Deconstructive Pyridylation of Unstrained Cyclic Amines through a One-Pot Umpolung Approach

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 C4functionalized pyridines under visible-light conditions in the absence of an external photocatalyst.

Automated summary

A one-pot umpolung method using N-amidopyridinium salts was developed for the ring-opening pyridylation of unstrained cyclic amines. This process involves the formation of electron donor-acceptor complexes between bromide and N-amidopyridinium salts, leading to the functionalization of pyridines. It provides a powerful synthon for preparing C4-functionalized pyridines under visible-light conditions in the absence of an external photocatalyst.