Alkyl Radical Addition to Aliphatic and Aromatic N -Acylhydrazones Using an Organic Photoredox Catalyst

Stephen T J Cullen; Gregory K Friestad

doi:10.1021/acs.orglett.9b03053

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Alkyl Radical Addition to Aliphatic and Aromatic N -Acylhydrazones Using an Organic Photoredox Catalyst

Journal article

Peer reviewed

Alkyl Radical Addition to Aliphatic and Aromatic N -Acylhydrazones Using an Organic Photoredox Catalyst

Stephen T J Cullen and Gregory K Friestad

Organic letters, Vol.21(20), pp.8290-8294

10/18/2019

DOI: 10.1021/acs.orglett.9b03053

PMCID: PMC6900872

PMID: 31560554

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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 -acylhydrazones in the presence of MgCl . With -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.

Details

Title: Subtitle: Alkyl Radical Addition to Aliphatic and Aromatic N -Acylhydrazones Using an Organic Photoredox Catalyst
Creators: Stephen T J Cullen - Department of Chemistry , University of Iowa , Iowa City , Iowa 52242 , United States
Gregory K Friestad - Department of Chemistry , University of Iowa , Iowa City , Iowa 52242 , United States
Resource Type: Journal article
Publication Details: Organic letters, Vol.21(20), pp.8290-8294
DOI: 10.1021/acs.orglett.9b03053
PMID: 31560554
PMCID: PMC6900872
NLM abbreviation: Org Lett
ISSN: 1523-7060
eISSN: 1523-7052
Grant note: T32 GM067795 / NIGMS NIH HHS
Language: English
Date published: 10/18/2019
Academic Unit: Chemistry
Record Identifier: 9984216616802771

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