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Direct and Practical Synthesis of Primary Anilines through Iron-Catalyzed C–H Bond Amination

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Legnani,  Luca
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Prina Cerai,  Gabriele
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Morandi,  Bill
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Legnani, L., Prina Cerai, G., & Morandi, B. (2016). Direct and Practical Synthesis of Primary Anilines through Iron-Catalyzed C–H Bond Amination. ACS Catalysis, 6(12), 8162-8165. doi:10.1021/acscatal.6b02576.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002C-A1BE-9
Abstract
The direct C–H amination of arenes is an important strategy to streamline the discovery and preparation of functional molecules. Herein, we report an operationally simple arene C–H amination reaction that, in contrast to most literature precedent, affords directly the synthetically versatile primary aniline products without relying on protecting group manipulations. Inexpensive Fe(II)-sulfate serves as a convenient catalyst for the transformation. The reaction tolerates a wide scope of arenes, including structurally complex drugs. Importantly, the arene substrates are used as limiting reagents in the transformation. This operationally simple transformation should considerably accelerate the discovery of medicines and functional molecules.