The CN shuffle: The described intramolecular alkenyl- and acylcyanation reaction of activated alkenes proceed by cleavage of a CN bond. This protocol provides access to functionalized acyclic nitriles with quaternary carbon centers under neutral and mild reaction conditions, demonstrates broad scope, and good functional-group compatibility and versatility. Y=O or CHR4; R1,R4=electron-withdrawing group; TBACN=tetrabutylammonium cyanide.
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