Gentile Giuseppe, Morant-Giner Marc, Cardo Lucia, Melchionna Michele, Fornasiero Paolo, Prato Maurizio, Filippini Giacomo
Department of Chemical and Pharmaceutical Sciences, INSTM UdR Trieste, University of Trieste, via Licio Giorgieri 1, 34127, Trieste, Italy.
Instituto de Ciencia Molecular (ICMol), Universitat de València, C/Catedrático José Beltrán 2, 46980, Paterna, Spain.
ChemSusChem. 2023 Nov 8;16(21):e202300831. doi: 10.1002/cssc.202300831. Epub 2023 Aug 21.
2H-MoS is an appealing semiconductor because of its Earth-abundant nature, cheapness, and low toxicity. This material has shown promising catalytic activity for various energy-related processes, but its use in catalysis for C-C bond forming reactions towards useful organic compounds is still largely unexplored. The lack of examples in organic synthesis is mainly due to the intrinsic difficulties of using bulk 2H-MoS (e. g., low surface area), which implies the reliance on high catalytic loadings for obtaining acceptable yields. This makes the optimization process more expensive and tedious. Here, we report the development of a 2H-MoS -mediated synthesis of valuable bis(indolyl)methane derivatives, using indoles and benzaldehydes as starting materials. Exploiting the Design of Experiments (DoE) method, we identified the critical parameters affecting the catalytic performance of commercial 2H-MoS powder and optimized the reaction conditions. Lastly, we demonstrated that the catalytic system has versatility and good tolerance towards functional group variations of the reagents.
二硫化钼（2H-MoS）因其在地壳中储量丰富、价格低廉且毒性低，是一种具有吸引力的半导体。这种材料已在各种与能源相关的过程中显示出有前景的催化活性，但其在用于形成有用有机化合物的碳 - 碳键形成反应的催化方面仍未得到充分探索。有机合成中缺乏相关实例主要是由于使用块状二硫化钼（例如，低表面积）存在内在困难，这意味着要获得可接受的产率依赖于高催化负载量。这使得优化过程更加昂贵和繁琐。在此，我们报道了一种以二硫化钼介导的、以吲哚和苯甲醛为起始原料合成有价值的双（吲哚基）甲烷衍生物的方法。利用实验设计（DoE）方法，我们确定了影响市售二硫化钼粉末催化性能的关键参数，并优化了反应条件。最后，我们证明了该催化体系对试剂的官能团变化具有通用性和良好的耐受性。
