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. 2020 Apr 17;11(18):4680–4686. doi: 10.1039/d0sc00784f

Fe(TF4DMAP)Cl-catalysed intramolecular C–H amination of α-azidoketones under photocatalytic conditionsa.

graphic file with name d0sc00784f-u23.jpg
Entry Substrate Product Conv. (%) Yield (%)
1 graphic file with name d0sc00784f-u24.jpg graphic file with name d0sc00784f-u25.jpg 70 46 (42)
2 graphic file with name d0sc00784f-u26.jpg graphic file with name d0sc00784f-u27.jpg 100 90 (80)
3 graphic file with name d0sc00784f-u28.jpg graphic file with name d0sc00784f-u29.jpg 100 92 (85)
4 graphic file with name d0sc00784f-u30.jpg graphic file with name d0sc00784f-u31.jpg 100 82 (77)
5 graphic file with name d0sc00784f-u32.jpg graphic file with name d0sc00784f-u33.jpg 100 84 (77)
6 graphic file with name d0sc00784f-u34.jpg graphic file with name d0sc00784f-u35.jpg 100 90 (82)
a

Reactions were run under argon with 0.3 mmol of the azide, Boc2O (0.36 mmol), 9 × 10−3 mmol of the catalyst (3 mol% with respect to the azide) and 120 mg 4 Å MS in 2.0 mL of anhydrous DCE in a 10.0 mL sealed tube. The tube was irradiated with a blue LED at 25–35 °C. Isolated yields are shown in the brackets.