Photocatalytic synthesis of CF3-containing β-amino alcohols via covalent metal-organic frameworks

Abstract The construction of CF3-containing β-amino alcohols represents a promising approach for drug discovery due to their enhanced metabolic stability and tunable pharmacological properties. However, the development of non-noble metal heterogeneous photocatalysts for the efficient one-step synthesis of trifluoromethyl (CF3)-containing β-amino alcohol motifs under mild conditions poses significant challenges. In this work, we successfully synthesized two photoactive covalent metal-organic frameworks (CMOFs) capable of photocatalyzing the one-step conversion of allylamines to CF3-containing β-amino alcohols via trifluoromethylation and photo-oxidation. Notably, the catalytic reaction can be performed under continuous-flow conditions, reducing the reaction time from 12 hours to 50 minutes while achieving a product yield of 6.2 grams of CF3-containing β-amino alcohol. Additionally, under CO2 atmosphere, CF3-containing oxazolidinones can be efficiently obtained through oxytrifluoromethylation of alkenes. Both catalytic reactions demonstrate high yields under natural sunlight illumination, further highlighting the practicality and sustainability of this approach.