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Platinum Metals Rev., 2005, 49, (3), 122

doi:10.1595/147106705x58970

Highly Active Platinum Phosphinito Homogeneous Catalyst

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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.

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References

  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 http://dx.doi.org/10.1016/S1381-1169(00)00253-3
  3.  X.-B. Jiang, A. J. Minnaard, B. L. Feringa and J. G. de Vries, J. Org. Chem., 2004, 69, (7), 2327 LINK http://dx.doi.org/10.1021/jo035487j
  4.  S. B. Herzon and A. G. Myers, J. Am. Chem. Soc., 2005, 127, (15), 5342 LINK http://dx.doi.org/10.1021/ja0510616

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