N-Alkylation of Functionalized Amines with Alcohols Using a Copper–Gold Mixed Photocatalytic System

Papers published
Lyu-Ming Wang , Yuna Morioka , Kellie Jenkinson , Andrew E. H. Wheatley , Susumu Saito, and Hiroshi Naka, Sci. Rep., 2018, 8, 6931. DOI: 10.1038/s41598-018-25293-z
  • Direct functionalization of amino groups in complex organic molecules is one of the most important key technologies in modern organic synthesis, especially in the synthesis of bio-active chemicals and pharmaceuticals. Whereas numerous chemical reactions of amines have been developed to date, a selective, practical method for functionalizing complex amines is still highly demanded. Here we report the first late-stage N-alkylation of pharmaceutically relevant amines with alcohols at ambient temperature. This reaction was achieved by devising a mixed heterogeneous photocatalyst in situprepared from Cu/TiO2 and Au/TiO2. The mixed photocatalytic system enabled the rapid N-alkylation of pharmaceutically relevant molecules, the selective mono- and di-alkylation of primary amines, and the non-symmetrical dialkylation of primary amines to hetero-substituted tertiary amines.

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