Deconstructive Pyridylation of Unstrained Cyclic Amines through a One-Pot Umpolung Approach
Seonghyeok Hong, Seonghyeok Hong, Byeongseok Kweon, Wooseok Lee, Sukbok Chang, Sungwoo Hong, Sungwoo Hong
Abstract
A one-pot umpolung method for the ring-opening pyridylation of unstrained cyclic amines was developed using N -amidopyridinium salts. This process involves the formation of electron donor–acceptor complexes between bromide and N -amidopyridinium salts, ultimately leading to the functionalization of pyridines. This protocol is compatible with a range of 5- or 6-membered cyclic amines and pyridines, thereby providing a powerful synthon for preparing C4-functionalized pyridines under visible-light conditions in the absence of an external photocatalyst.
Topics & Concepts
UmpolungSynthonChemistrySurface modificationBromideRing (chemistry)Combinatorial chemistryPhotocatalysisCyclic aminesOrganic chemistryAmine gas treatingCatalysisNucleophilePhysical chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques