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. Author manuscript; available in PMC: 2024 Sep 29.
Published in final edited form as: Science. 2023 Sep 28;381(6665):1474–1479. doi: 10.1126/science.adj5331

Fig. 3. Scope and selectivity.

Fig. 3.

(A) Scope of the reaction. Standard conditions: (i) 0.3 mmol aryl azide, 0.3 mmol ethylaminoethanol, 3 ml MeCN, and 427-nm light-emitting diode (LED); (ii) 0.3 mmol DBU, 3 ml dioxane heated to 80°C, and 0.6 mmol N-bromocaprolactam added dropwise at 80°C. Isolated yield of pyridine from aryl azide (black). Proton NMR (1H-NMR) yield of photolysis (blue) and interpolated yield of pyridine based on azepine yield (purple), shown in parentheses. Asterisk indicates NMR yield. (B) Demonstration that nonsymmetric substrates form only one pyridine isomer.