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. Author manuscript; available in PMC: 2023 Apr 29.
Published in final edited form as: Science. 2022 Apr 28;376(6592):527–532. doi: 10.1126/science.abo4282

Fig. 3. Scope of the photochemical conversion of azaarene N-oxides into acylazoles.

Fig. 3.

Conditions: 1 (0.3 mmol), toluene (0.06 M), 390-nm LED, 0.5 to 5 hours at 25°C, then TFA (0.3 mmol) for 2 to 5 hours at 25°C. Isolated yields are given. The asterisk symbol indicates where acidolysis was conducted with TsOH•H2O instead of TFA. The single-dagger symbol indicates where acidolysis was conducted at 60°C. The double-dagger symbol indicates where, instead of acidolysis, photolysate was concentrated and refluxed in H2O/MeOH (1:1). Hg lamp yields measured by proton nuclear magnetic resonance versus an internal standard. Ph, phenyl group; OMe, methoxy group; MTO, methyl-trioxorhenium; BMIDA, N-methyliminodiacetyl boronate; Boc, butoxycarbonyl; nPr, n-propyl; TsOH, para-toluenesulfonic acid; (BzO)2, benzoyl peroxide; tBu, tert-butyl.