The incorporation of alkynes into organic molecules is one of the most valuable transformations for the formation of C–C bonds and provides a versatile handle for further modifications. The Sonogashira cross-coupling of acetylenes holds a prominent position among the suite of catalytic cross-coupling reactions that are key to modern synthesis. Here we present a method that is complementary to the Sonogashira reaction, demonstrating cross-coupling of lithium acetylides with aryl bromides. The reactions take place under ambient conditions with short reaction times, affording the corresponding aryl acetylenes in good to excellent yields while displaying a remarkable functional group tolerance for an organolithium reaction, allowing the presence of a variety of organolithium-sensitive carbonyl functionalities. This developed cross-coupling methodology offers ample opportunities to access a wide variety of acetylenes, as is illustrated by the facile preparation of key intermediates for chemical biology and optoelectronic materials.

将炔烃掺入有机分子是形成C–C键的最有价值的转化之一，并为进一步修饰提供了一种通用的方法。乙炔的Sonogashira交叉偶联在一系列催化交叉偶联反应中占有重要地位，这是现代合成的关键。在这里，我们提出了一种与Sonogashira反应互补的方法，证明了乙炔锂与芳基溴的交叉偶联。反应在环境条件下以短的反应时间进行，以良好的产率至优异的产率提供相应的芳基乙炔，同时对有机锂反应显示出显着的官能团耐受性，从而允许存在多种有机锂敏感的羰基官能团。