Hydroxylamine-Mediated C–C Amination via an Aza-Hock Rearrangement

Stephen Hashmi reports on the hydroxylamine-mediated C–C amination via an aza-Hock rearrangement.

Anilines are precursors to many industrial chemicals, including dyes, resins, perfumes, pigments, herbicides, fungicides, agrochemicals, pharmaceuticals, explosives, various polymers such as polyurethanes and rubber chemicals. “For this reason,” according to Professor A. Stephen K. Hashmi from Heidelberg University (Germany), “aniline synthesis is a common task for many chemists but is always accompanied by chemoselectivity issues using both traditional nitration–reduction or modern arene C–H amination. However, C–C amination is an alternative way to address such site-selectivity issues. A few methods have been reported for harnessing this strategy to afford the desired anilines, albeit with hazardous reagents or harsh conditions: decarboxylative amination, Beckmann rearrangement, and Schmidt-like rearrangement are among these methods. Therefore, new strategies for aniline synthesis via C–C amination in mild conditions are needed urgently.”

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