Reductive amination/cyclization of levulinic acid to pyrrolidones versus pyrrolidines by switching the catalyst from AlCl₃ to RuCl₃ under mild conditions

Abstract

Reductive amination/cyclization of levulinic acid was presented to selectively produce pyrrolidones versus pyrrolidines by switching the catalyst from AlCl3 to RuCl3 under mild conditions.

A Multiphase Protocol for Selective Hydrogenation and Reductive Amination of Levulinic Acid with Integrated Catalyst Recovery

“…[31] Homogeneous and heterogeneousc atalysts (i.e.,A u/ZrO 2 , Pt-MoO x /TiO 2 ,C -coated Ni nanoparticles, Ir/SiO 2 -SO 3 H, and Ru-, Ir-, and In complexes) prove active for the reaction, by using either FA in at ransfer hydrogenation or H 2 or even hydrosilanes as reductants. [31][32][33][34][35][36][37][38] The poor catalyst/product separation and catalystr euse, however,a re serious drawbacks, especially for large-scale applications. [31] To cope with these problems, the present MP approach was explored for the modelr eaction of LA with cyclohexylamine.…”

Selective and Efficient Iridium Catalyst for the Reductive Amination of Levulinic Acid into Pyrrolidones

“…Indium, aluminum and boron-catalyzed reductive amination of levulinic acid using silanes as reducing agents were reported. [6,16] Very good results were obtained but these catalysts suffered from some drawbacks such as high catalyst loading, excess of silanes (waste issue), high temperature and necessity to use organic solvents. Finally, some catalyst-free procedures have been reported.…”

Reductive Amination/Cyclization of Methyl Levulinate with Aspartic Acid: Towards Renewable Polyesters with a Pendant Lactam Unit

“…Of the different possible pathways, reductive amination with primary amines and subsequent cyclization is one of the most attractive methods . Indeed, it gives access to value‐added N ‐substituted 5‐methyl‐pyrrolidone, which is a promising biosourced solvent, giving an alternative to the widely used toxic and carcinogenic N ‐methyl‐2‐pyrrolidone (NMP) . The synthesis involves the hydrogenation of a Schiff‐base intermediate to afford a secondary amine, which is subsequently converted to a lactam ring by an intramolecular cyclization.…”