Wang Qian, Zhang Cheng-Lin, Li Yan-Fei, Zhou Yu-Jing, Cui Fei-Hu, Jiang Jing-Chen, Pan Ying-Ming, Duan Wen-Gui, Tang Hai-Tao
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, 541004, People's Republic of China.
School of Chemistry and Chemical Engineering, Guangxi University, Nanning, 530004, People's Republic of China.
Chemistry. 2024 Dec 5;30(68):e202402716. doi: 10.1002/chem.202402716. Epub 2024 Oct 16.
Dithiocarbamate is a key structural sequence in pharmaceuticals and agrochemicals, and its synthesis is crucial in organic chemistry. Although significant progress has been made in related synthesis research, developing a practical and universal synthesis method remains fascinating. Herein, we report a new visible-light-induced decarboxylation coupling reaction between N-hydroxyphthalimide esters and tetraalkylthiuram disulfides, which uses Ir(ppy) as a photocatalyst to promote the generation of corresponding decarboxylation thioacylation product-dithiocarbamates in high yields. This redox-neutral protocol uses inexpensive and readily available starting material under mild reaction conditions, exhibiting broad substrate scope and wide functional group compatibility. This method can be further used for post modification of complex natural products and bioactive drugs.
二硫代氨基甲酸盐是药物和农用化学品中的关键结构序列，其合成在有机化学中至关重要。尽管相关合成研究已取得显著进展，但开发一种实用且通用的合成方法仍然具有吸引力。在此，我们报道了一种新型的可见光诱导的N-羟基邻苯二甲酰亚胺酯与四烷基二硫化秋兰姆之间的脱羧偶联反应，该反应使用Ir(ppy)作为光催化剂，以高产率促进生成相应的脱羧硫酰化产物——二硫代氨基甲酸盐。这种氧化还原中性的方法在温和的反应条件下使用廉价且易于获得的起始原料，展现出广泛的底物范围和良好的官能团兼容性。该方法可进一步用于复杂天然产物和生物活性药物的后期修饰。
