Metalated nitriles are exceptional nucleophiles capable of forging highly hindered stereocenters in cases where enolates are unreactive. The excellent nucleophilicity emanates from the powerful inductive stabilization of adjacent negative charge by the nitrile, which has a miniscule steric demand. Inductive stabilization is the key to understanding the reactivity of metalated nitriles because this permits a continuum of structures that range from N-metalated ketenimines to nitrile anions.

中文翻译：

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C和N金属化的腈：结构与选择性之间的关系

金属化的腈是特殊的亲核试剂，在烯醇不发生反应的情况下，它们能够锻造高度受阻的立体中心。优异的亲核性源自腈对相邻负电荷的强大感应稳定作用，而对空间的需求微乎其微。感应稳定化是理解金属腈的反应性的关键，因为它允许从N金属化的酮亚胺到腈阴离子的连续结构。