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Iridium-catalyzed Synthesis of Saturated N‑Heterocycles from Aldehydes and SnAP Reagents with Continuous Flow Photochemistry

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journal contribution
posted on 20.03.2018, 17:48 by Chalupat Jindakun, Sheng-Ying Hsieh, Jeffrey W. Bode
Commercially available tin amine protocol (SnAP) reagents provide a simple approach to the synthesis of a wide variety of saturated N-heterocycles from aldehydes. In this report, we disclose that the copper­(II) promoter and hexafluoroisopropanol can be replaced by photocatalytic conditions using Ir­[dF­(CF3)­ppy]2(dtbbpy)­PF6 in CH3CN. Continuous flow photochemical conditions provide a clean, scalable approach to valuable products including morpholines, piperazines, thiomorpholines, diazepanes, and oxazepanes from aldehyde starting materials.