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Platinum Metals Rev., 2005, 49, (3), 122
doi: 10.1595/147106705X58970

Highly Active Platinum Phosphinito Homogeneous Catalyst

The hydration of nitriles is a classic reaction in organic chemistry. There are various ways in which nitriles can be activated, but none are as efficient as using a catalyst that combines the advantages of platinum (Pt) ion activation with intramolecular attack. Phosphinito complexes of platinum, in particular [PtH(PMe2OH)(PMe2O)2H], 1, are known as being highly active and versatile for nitrile hydrations (1–3). 1 can catalyse the hydration of acrylonitrile to acrylamide with a turnover number of 77,000 and no tendency of further hydrolysis to the acid. 1 aids preparations of simple amides, not readily prepared by other routes, and of β-blocker, Atenolol.

Now scientists at Harvard University, U.S.A., report that 1 can transform the nitrile group of an epimerised product into the corresponding primary amide (4). In the synthesis of Stephacidin B, 1 was indispensable in a step where a nitrile group of a Strecker-like HCN addition product became a primary amide under neutral conditions. The authors suggest this transformation has scope in the hydrolyses of other Strecker-derived addition products.


  1.  A. W. Parkins, Platinum Metals Rev., 1996, 40, (4), 169
  2.  T. Ghaffar and A. W. Parkins, J. Mol. Catal. A: Chem., 2000, 160, (2), 249 LINK
  3.  X.-B. Jiang, A. J. Minnaard, B. L. Feringa and J. G. de Vries, J. Org. Chem., 2004, 69, (7), 2327 LINK
  4.  S. B. Herzon and A. G. Myers, J. Am. Chem. Soc., 2005, 127, (15), 5342 LINK

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