Photocatalytic para-Selective C-H Functionalization of Anilines with Diazomalonates
Ujjwal Karmakar1, Ho Seong Hwang1, Yunjeong Lee1
1Department of Chemistry, Chung-Ang University, 84 Heukseok-ro, Dongjak-gu, Seoul 06974, Republic of Korea.
Abstract:
Visible-light-induced para-selective C-H functionalization of anilines over N-H insertion was developed using diazomalonates with the help of an Ir(III) photocatalyst. The para-selective radical-radical cross coupling proceeded via C-centered radical intermediates generated from both anilines and diazomalonates. The photochemistry of anilines could be extended to other N-heterocycles, such as indole and carbazole. The reaction pathway for the selective C-C coupling was validated by electrochemical and photophysical experiments as well as computational studies.
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