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![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Alkyl Radical Addition to Aliphatic and Aromatic N-Acylhydrazones Using an Organic Photoredox Catalyst
Stephen T J Cullen1, Gregory K Friestad1
1Department of Chemistry , University of Iowa , Iowa City , Iowa 52242 , United States.
Abstract:
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.
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