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DOI: 10.1055/s-2007-967961
Al-NiCl2·6H2O: A Mild and Efficient System for Selective Reduction of Functional Groups in Organic Synthesis
Publication History
Publication Date:
08 March 2007 (online)
Introduction
The most common broad-spectrum reducing agents are metal hydrides like LiAlH4, NaBH4, DIBAL-H, and 9-BBN. Apart from this, some hydrogenation catalysts have been investigated in order to find conditions under which a given group will be reduced chemoselectively. [1] Metal-metal-salt binary systems such as Al-NiCl2·6H2O·THF, [2] Al-SbCl3 or Zn-SbCl3, [3] Fe-NiCl2·6H2O·THF, [4] or Sm-NiCl2·6H2O·THF [5] have long been used as reducing agents for many functional groups.
Reagents based on aluminum find wide application in organic synthesis. [6] The Al-NiCl2·6H2O system is a highlight in current organic chemistry due to its selectivity, mild reaction conditions, easy handling, low cost, and convenient isolation process.
- 1
March J. Advanced Organic Chemistry 4th ed.: John Wiley & Sons; New York: 1992. p.1206 ;and references cited therein - 2
Sarmah BK.Barua NC. Tetrahedron 1991, 47: 8587 - 3
Wang WB.Shi LL.Huang YZ. Tetrahedron Lett. 1990, 31: 1185 - 4
Barua M.Boruah A.Prajapati D.Sandhu JS. Tetrahedron Lett. 1996, 37: 4559 - 5
Wu H.Chen R.Zhang Y. Synth. Commun. 2002, 32: 189 - 6
Chen JG.Beebe TP.Crowell JE.Yates JT. J. Am. Chem. Soc. 1987, 109: 1726 - 7
Hazarika MJ.Barua NC. Tetrahedron Lett. 1989, 30: 6567 - 8
Sarmah P.Barua NC. Tetrahedron Lett 1990, 31: 4065 - 9
Hu QS.Hu CM. J. Fluorine Chem. 1996, 76: 117 - 10
Bezbarua MS.Bez G.Barua NC. Chem. Lett. 1999, 325 - 11
Kamal A.Reddy KL.Devaiah V.Reddy GSK. Tetrahedron Lett. 2003, 44: 4741 - 12
Raju BR.Devi G.Nongpluh YS.Saikia AK. Synlett 2005, 358