As one of the most efficient and straightforward strategies for the synthesis of organic compounds, transition-metal mediated C−H bond functionalization has received significant attention in recent years and has become a powerful methodology. Although C-H bond functionalization with the presence of a directing group to enhance the reactivity and selectivity has been widely explored, reports with challenging substrates, such as arenes with one or two halogen substitution, are still limited. Because the reactivity of arenes paralleled the acidity of the C-H bond in the CMD process, usage of brominated arenes as substrates commonly leads to poor site-selectivity and reluctant reactivity. In our research on silver catalyzed H/D exchange reaction, we found the C-H bond of brominated arenes can be easily activated by the combination of silver salt and phosphine ligand. This result promoted us to explore the direct CH bond functionalization of brominated arenes with the combination of silver and palladium as catalyst. Herein, we presented direct arylation of brominated benzene, pyridine and thiophene with iodoarenes as coupling partners. The coupling products, brominated bi-arenes, can be served as useful synthons for electronic materials, drug candidates and conjugated polymers.

Direct arylation of brominated arenes

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