Diazo compounds and their precursors represent an interesting chemical 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 efficiently yielded the desired products. Mechanistic studies enabled us to trap a carbene intermediate that plays a key role in the transformation.
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Faure et al. (2024) studied this question.
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