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Synthesis of gem-Disulfonyl Enamines via an Iminyl-Radical-Mediated Formal 1,3-HAT/Radical Coupling Cascade.

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We herein report the first example of an iminyl-radical-mediated formal 1,3-HAT/radical coupling cascade of vinyl azides leading to the synthesis of tetrasubstituted gem-disulfonyl enamines. It is possible to employ a… Click to show full abstract

We herein report the first example of an iminyl-radical-mediated formal 1,3-HAT/radical coupling cascade of vinyl azides leading to the synthesis of tetrasubstituted gem-disulfonyl enamines. It is possible to employ a variety of vinyl azides and sulfinate salt coupling elements without sacrificing effectiveness and scalability. The combination of experimental studies and DFT calculations showed that this reaction proceeds via a radical addition/formal 1,3-HAT/radical coupling mechanism.

Keywords: mediated formal; iminyl radical; hat radical; radical coupling; radical mediated; formal hat

Journal Title: Organic letters
Year Published: 2022

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