Firoozi Somayeh, Hosseini-Sarvari Mona
Department of Chemistry, Shiraz University, Shiraz 7194684795, Islamic Republic of Iran.
J Org Chem. 2021 Feb 5;86(3):2117-2134. doi: 10.1021/acs.joc.0c02263. Epub 2021 Jan 19.
It has been found that the final products of the reaction of sulfonyl chlorides and tertiary amines in the presence of cadmium sulfide nanoparticles under visible light irradiation are highly dependent on the applied reaction conditions. Interestingly, with the change of a reaction condition, different pathways were conducted (visible-light-induced N-dealkylation or sp and sp C-H activation) that lead to different products such as secondary amines and various sulfonyl compounds. Remarkably, all of these reactions were performed under visible light irradiation and an air atmosphere without any additive or oxidant in benign solvents or under solvent-free conditions. During this study, the CdS nanoparticles as affordable, heterogeneous, and recyclable photocatalysts were designed, successfully synthesized, and fully characterized and applied for these protocols. During these studies, intermediates resulting from the oxidation of tertiary amines are trapped during the photoinduced electron transfer (PET) process. The reaction was carried out efficiently with a variety of substrates to give the corresponding products at relatively short times in good to excellent yields in parallel with the use of the visible light irradiation as a renewable energy source. Most of these processes are novel or are superior in terms of cost-effectiveness, safety, and simplicity to published reports.
已发现，在硫化镉纳米粒子存在下，可见光照射下磺酰氯与叔胺反应的最终产物高度依赖于所采用的反应条件。有趣的是，随着反应条件的变化，会进行不同的反应途径（可见光诱导的N-脱烷基化或sp和sp C-H活化），从而导致生成不同的产物，如仲胺和各种磺酰化合物。值得注意的是，所有这些反应都是在可见光照射和空气气氛下，在良性溶剂中或无溶剂条件下，无需任何添加剂或氧化剂进行的。在这项研究中，设计、成功合成并充分表征了作为经济实惠、多相且可回收光催化剂的硫化镉纳米粒子，并将其应用于这些反应方案。在这些研究过程中，叔胺氧化产生的中间体在光诱导电子转移（PET）过程中被捕获。该反应能与多种底物高效进行，在相对较短的时间内以良好至优异的产率得到相应产物，同时使用可见光照射作为可再生能源。这些过程中的大多数在成本效益、安全性和简便性方面都是新颖的或优于已发表的报道。
