Platinum-catalyzed selective hydration of hindered Nitriles and nitriles with acid- or base-sensitive groups

被引：139

作者：

Jiang, XB ^{[1
]}

Minnaard, AJ ^{[1
]}

Feringa, BL ^{[1
]}

de Vries, JG ^{[1
]}

机构：

[1] DSM Pharma Chem, NL-6160 MD Geleen, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 07期

关键词：

D O I：

10.1021/jo035487j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hindered tertiary nitriles can be hydrolyzed under neutral and mild conditions to the corresponding amides using platinum(II) catalysts with dimethylphosphine oxide or other secondary phosphine oxides (SPOs, phosphinous acids) as ligands. We have found that this procedure also works well for nitriles with acid- or base-sensitive groups, which is unprecedented in terms of yield and selectivity. The catalyst loading can be as low as 0.5 mol %. Amides are isolated as the only product in high yield, and no further hydrolysis to the corresponding acids takes place. Reactions are carried out at 80 degreesC but take place even at room temperature. When enantiopure secondary phosphine oxide ligands are used in the hydrolysis of racemic nitriles, no kinetic resolution is observed, presumably due to racemization of the ligand during the reaction.

引用

页码：2327 / 2331

页数：5

共 119 条

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