Abstract
A mild and efficient method for the formation of C–N bonds is reported with SnCl4 as an inexpensive catalyst. With 10 mol% of SnCl4, the direct substitution reaction of secondary benzyl alcohols with a sulfonamide, a carboxamide, 4-nitroaniline and an azide proceeds well in good to excellent yields at room temperature.
References
1.
Ricci A.
, Modern amination methods , Wiley-VCH , Weinheim, Germany , 2000 .
2.
Jana U.
,
Maiti S.
, and
Biswas S.
, Tetrahedron Lett. , 2008 , 49 , 858 .
3.
Qin H.
,
Yamagiwa N.
,
Matsunaga S.
, and
Shibasaki M.
, Angew. Chem. , 2007 , 119 , 413 .
4.
Terrasson V.
,
Marque S.
,
Georgy M.
,
Campagne J.-M.
, and
Prim D.
, Adv. Synth. Catal. , 2006 , 348 , 2063 .
5.
Motokura K.
,
Nakagiri N.
,
Mizugaki T.
,
Ebitani K.
, and
Kaneda K.
, J. Org. Chem. , 2007 , 72 , 6006 .
6.
Raji Reddy Ch.
,
Phani Madhavi P.
, and
Syamprasad Reddy A.
, Tetrahedron Lett. , 2007 , 48 , 7169 .
7.
Li L.
,
Zhang G.
,
Zhu A.
, and
Zhang L.-H.
, J. Org. Chem. , 2008 , 73 , 3630 .
8.
Zhu A.
,
Jiang T.
,
Han B.
,
Zhang J.
,
Xie Y.
, and
Ma X.
, Green Chem. , 2007 , 9 , 169 .
9.
Zhang X.
,
Li L.
, and
Zhang G.
, Green Chem. , 2003 , 5 , 646 .
10.
Li L.
,
Zhu L.
,
Zhang G.
, and
Qu G.
, Can. J. Chem. , 2005 , 83 , 1120 –1123 .
11.
Grynkiewicz G.
,
Priebe W.
, and
Zamojski A.
, Carbohydr. Res. , 1979 , 68 , 33 –41 .
12.
Uenishi J.
,
Takahashi K.
,
Motoyama M.
,
Akashi H.
,
Sasaki T.
, Nucleosides, Nucleotides Nucleic Acids , 1994 , 13 , 1347 .
13.
Tuzina P.
, and
Somfai P.
, Tetrahedron Lett. , 2008 , 49 , 6882 .
14.
Oi S.
,
Moro M.
,
Fukuhara H.
,
Kawanishi T.
, and
Inoue Y.
, Tetrahedron , 2003 , 59 , 4351 .
15.
Noji M.
,
Ohno T.
,
Fuji K.
,
Futaba N.
,
Tajima H.
,
Ishii K.
, J. Org. Chem. , 2003 , 68 , 9340 .
16.
Maki T.
,
Ishihara K.
,
Yamamoto H.
, Org. Lett. , 2003 , 8 , 1431 .
17.
Kondo K.
,
Sekimoto E.
,
Nakao J.
,
Murakami Y.
, Tetrahedron , 2000 , 56 , 5843 .