Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis

The synthesis of anilines and indoles from cyclohexanones using a Pd/C-ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.

Automated summary

The synthesis of anilines and indoles from cyclohexanones using a Pd/C-ethylene system was successfully achieved under nonaerobic conditions with a simple combination of NH4OAc and K2CO3. The desired products were generated through hydrogen transfer between cyclohexanone and ethylene, with the reaction tolerating a variety of substitutions on the starting cyclohexanones.