Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction

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Abstract

An unforeseen twist in a seemingly trivial Bischler-Napieralski reaction led to the selective formation of an unexpected carbazole product. The reaction proved to be general, providing access to a range of diversely substituted carbazoles from readily available substrates. Judicious variation of substituents revealed a complex cascade mechanism comprising no less than 10 elementary steps, that could be diverted in multiple ways toward various other carbazole derivatives.

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Faltracco, M., Ortega-Rosales, S., Janssen, E., Cioc, R. C., Vande Velde, C. M. L., & Ruijter, E. (2021). Synthesis of Carbazoles by a Diverted Bischler-Napieralski Cascade Reaction. Organic Letters, 23(8), 3100–3104. https://doi.org/10.1021/acs.orglett.1c00785

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