Alkynes have played pivotal roles in numerous synthetic transformations and materials science. Here, by developing nitrogen-deletion coupling, we describe a modular synthesis of alkynes from widely accessible nitriles by swapping the N atom to a C atom in cyano groups, where lithiated gem-diborylalkanes and tert-butyl nitrite are applied sequentially. NMR analysis and crystal structure show the nature of an intermediary α-boryl lithium enamine. A diverse range of nitriles are converted into various internal and terminal alkynes within a short reaction time, including alkynes bearing bulky secondary and tertiary alkyl substituents on both sides.

中文翻译：

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通过与 gem-二硼烷烃的氮缺失偶联实现三键原子交换


炔烃在许多合成转化和材料科学中发挥了关键作用。在这里，通过开发氮缺失耦合，我们描述了一种由广泛可及的腈模块化合成炔烃的方法，方法是在氰基中将 N 原子交换为 C 原子，其中锂化的 gem-二硼烷烃和亚硝酸叔丁酯依次施加。NMR 分析和晶体结构显示了中间 α-硼基烯胺锂的性质。各种腈在短反应时间内转化为各种内炔和末端炔烃，包括两侧都带有大体积的仲和叔烷基取代基的炔烃。