在《有机化学快报》上发表的一项创新研究中，由梁雷、牛红英、李仁龙、王耀飞、严谨开、李长恭和郭海明组成的研究团队，成功开发了一种通过芳基硫鎓盐进行的光诱导铜催化C(sp2)−C(sp)位点选择性交叉偶联方法。这一方法描述了从多样化的芳烃派生的芳基硫鎓盐出发，高选择性和高功能团兼容性地合成芳基炔烃的新途径。此外，该方法还展示了药物分子的快速炔基化。
该研究在有机合成领域具有重大意义，尤其是在制药、大环化合物、分子有机材料和天然产物的合成中。通过采用非贵金属铜作为催化剂，并结合光还原技术，这一新方法不仅提高了化学选择性，还扩展了反应底物的范围，对于敏感功能团（例如烯烃、酯、腈或杂环团）含有的芳烃也展示了高度的化学选择性和功能团容忍性。这一工作在金属催化的C(sp2)−C(sp)偶联反应领域开辟了新的途径，并为多功能化的芳基炔烃的构建提供了简便的合成策略。
[CN], 2020 — A groundbreaking study published in "Organic Letters" by the research team consisting of Lei Liang, Hong-Ying Niu, Ren-Long Li, Yao-Fei Wang, Jin-Kai Yan, Chang-Gong Li, and Hai-Ming Guo, has developed a novel photoinduced copper-catalyzed site-selective C(sp2)−C(sp) cross-coupling method via aryl sulfonium salts. This method delineates a new pathway for synthesizing arylalkynes with high selectivity and high functional-group compatibility, starting from diverse arenes derived from aryl sulfonium salts. Moreover, it demonstrates the rapid alkynylation of drug molecules.
This research holds significant implications in the field of organic synthesis, especially in the synthesis of pharmaceuticals, macrocycles, molecular organic materials, and natural products. By employing non-noble metal copper as the catalyst combined with photoredox techniques, this new method not only enhances chemoselectivity but also broadens the substrate scope. It shows a high level of chemoselectivity and functional group tolerance for arenes containing sensitive functional groups such as alkenes, esters, cyano, or heterocyclic groups. This work opens new avenues in the field of metal-catalyzed C(sp2)−C(sp) coupling reactions and offers a facile synthesis strategy for the construction of diversely functionalized arylalkynes.
https://pubs.acs.org/doi/10.1021/acs.orglett.0c02364