Compounds consisting of a carbonyl group and an alkyne group, especially enynals and enynones, are versatile and powerful building blocks for generating structurally diverse polycyclic compounds. In the past decades, the transition-metal-catalyzed nucleophilic addition of a carbonyl group to an alkyne has attracted great interest for the high reactivity, good selectivity, excellent functional-group tolerance, and mild reaction conditions. Most importantly, versatile intermediates, such as pyrylium-ion, metal-carbene, 1,3-dipole, and metal-vinyl species, make it highly attractive for both the development of synthetic methodologies and applications in the synthesis of bioactive compounds or complex naturally occurring skeletons. This review focuses on the transition-metal-catalyzed nucleophilic addition of carbonyl groups to alkynes with an emphasis on the scope and limitations, the mechanisms, and applications in organic synthesis.

由羰基和炔基组成的化合物，尤其是烯醛和烯酮，是用于产生结构上多样的多环化合物的通用且功能强大的构建基。在过去的几十年中，羰基过渡金属催化的亲核加成反应引起了人们对高反应活性，良好的选择性，优异的官能团耐受性和温和的反应条件的兴趣。最重要的是，诸如吡啶离子，金属卡宾，1,3-偶极子和金属乙烯基物种之类的通用中间体使其对于合成方法的开发以及在生物活性化合物或天然复合物的合成中的应用都极具吸引力发生的骨骼。