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. Author manuscript; available in PMC: 2024 Nov 1.
Published in final edited form as: Nature. 2023 Nov 1;623(7985):77–82. doi: 10.1038/s41586-023-06613-4

Fig. 2 |. Scope of the C-to-N transmutation of azaarenes.

Fig. 2 |

Conditions: 1 (0.3 mmol), toluene (0.06 M), 390 nm LED, 1–5 h at 25 °C, then ammonium carbamate (7.0 equivalents (equiv.)), pyridine (10.0 equiv.), O3/O2 bubbling for 5–20 min at −78 °C, followed by heating at 90 °C for 24 h. Isolated yields are given. aHeating for 48 h. b12.0 equiv. of ammonium carbamate. cAmmoniolysis was carried out with 12.0 equiv. of ammonium acetate in ethanol (0.1 M). dIsolated with alternative workup procedure. See Supplementary Information for the details. Ph, phenyl group; OMe, methoxy group; OEt, ethoxy group; mCPBA, meta-chloroperoxybenzoic acid; Tf, triflate; Cp*, 1,2,3,4,5-pentamethylcyclopentadiene; Boc, tert-butyloxycarbonyl.