Open AccessAlkyl Radical Addition to Aliphatic and Aromatic N-Acylhydrazones Using an Organic Photoredox Catalyst
Author(s) -
Stephen T. J. Cullen,
Gregory K. Friestad
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b03053
Subject(s) - chemistry , photoredox catalysis , catalysis , alkyl , intermolecular force , photocatalysis , radical , adduct , hydrazine (antidepressant) , primary (astronomy) , organic chemistry , bond cleavage , amine gas treating , combinatorial chemistry , photochemistry , molecule , physics , chromatography , astronomy
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 MgCl 2 . 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.