Wang Yakun, Liu Jie, Wang Yingying, Du Xiaoyu, Song Haojie, Fang Lizhen, Wu Liqiang, Zhang Tao
School of Pharmacy, Xinxiang Medical University, Xinxiang, Henan 453003, P. R. China.
J Org Chem. 2024 Mar 1;89(5):3453-3470. doi: 10.1021/acs.joc.3c02896. Epub 2024 Feb 9.
In the present study, we successfully developed an efficient thiocyanation of carbonyl compounds by using low-toxicity and inexpensive ammonium thiocyanate as the thiocyanate source under visible light in air (O) at room temperature. This unified strategy is very facile for thiocyanation of various carbonyl compound derivatives (β-keto esters, β-keto amides, pyrazo-5-ones, isoxazol-5-ones, etc.). More importantly, the reaction proceeded smoothly without the addition of a photocatalyst and strong oxidant, ultimately minimizing the production of chemical waste. Furthermore, this green and sustainable synthetic chemistry can be used in the late-stage functionalization (LSF) of biorelevant compounds, which offers unique opportunities to achieve smooth and clean thiocyanation of drugs under mild reaction conditions.
在本研究中，我们成功开发了一种高效的羰基化合物硫氰化反应，该反应在室温下于空气中（氧气）可见光条件下，使用低毒性且廉价的硫氰酸铵作为硫氰酸源。这种统一的策略对于各种羰基化合物衍生物（β-酮酯、β-酮酰胺、吡唑-5-酮、异恶唑-5-酮等）的硫氰化反应非常简便。更重要的是，该反应无需添加光催化剂和强氧化剂即可顺利进行，最终将化学废物的产生降至最低。此外，这种绿色且可持续的合成化学可用于生物相关化合物的后期功能化（LSF），这为在温和反应条件下实现药物的顺利且清洁的硫氰化反应提供了独特的机会。
