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. 2025 Aug 5.
doi: 10.1007/s11030-025-11279-3. Online ahead of print.

Construction of multifunctionalized (oxo)indoles via O-Selective interception of the zwitterionic intermediate with N=O

Bao-Fan Wang  1   2 , Ziming Qiu  1 , Fei Lian  2 , Mengke Zhang  2 , Tai-Chen Liu  2 , Zheng-Hui Kang  3 , Jiu-Ling Li  4
Affiliations

Construction of multifunctionalized (oxo)indoles via O-Selective interception of the zwitterionic intermediate with N=O

Bao-Fan Wang et al. Mol Divers. .

Abstract

A straightforward multi-component method is developed to construct multifunctionalized (oxo)indoles under Pd(II) catalysis via intramolecular or intermolecular reaction pathways between electron-rich arenes, diazo compounds, and nitrosoarenes. Under the catalysis of palladium, metal carbene, generated from diazo compound, reacts with electron-rich arene to form zwitterionic intermediate, which is trapped by activated nitrosobenzene to give the desired product. It is worth noting that indole and nitrosobenzene have a competitive relationship and react with diazo compounds to produce different two-component products. Therefore, in multi-component reactions of diazo compounds, electron-rich arene, and nitrosobenzene, obtaining a single multifunctional indole product with high chemical selectivity remains a visible challenge.

Keywords: High chemical selectivity; Metal carbene; Multi-component reactions; Multifunctionalized (oxo)indoles.

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Conflict of interest statement

Declarations. Conflict of interest: The authors declare no competing interests.

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