Palladium-catalyzed denitrative N-arylation of nitroarenes with pyrroles, indoles, and carbazoles

We have developed an efficient palladium-catalyzed denitrative N-arylation via cross-coupling of N-H heteroarenes with nitroarenes, one of the most inexpensive and fundamental feedstocks in the chemical industry. A variety of functionalized N-arylated heterocycles could be selectively synthesized in moderate to excellent yields. Furthermore, the success of the scale-up experiment and application in the late-stage modification of natural products and pharmaceutical derivatives showcased the synthetic potential of the direct denitrative N-arylation protocol in synthetic chemistry.

Automated summary

We have developed an efficient palladium-catalyzed denitrative N-arylation method, which enables the cross-coupling of N-H heteroarenes with nitroarenes. This method allows for the selective synthesis of various functionalized N-arylated heterocycles with moderate to excellent yields. Furthermore, its success in scale-up experiments and late-stage modification of natural products and pharmaceutical derivatives demonstrates the synthetic potential of this direct denitrative N-arylation protocol in synthetic chemistry.