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N-Alkylation of functionalized amines with alcohols using a copper-gold mixed photocatalytic system.

ABSTRACT: 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 situ prepared 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.

SUBMITTER: Wang LM

PROVIDER: S-EPMC5931965 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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N-Alkylation of functionalized amines with alcohols using a copper-gold mixed photocatalytic system.

Wang Lyu-Ming LM Morioka Yuna Y Jenkinson Kellie K Wheatley Andrew E H AEH Saito Susumu S Naka Hiroshi H

Scientific reports 20180502 1

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 temper ...[more]

PMID: 29720619

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