Metallaphotocatalytic triple couplings for modular synthesis of elaborate N-trifluoroalkyl anilines

Ting Zhou, Zhong-Wei Zhang, Jing Nie, Fuk Yee Kwong, Jun-An Ma () and Chi Wai Cheung ()
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Ting Zhou: Tianjin University
Zhong-Wei Zhang: Tianjin University
Jing Nie: Tianjin University
Fuk Yee Kwong: New Territories
Jun-An Ma: Tianjin University
Chi Wai Cheung: Tianjin University

Nature Communications, 2024, vol. 15, issue 1, 1-13

Abstract: Abstract The integration of trifluoromethyl groups and three-dimensional quaternary carbon moieties into organic molecules has emerged as a prominent strategy in medicinal chemistry to augment drug efficacy. Although trifluoromethyl (hetero)aromatic amines and derivatives are prevalent frameworks in pharmaceuticals, the development of trifluoromethyl-embedded, intricately structured alkyl amine scaffolds for medicinal research remains a significant challenge. Herein, we present a metallaphotoredox multicomponent amination strategy employing 3,3,3-trifluoropropene, nitroarenes, tertiary alkylamines, and carboxylic acids. This synthetic pathway offers notable advantages, including the accessibility and cost-effectiveness of starting materials, high levels of chemo- and regioselectivity, and modularity. Furthermore, this approach enables the synthesis of a broad spectrum of aniline compounds featuring both trifluoromethyl group and distal quaternary carbon motifs along the aliphatic chains. The accelerated access to such elaborate N-trifluoroalkyl anilines likely involves three sequential radical-mediated coupling events, providing insightful implications for the retrosynthesis of potential compounds in organic synthesis and drug discovery.

Date: 2024
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DOI: 10.1038/s41467-024-53828-8

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