C(sp³)–H functionalisation of N-aryl tetrahydroisoquinolines via an iron-catalysed aerobic nitro-Mannich reaction and continuous flow processing

• Martin Brzozowski
• Jose A. Forni
• G. Paul Savage and Anastasios Polyzos^*

• CSIRO Manufacturing Flagship, Bayview Avenue, Clayton, Australia

An efficient nitro-Mannich type direct α-C(sp³)–H functionalisation of N-aryl-1,2,3,4-tetrahydroisoquinolines catalysed by simple iron salts in combination with O₂ as the terminal oxidant is described. The use of a Teflon AF-2400 membrane Tube-in-Tube reactor under continuous flow conditions allowed for considerable process intensification to be achieved relative to previous batch methods.

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