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Synlett 2007(12): 1974-1975  
DOI: 10.1055/s-2007-984876
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Ruthenium(III) Chloride (RuCl3)

Jason T. Lowe*
Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, MA 02215
e-Mail: Jaylowe@bu.edu;
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Publication History

Publication Date:
13 July 2007 (online)

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Introduction

Ruthenium(III) chloride and its hydrate (RuCl3·xH2O) are well-known catalysts for the oxidation of functional groups in organic synthesis. Some of these transformations include: alkenes to diols [1] and α-hydroxyketones, [2] sulfides to sulfones, [3] as well as alkynes, [4] alcohols [5] and aryl groups [6] to their corresponding carboxylic acids. The titled catalyst has also been used for the desymmetrization of aryl and benzyl diselenides, [7] aldol condensation, [8] ­formation of α-aminonitriles (Strecker reaction), [9] acylation, [10] acetal formation, [11] aryl [12] or azide [13] reductions, conjugate addition reactions [14] and C-C bond formations. [15]

Apart from the use of ruthenium(III) chloride in functional group manipulation, recent work has used RuCl3 in the formation of polypyridine complexes, suggesting that this reagent may soon experience a wider application in ­metallopolymer and molecular-device synthesis. [16]

Ruthenium(III) chloride is also a critical ingredient for preparing a number of ruthenium-based catalysts, including Grubbs’ catalysts (widely applied in metathesis reactions) [17] and ruthenium-phosphine complexes capable of selective reductions. [18]

Both anhydrous and hydrated forms are commercially available as solids. Alternatively, the solids may be ­prepared by heating powdered ruthenium metal to temperatures greater than 700 °C in the presence of chlorine gas; on cooling, dark brown to black crystals may form. [19] ­Although their hygroscopic nature mandates storage in desiccated environments, no additional precautions are ­required for safe handling.