Efficient reductive amination of 5-hydroxymethylfurfural by iridium-catalysed transfer hydrogenation

Abstract

Transfer hydrogenative reductive amination of 5-(hydroxymethy)furfural (HMF) has been accomplished, catalysed by a cyclometalated iridium catalyst with formic acid as a hydrogen source. The catalytic system afforded a TON of 9600 and TOF of 14 400 h⁻¹, and the reaction can be successfully scaled up to a 10 gram scale at a substrate-to-catalyst ratio of 10 000. A wide range of amines could be coupled with HMF to afford furan derived products, including modified drug molecules, key intermediates for drug synthesis and potential monomers for polymer synthesis.