ACS Catalysis
ACS Catalysis
4 years ago

Lactate-Based Ionic Liquid Catalyzed Reductive Amination/Cyclization of Keto Acids under Mild Conditions: A Metal-Free Route To Synthesize Lactams

Lactate-Based Ionic Liquid Catalyzed Reductive Amination/Cyclization of Keto Acids under Mild Conditions: A Metal-Free Route To Synthesize Lactams
Shien Guo, Zhengang Ke, Cailing Wu, Zhimin Liu, Hongye Zhang, Yu Chen, Bo Yu
Task-specific ionic liquids (ILs) have shown promising applications in catalysis. Herein we present lactate-based IL (e.g., 1-butyl-3-methylimidazolium lactate, [BMIm][Lac]) catalyzed reductive amination/cyclization of keto acids using triethoxysilane as a reducing agent, which provides a metal-free route to synthesis of lactams under mild conditions, even at room temperature. [BMIm][Lac] combined with (EtO)3SiH afforded a series of five- and six-membered lactams in good to excellent yields at 80 °C within 1 h, showing comparable performance to the best metal-based catalyst reported to date. The mechanism investigation indicated that the ILs (e.g., [BMIm][Lac]) served as a multifunctional catalyst, which could activate hydrosilanes and simultaneously catalyzed the cyclization of LA with amines.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b02231

DOI: 10.1021/acscatal.7b02231

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