Tosylazide as N1-Synthon: Iron-Catalyzed Nitrogenative Dimerization of Indoles 
to p-Bisindolopyrazine Derivatives

Li, Jianan; Sun, Xiaohan; Dmitrieva, Evgenia; Israel, Noel; Wu, Fupeng; Yang, Lin; Liu, Renxiang; Feng, Xinliang; Plietker, Bernd

doi:10.1021/acs.orglett.3c04209

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Tosylazide as N1-Synthon: Iron-Catalyzed Nitrogenative Dimerization of Indoles to p-Bisindolopyrazine Derivatives

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Wu, Fupeng
Department of Synthetic Materials and Functional Devices (SMFD), Max Planck Institute of Microstructure Physics, Max Planck Society;

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Feng, Xinliang
Department of Synthetic Materials and Functional Devices (SMFD), Max Planck Institute of Microstructure Physics, Max Planck Society;

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https://doi.org/10.1021/acs.orglett.3c04209
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Citation

Li, J., Sun, X., Dmitrieva, E., Israel, N., Wu, F., Yang, L., et al. (2024). Tosylazide as N1-Synthon: Iron-Catalyzed Nitrogenative Dimerization of Indoles to p-Bisindolopyrazine Derivatives. Organic Letters, 26(5), 1046-1050. doi:10.1021/acs.orglett.3c04209.

Cite as: https://hdl.handle.net/21.11116/0000-000E-79DF-0

Abstract

We present a straightforward one-step process to access a range of novel p-diindolepyrazines via an unprecedented [n-Bu₄N][Fe(CO)₃(NO)] (TBA[Fe])-catalyzed intermolecular nitrogenative dimerization of various indole derivatives. Remarkably, tosylazide functions as a N1-synthon forming the central pyrazine unit that joins the two indole subunits. The catalytic transformation shows a good substrate scope, and the obtained products show interesting electronic properties.