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

Fe(TF4DMAP)Cl-catalysed intramolecular C–H amination of N-containing alkyl azides under photocatalytic conditionsa.

graphic file with name d0sc00784f-u6.jpg
Entry Substrate Product Yield (%)
1 graphic file with name d0sc00784f-u7.jpg graphic file with name d0sc00784f-u8.jpg 75
2 graphic file with name d0sc00784f-u9.jpg graphic file with name d0sc00784f-u10.jpg 70
3 graphic file with name d0sc00784f-u11.jpg graphic file with name d0sc00784f-u12.jpg 78
4 graphic file with name d0sc00784f-u13.jpg graphic file with name d0sc00784f-u14.jpg 61; 30b
5 graphic file with name d0sc00784f-u15.jpg graphic file with name d0sc00784f-u16.jpg 45
6 graphic file with name d0sc00784f-u17.jpg graphic file with name d0sc00784f-u18.jpg 98
7 graphic file with name d0sc00784f-u19.jpg graphic file with name d0sc00784f-u20.jpg 95
8 graphic file with name d0sc00784f-u21.jpg graphic file with name d0sc00784f-u22.jpg 55
a

Reactions were run under argon with 0.3 mmol of the azide, Boc2O (0.36 mmol), 3 × 10−3 mmol of the catalyst (1 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.

b

[Fe(F20TPP)Cl] was used as the catalyst. Yields were determined by 1H NMR spectroscopy.