Regioselective Electrooxidative [3+2] Annulation between Indole and Aniline Derivatives to Construct Functionalized
Qing-Hong Huang1, Shuai-Xin Li1, Jun-Chen Kang1
1Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs and School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China.
Abstract:
A protocol for the electrooxidative [3+2] annulation to generate indolo[2,3-b]indoles in an undivided cell is reported. It exhibits good yields with excellent regioselectivities and tolerates various functional groups without external chemical oxidants. Cyclic voltammetry and density functional theory calculations indicate that the [3+2] annulation is initiated by the simultaneous anodic oxidation of indole and aniline derivatives, and the step to determine the rate relies on the combination of radical cations.
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