Manufacturing valuable N-containing chemicals from biomass is highly desirable yet challenging. Herein, a novel strategy was developed for efficient production of 2-(1-hydroxyethyl)-imidazoline (HI), a high-value and versatile building block for synthesizing a myriad of bioactive targets, directly from carbohydrates under mild reaction conditions. With this strategy, bio-based HI was produced from fructose in one step with as high as 77 C % isolated yield in the presence of ethylenediamine (EDA) and InCl3 at 130 °C. The synergistic functions of EDA and InCl3 were identified for the transformation, wherein EDA promoted the scission of C-C bond of fructose backbone via retro-aldol (R-A) reaction and rapidly trapped in-situ formed reactive carbonyl-containing C3 intermediate for HI formation to avoid undesired side reaction, and InCl3 facilitated the formation of this C3 intermediate and the final 1,2-hydrid shift step.
Keywords: 2-(1-hydroxyethyl)-imidazoline; biomass valorization; carbohydrates; fructose; homogeneous catalysis.
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