Increased versatility of intermolecular radical addition to imino acceptors via photoredox catalysis is reported. Primary and secondary radicals, generated via visible-light photocatalysis from alkyl biscatecholatosilicates with organocatalyst 4CzIPN, add successfully to both aromatic and aliphatic N-acylhydrazones in the presence of MgCl2. With N-benzoylhydrazones, a simple reductive cleavage of the N-N bond of the hydrazine adduct furnishes the free amine. Synthetic utility is exemplified in a synthetic application toward repaglinide, a clinically important hypoglycemic agent.
Increased versatility of intermolecular radical addition to imino acceptors via photoredox catalysis is reported. Primary and secondary radicals, generated via visible-light photocatalysis from alkyl biscatecholatosilicates with n class="Chemical">organocatalyst 4CzIPN, add successfully to both aromatic and aliphatic N-acylhydrazones in the presence of MgCl2. With N-benzoylhydrazones, a simple reductive cleavage of the N-N bond of the hydrazine adduct furnishes the free amine. Synthetic utility is exemplified in a synthetic application toward repaglinide, a clinically important hypoglycemic agent.
Authors: Katherine C Forbes; Anne Marie Crooke; Yuri Lee; Masamu Kawada; Kian M Shamskhou; Rachel A Zhang; Jeffrey S Cannon Journal: J Org Chem Date: 2022-02-08 Impact factor: 4.354