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Synlett 2003(2): 0279-0280
DOI: 10.1055/s-2003-36809
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© Georg Thieme Verlag Stuttgart · New York

NiCl2 and NiCl2 = 6H2O: A very Useful Mild Lewis Acid in Organic Synthesis

Philippe Labrie*
Department of Chemistry, Universitè Laval, Quebec G1K 7P4, Canada
e-Mail: plabrie16@hotmail.com;
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Publication History

Publication Date:
22 January 2003 (online)

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Introduction

Lewis acids are very useful reagents in organic synthesis. The classical Lewis acids currently used include BF3 ·ΟEt2, ZnCl2, SnCl2, TiCl4 and many others. Nickel chloride can be also added to this list. NiCl2 is a mild Lewis acid that promotes a wide variety of organic transformations in aqueous medium or organic solvent and may be used either catalytically or stoichiometrically. NiCl2 was also used in a key step in the synthesis of bi­benzopyran-4-ol, [1] tetrahydrodicranenone B [2] and Allo­pumiliotoxins. [3] NiCl2 is a selective reductive agent when used with hydrides such as LiAlH4 and NaBH4. In fact, the mixture of NiCl2 and NaBH4 is used to prepare nickel boride, [4] a reducing agent for many functional groups: azide, [5] nitrile, [6] NO bond, [7] alkene [8] and haloalkane. [9] NiCl2 was used in the regioselective rearrangement of dienols, [10] ring-opening of epoxide, [11] nickel(II)/chromium(II) chlor­ide-mediated addition to aldehydes or ketones, [2] [3] Suzuki cross-coupling, [12] Biginelli reaction, [13] reductive Heck-like reactions, [14] nickel-catalyzed cross-coupling reaction of Grignard reagents [15] and homo-coupling reactions. [16]