Palladium-catalyzed N-arylation of (hetero)aryl chlorides with pyrroles and their analogues
Ying Yin1, Yuxuan Xiao1, Xun Yang1
1School of Chemistry and Chemical Engineering, Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Guangxi University, Nanning 530004, Guangxi, P. R. China. linyu@gxu.edu.cn.
Abstract:
We present a mild and efficient method for the arylation of N-H heteroarenes using a low-loading Pd/keYPhos catalyst (0.8 mol%). This approach employs inexpensive and structurally diverse aryl chlorides as electrophiles in reactions with indoles, pyrroles, and carbazole, enabling the construction of a wide range of N-arylated products. The method exhibits excellent functional group tolerance and is suitable for gram-scale synthesis. Furthermore, the relatively inert Ar-Cl bond allows for late-stage functionalization of pharmaceuticals and stepwise coupling reactions, providing a complementary strategy for the N-arylation of N-H heteroarenes.
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