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Issue 9, 2013
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Thiazolyl-phosphine hydrochloride salts: effective auxiliary ligands for ruthenium-catalyzed nitrile hydration reactions and related amide bond forming processes in water

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Abstract

A series of water-soluble N-protonated thiazolyl-phosphine hydrochloride salts have been synthesized and coordinated to the ruthenium(II) fragment [RuCl26-p-cymene)]. The resulting complexes were evaluated as potential catalysts for the selective hydration of nitriles to primary amides in environmentally friendly aqueous medium. The best results in terms of activity were achieved when tris(5-(2-aminothiazolyl))phosphine trihydrochloride was used as ligand. Using the Ru(II) complex 9 derived from this salt (3 mol%), the catalytic reactions proceeded cleanly in pure water at 100 °C without the assistance of any additive, affording the desired amides in high yields (>78%) after short reaction periods (0.5–7 h). The process was operative with both aromatic, heteroaromatic, α,β-unsaturated and aliphatic nitriles, and tolerated several functional groups. The utility of 9 in promoting the formation of primary amides in water by catalytic rearrangement of aldoximes and direct coupling of aldehydes with NH2OH·HCl has also been demonstrated.

Graphical abstract: Thiazolyl-phosphine hydrochloride salts: effective auxiliary ligands for ruthenium-catalyzed nitrile hydration reactions and related amide bond forming processes in water

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Publication details

The article was received on 20 Jun 2013, accepted on 19 Jul 2013 and first published on 22 Jul 2013


Article type: Paper
DOI: 10.1039/C3GC41201F
Citation: Green Chem., 2013,15, 2447-2456
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    Thiazolyl-phosphine hydrochloride salts: effective auxiliary ligands for ruthenium-catalyzed nitrile hydration reactions and related amide bond forming processes in water

    R. García-Álvarez, M. Zablocka, P. Crochet, C. Duhayon, J. Majoral and V. Cadierno, Green Chem., 2013, 15, 2447
    DOI: 10.1039/C3GC41201F

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