C.
, J. Am. Chem. Soc. , 2004 , 126 , 456 .
3.
Ooi T.
,
Uematsu Y.
, and
Maruoka K.
, J. Am. Chem. Soc. , 2006 , 128 , 2548 .
4.
Yamanaka M.
,
Nishida A.
, and
Nakagawa M.
, Org. Lett. , 2000 , 2 , 159 .
5.
Yamada K.
,
Fujihara H.
,
Yamamoto Y.
,
Miwa Y.
,
Taga T.
, and
Tomioka K.
, Org. Lett. , 2002 , 4 , 3509 .
6.
Hori R.
,
Aoyama T.
, and
Shioiri T.
, Tetrahedron Lett. , 2000 , 41 , 9455 .
7.
Arini L.G.
,
Sinclair A.
,
Szeto Peter
, and
Stockman R.A.
, Tetrahedron Lett. , 2004 , 45 , 1589 .
8.
Vass A.
,
Dudás J.
, and
Varma R.S.
, Tetrahedron Lett. , 1999 , 40 , 4951 .
9.
Davis F.A.
,
Reddy R.T.
, and
Reddy R.E.
, J. Org. Chem. , 1992 , 57 , 6387 .
10.
Wynne J.H.
,
Price S.E.
,
Rorer J.R.
, and
Stalick W.M.
, Synth. Commun. , 2003 , 33 , 341 .
11.
Jennings W.B.
, and
Lovely C.J.
, Tetrahedron. , 1991 , 47 , 5561 .
12.
Trost B.M.
, and
Marrs C.
, J. Org. Chem. , 1991 , 56 , 6468 .
13.
Suman L.J.
,
Vishal B.S.
, and
Bir S.
, J. Mol. Catal. A: Chem. , 2005 , 239 , 92 .
14.
Jin T.S.
,
Yu M.J.
,
Liu L.B.
,
Zhao Y.
, and
Li T.S.
, Synth. Commun. , 2006 , 36 , 2339 .
15.
Rajesh P.
,
Vishnu P.S.
, and
Lal D.Y.
, Adv. Synth. Catal. , 2010 , 352 , 1610 .
16.
Kaiming W.
,
Zhengwei X.
,
Yudao M.
, and
Qilong W.
, Catal. Lett. , 2008 , 123 , 129 .
17.
Ryosuke M.
,
Florian B.
, and
Shū K
, J. Am. Chem. Soc. , 2008 , 130 , 1804 .
18.
Fan L.Y.
,
Gao F.F.
,
Jiang W.H.
,
Deng M.Z.
, and
Qian C.T.
, Org. Biomol. Chem , 2008 , 6 , 2133 .
19.
John A.M.
,
Mohan M.
,
Gary M.
,
Vijaya Anand R.
,
Thomas M.M.
,
Robert C.
, and
Alan R.K.
, Org. Lett. , 2007 , 9 , 3233 .
20.
Boger D.L.
, and
Corbett W.L.
, J. Org. Chem. , 1992 , 57 , 4777 .
21.
Boger D.L.
, and
Corbett W.L.
, Chem. Ber. , 1964 , 87 , 487 .
22.
Pennings M.L.M.
, and
Reinhoudt D.N.
, Tetrahedron Lett. , 1976 , 21 , 1781 .
23.
Jin T.
,
Feng G.
,
Yang M.
, and
Li T.
, Synth. Commun. , 2004 , 34 , 1277 .
24.
Bartoli G.
,
Fernández-Bolaños J.G.
,
Di Antonio G.
,
Foglia G.
,
Giuli S.
,
Gunnella R.
,
Mancinelli M.
,
Marcantoni E.
, and
Paoletti M.
, J. Org. Chem. , 2007 , 2 , 6029 .
25.
Khmaruk A.M.
, and
Pinchuk A.M.
, Zh. Obsh. Khim. , 1978 , 48 , 1748 .