2,5-Dihydropyrrole derivatives are considered privileged structures as reflected by their presence in many biologically active molecules and therapeutic agents. Herein, we develop a concise and efficient method utilizing a commercially available copper salt as a catalyst to facilitate the formation of 2,5-dihydropyrroles from propargyl amines and diazo esters. This reaction proceeds via the formation of an N-ylide, followed by bond cleavage/recombination. Control experiments and density functional theory (DFT) calculations provide a detailed analysis of the reaction pathway. The key features of this protocol include simple operation, readily available starting materials, mild conditions, and high atom economy. In addition, the gram-scale preparation experiment and the transformations of 2,5-dihydropyrroles demonstrate the potential applicability of our synthetic method.

中文翻译：

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铜催化重氮酯与炔丙胺的成环反应合成 2,5-二氢吡咯


2,5-二氢吡咯衍生物被认为是特殊结构，这反映在它们存在于许多生物活性分子和治疗剂中。在此，我们开发了一种简洁有效的方法，利用市售的铜盐作为催化剂，促进由炔丙胺和重氮酯形成2,5-二氢吡咯。该反应通过形成 N-叶立德，然后进行键断裂/重组来进行。控制实验和密度泛函理论 (DFT) 计算提供了反应途径的详细分析。该方案的主要特点包括操作简单、起始原料易得、条件温和、原子经济性高。此外，克级制备实验和2,5-二氢吡咯的转化证明了我们的合成方法的潜在适用性。