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Diazo compounds as well as their precursors represent an interesting category for organic synthesis. Particularly N-tosylhydrazones, have attracted attention for their easy accessibility and diverse reactivity, including carbene transfer reactions. We described a visible light induced N-H insertion reaction of anilines on in-situ generated diazo compounds. Optimal conditions using DBU in toluene yielded desired products efficiently. Mechanistic studies enabled us to trap a carbene intermediate that has a key role in this transformation.
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Faure et al. (2024) studied this question.
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