Equipe Chimie Moléculaire, Laboratoire de Génomique, Bioinformatique et Chimie Moléculaire, (GBCM), EA 7528, Conservatoire National des Arts et Métiers, Hautes Écoles Sorbonne Arts et Métiers (HESAM) Université, Paris 2 rue Conté, 75003, France.
Laboratoire de Chimie, ENS de Lyon, CNRS UMR 5182, Université Claude Bernard Lyon 1, Lyon F-69342, France.
J Org Chem. 2023 May 19;88(10):6498-6508. doi: 10.1021/acs.joc.2c03014. Epub 2023 Mar 29.
Visible light photooxidation of naphthols to produce naphthoquinones, such as the natural product juglone, has been known for decades and has been widely utilized to benchmark the performances of a variety of photocatalytic systems. We discovered that these transformations can occur without the help of a photocatalyst and, even more intriguingly, that the photocatatyst-free process provides higher yields compared to control experiments utilizing state-of-the-art photocatalysts. In addition, we demonstrate that naphthoquinones and their corresponding naphthol precursors can act as alternatives to commonly used organic and organometallic photocatalysts with applications to challenging targets, such as the antimalarial drug artemisinin. This approach was finally transposed in continuous flow reactors where high photocatalyst stability and process efficiency are demonstrated with a 23× improvement in the space-time yield.
可见光促进萘酚氧化生成萘醌，例如天然产物胡桃醌，这一过程已被人们认识了几十年，并被广泛用于各种光催化体系性能的基准测试。我们发现，这些转化可以在没有光催化剂的帮助下发生，更有趣的是，与利用最先进的光催化剂进行的对照实验相比，无催化剂的过程提供了更高的产率。此外，我们证明了萘醌及其相应的萘酚前体可以替代常用的有机和有机金属光催化剂，应用于具有挑战性的目标，如抗疟药物青蒿素。最后，我们将这种方法转化为连续流反应器中，在那里高的光催化剂稳定性和过程效率得到了证明，时空收率提高了 23 倍。
