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Under mild dual photoredox/copper catalysis, the reaction of N-alkoxypyridinium salts with readily available silyl reagents (TMSN3, TMSCN, TMSNCS) afforded d-azido, d-cyano, and d-thiocyanato alcohols in high yields. The reaction went through a domino process involving alkoxy radical generation, 1,5-hydrogen atom transfer (1,5-HAT) and copper-catalyzed functionalization of the resulting C-centered radical. Conditions for catalytic enantioselective d-C(sp3)@H cyanation were also documented.
Jeremy Luterbacher, Songlan Sun, Stefania Bertella, Anastasiia Komarova
Jeremy Luterbacher, Songlan Sun, Stefania Bertella, Anastasiia Komarova