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Visible-Light-Driven Aryl Migration and Cyclization of α-Azido Amides.

Siyu LiangKaijie WeiYajun LinTuming LiuDian WeiBing HanWei Yu
Published in: Organic letters (2021)
This paper reports two new visible-light-promoted radical reactions of α-azido amides. By catalysis of [Ir(ppy)2(dtbbpy)]PF6 with i-Pr2NEt as the reducing agent, N-aryl α-azido tertiary amides were first converted to the corresponding aminyl radicals through reduction of the azido group; the aminyl radicals then underwent N-to-N aryl migration to give α-anilinyl-functionalized amides. α-Azido secondary amides, on the other hand, reacted with the solvent ethanol and i-Pr2NEt to afford the imidazolinone products.
Keyphrases
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