Abstract
A series of novel chiral bisimidazolium and chiral bis(benzimidazolium) dichlorides with different substituents were synthesised effectively from the corresponding N-substituted imidazoles or N-substituted benzimidazoles with chiral (S)-2,2'-bis(2-chloroethoxy)-1,1'-binaphthalene in solvent-free conditions at ambient pressure. This protocol features a short reaction time, good yields, an eco-friendly process and easily control and handling. These compounds were fully characterised by NMR, IR and elemental analysis, and their specific rotations were given.
References
1.
Díez-González S.
,
Marion N.
, and
Nolan S.P.
, Chem. Rev. , 2009 , 109 , 3612 .
2.
Kuhl O.
, Chem. Soc. Rev. , 2007 , 36 , 592 .
3.
Würtz S.
, and
Glorius F.
, Acc. Chem. Res. , 2008 , 41 , 1523 .
4.
Nolan S.P.
, Acc. Chem. Res. , 2011 , 44 , 91 .
5.
Weskamp T.
,
Schattenmann W.C.
,
Spiegler M.
, and
Herrmann W.A.
, Angew. Chem. Int. Ed. , 1998 , 37 , 2490 .
6.
Hoveyda A.H.
, and
Schrock R.R.
, Chem. Eur. J. , 2001 , 7 , 945 .
7.
Trnka T.M.
, and
Grubbs R.H.
, Acc. Chem. Res. , 2001 , 34 , 18 .
8.
Hillier A.C.
,
Grasa G.A.
,
Viciu M.S.
,
Lee H.M.
,
Yang C.
, and
Nolan S.P.
, J. Organomet. Chem. , 2002 , 653 , 69 .
9.
Lee H.M.
,
Jiang T.
,
Stevens E.D.
, and
Nolan S.P.
, Organometallics , 2001 , 20 , 1255 .
10.
Cesar V.
,
Bellemin-Laponnaz S.
, and
Gade L.H.
, Chem. Soc. Rev. , 2004 , 33 , 619 .
11.
Snead D.R.
,
Seo H.
, and
Hong S.
, Curr. Org. Chem. , 2008 , 12 , 1370 .
12.
Li X.Y.
, and
Nie J.
, Chinese J. Org. Chem. , 2002 , 22 , 840 .
13.
Tamura M.
, and
Fujihara H.
, J. Am. Chem. Soc. , 2003 , 125 , 15742 .
14.
Wang P. Y.
, and
Xiao L.
, J. Mater. Chem. , 2009 , 19 , 8009 .
15.
Stock H. T.
, and
Kellogg R. M.
, J. Org. Chem. , 1996 , 61 , 3093 .
16.
Occhipinti G.
,
Jensen V. R.
, and
Tornroos K. W.
, Tetrahedron , 2009 , 65 , 7186 .
17.
Rosalyn K.
, Tetrahedron Lett. , 2010 , 51 , 5041 .
