Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, 350108, Fuzhou, China.
State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, 350108, Fuzhou, China.
Nat Commun. 2020 Oct 21;11(1):5340. doi: 10.1038/s41467-020-19195-w.
Thiols are important precursors for the synthesis of a variety of pharmaceutically important sulfur-containing compounds. In view of the versatile reactivity of free thiols, here we report the development of a visible light-mediated direct decarboxylative thiolation reaction of alkyl redox-active esters to free thiols based on the abundant carboxylic acid feedstock. This transformation is applicable to various carboxylic acids, including primary, secondary, and tertiary acids as well as natural products and drugs, forging a general and facile access to free thiols with diverse structures. Moreover, the direct access to free thiols affords an advantage of rapid in situ diversification with high efficiency to other important thiol derivatives such as sulfide, disulfide, thiocyanide, thioselenide, etc.
硫醇是合成各种具有重要药用价值的含硫化合物的重要前体。鉴于游离硫醇的多功能反应性，我们在此报告了一种可见光介导的直接脱羧硫醇化反应，该反应基于丰富的羧酸原料，可将烷基氧化还原活性酯转化为游离硫醇。这种转化适用于各种羧酸，包括伯、仲和叔酸以及天然产物和药物，为具有各种结构的游离硫醇提供了一种通用且简便的合成方法。此外，直接获得游离硫醇可以快速高效地进行原位多样化，得到其他重要的硫醇衍生物，如硫化物、二硫化物、硫氰化物、硒化物等。
