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