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Updated: Jun 10, 2025

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TCCA/RSeSeR-Mediated Selenoalkoxy of Allenamides via a Radical Process: Synthesis of Selanyl-allylic N,O-Aminals
Qingsong Liu1, Jiri Gele1, Kun Zhao1
1Key Laboratory of Basic Chemistry of the State Ethnic Commission, School of Chemistry and Environment, Southwest Minzu University, Chengdu 610041, P. R. China.
Abstract:
An efficient TCCA (trichloroisocyanuric acid)/RSeSeR-mediated selenoalkoxy of allenamides for the construction of selanyl-allylic N,OA-aminal derivatives was developed. The reaction exhibits good functional group tolerance and high efficiency, affording the products in good to excellent yields. Mechanistic investigations indicated that a selanyl-allylic radical intermediate was first formed via the RSe radical added to the central carbon of allenamides, which subsequently furnished highly stable selanyl-allylic carbocation intermediate by abstraction of an electron by the chlorine radical. Moreover, this is the first report of using selenium reagent (RSeCl) to activate allenamides via a radical process.
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