Metallaphotoredox Deoxygenative Arylation of Alcohols: A Viable Strategy for the Synthesis of Tryptamine Derivatives

A metallaphotoredox deoxygenative arylation of alcohols strategy has been applied to prepare in a one pot procedure tryptamine derivatives. Starting from 3-Br indoles and 2-amino alcohols, in the presence of an Ir photocatalyst and catalytic amounts of NiBr2, 3-(2-aminoethyl)-substituted indoles have been synthesized in up to 76% yield after 2 h under blue LED irradiation. Improved productivity and space time yield were observed when continuous flow technologies were employed (60% yield with 30 min residence time).