Regioselective α-Cyanation of Unprotected Alicyclic Amines
Fuchao Yu, Daniel A. Valles, Weijie Chen, Scott D. Daniel, Ion Ghiviriga, Daniel Seidel
Abstract
Secondary alicyclic amines are converted to α-aminonitriles via addition of TMSCN to their corresponding imines, intermediates that are produced in situ via the oxidation of amine-derived lithium amides with simple ketone oxidants. Amines with an existing α-substituent undergo regioselective α'-cyanation even if the C-H bonds at that site are less activated. Amine α-arylation can be combined with α'-cyanation to generate difunctionalized products in a single operation.
Topics & Concepts
CyanationAlicyclic compoundRegioselectivityChemistryCombinatorial chemistryOrganic chemistryCatalysisCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSynthesis and Catalytic Reactions