Figure 3.

C–C and C–N coupling via decarboxylative protocols. (a) The reaction between N-Boc-proline with 1-bromo-4-(trifluoromethyl)-benzene was evaluated with a variety of light sources using standard conditions; superior results were obtained with the 427 nm LEDs (see Supporting Information). (b) A range of results have been obtained for several conditions, with high, moderate, or low yield being replicated between the FLOSIM device and the commercial flow setup (see Supporting Information). (c) The reaction was successfully scaled using a Vapourtec E-Series with a 10 mL reactor coil (1.3 mm ID). (d) Reaction between activated carboxylic acid iodonium salts and 3-chloro-indazole as the N-nucleophile via dual-photoredox copper catalysis. Superior results were obtained with a 390 nm Kessil LED light source. (e) A range of results have been obtained for several conditions, with high, moderate, or low yield being replicated between the FLOSIM device and the commercial flow setup (see Supporting Information). (f) The reaction was successfully scaled at a 40 mmol level affording 7.6 g of the desired product (69% yield) using a Vapourtec E-Series with a 10 mL reactor coil (1.3 mm ID). PC corresponds to 4CzIPN.