Journal
ORGANOMETALLICS
Volume 30, Issue 20, Pages 5442-5451Publisher
AMER CHEMICAL SOC
DOI: 10.1021/om2006563
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Funding
- Spanish Ministry of Science and Innovation (MICINN) [CTQ2010-14796/BQU, CSD2007-00006]
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The catalytic hydration of nitriles into amides, in water under neutral conditions, has been studied using a series of arene-ruthenium(II) derivatives containing the commercially available and inexpensive ligand tris(dimethylamino)phosphine. Among them, best results were obtained with the complex [RuCl2(eta(6)-C6Me6){P(NMe2)(3)}], which selectively provided the desired amides in excellent yields and short times (TOF values up to 11 400 h(-1)). The process was operative with both aromatic, heteroaromatic, aliphatic, and alpha,beta-unsaturated organonitriles and showed a high functional group tolerance. The stability of [RuCl2(eta(6)-C6Me6){P(NMe2)(3)}] in water was evaluated, observing its progressive decomposition into the less-active dimethylamine nithenium(II) complex [RuCl2(eta(6)-C6Me6)(NHMe2)] by hydrolysis of the coordinated P(NMe2)(3) ligand. The X-ray crystal structure determination of the toluene complex [RuCl2(eta(6)-C6H5Me){P(NMe2)(3)}] is also included.
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