Herein, 2‐(3‐acetyl‐3‐methyl‐1‐triazen‐1‐yl)benzoic acids are synthesized from anthranilic acids, including two new derivatives, without the use of strong bases. These compounds allow the slow and controlled generation of arynes via a white light‐induced process, which participates in 3 + 2 and 4 + 2 cycloaddition reactions, as well as in a metal‐free CN bond formation reaction. This chemistry, which tolerates sulfur‐, boron‐, and silicon‐containing compounds, is successfully performed on a scale of up to 1.5 mmol. A radical mechanism for the photogeneration of arynes is proposed based on a control reaction using TEMPO. In addition, the application of triazenylbenzoic acids is evaluated through the synthesis of a dehydroaporphine compound, which is an advanced synthetic intermediate for the synthesis of aporphine alkaloids.
Souza et al. (Sun,) studied this question.
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