C(sp2)–S cross-coupling reactions with nickel, visible light, and mesoporous graphitic carbon nitride†

Abstract

Cross-coupling reactions play a vital role in modern organic synthesis, enabling the construction of necessary C–C or C–(het)atom bonds for synthetic transformations. Although C(sp²)–C and C(sp²)–N cross-coupling reactions have received significant attention, recent advancements have also highlighted the significance of C(sp²)–S cross-coupling reactions. These reactions lead to the synthesis of valuable compounds, including pharmaceuticals and materials. In a recent report, we introduced Adaptive Dynamic Homogeneous Catalysis (AD-HoC) as an efficient method for C(sp²)–S cross-coupling reactions. This method operates without the need for any ligands, base, or additional additives, relying solely on essential parameters. In this report, we discuss the use of mesoporous graphitic carbon nitride (mpg-CN) as an all-organic heterogeneous photocatalyst in such transformations. The versatility and robustness of the reaction are showcased with fifty synthetic examples, achieving up to a 98% yield. The use of mpg-CN as a catalyst additionally enables the easy recovery of the photocatalyst from the reaction mixture and facilitates the sequential execution of multiple cross-coupling reactions with consistent yields of the desired products using a simple setup. This approach is a significant advancement in the field, both in terms of operational simplicity and environmental impact, traits that we all envision for sustainability.