(560bv) A Metal- and Solvent-Free Synthesis of aminoalcohols under Continuous Flow Conditions

The use of multifunctional organocatalysts and continuous flow platform are commonplace in modern chemical transformation. Herein, we describe a method for immobilization of trifunctional organocatalysts on porous composite hollow fiber and demonstrate their application as heterogeneous catalyst and continuous-flow microfluidic reactor for chemical transformation. The polyamide imide hollow fibers (PAIHF’s) are functionalized with aminosilanes and bromine source to immobilize covalently hydrogen-bond donor groups (-OH and -NH), and nucleophilic [Br^−] species upon the fiber surface and provide trifunctional acid-base-nucleophilic organocatalysts and microfluidic reactors. The cooperative effects of Br/APS/PAIHF trifunctional organocatalysts are elucidated in the CO₂ cycloaddition and hydroxyalkylation of aniline under batch and continuous flow synthesis. Our results indicated that the synergistic cooperative effect of trifunctional organocatalyst on PAIHF leads to a maximum 1-(phenylamino)propan-2-ol selectivity of 97.1% at 60% aniline conversion and 0.02 cm³/min flow rate. While knowledge of the acid-base-nucleophilic trifunctional cooperativity is still limited, these findings demonstrate useful structure-property trends that can be used to design more efficient organocatalysts for sustainable chemical transformation.