Alkyl Radical Addition to Aliphatic and Aromatic N-Acylhydrazones Using an Organic Photoredox Catalyst
Тип публикации: Journal Article
Дата публикации: 2019-09-27
scimago Q1
wos Q1
БС1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
31560554
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Краткое описание
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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ГОСТ
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Cullen S. T. J., Friestad G. K. Alkyl Radical Addition to Aliphatic and Aromatic N-Acylhydrazones Using an Organic Photoredox Catalyst // Organic Letters. 2019. Vol. 21. No. 20. pp. 8290-8294.
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Cullen S. T. J., Friestad G. K. Alkyl Radical Addition to Aliphatic and Aromatic N-Acylhydrazones Using an Organic Photoredox Catalyst // Organic Letters. 2019. Vol. 21. No. 20. pp. 8290-8294.
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TY - JOUR
DO - 10.1021/acs.orglett.9b03053
UR - https://doi.org/10.1021/acs.orglett.9b03053
TI - Alkyl Radical Addition to Aliphatic and Aromatic N-Acylhydrazones Using an Organic Photoredox Catalyst
T2 - Organic Letters
AU - Cullen, Stephen T J
AU - Friestad, Gregory K.
PY - 2019
DA - 2019/09/27
PB - American Chemical Society (ACS)
SP - 8290-8294
IS - 20
VL - 21
PMID - 31560554
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2019_Cullen,
author = {Stephen T J Cullen and Gregory K. Friestad},
title = {Alkyl Radical Addition to Aliphatic and Aromatic N-Acylhydrazones Using an Organic Photoredox Catalyst},
journal = {Organic Letters},
year = {2019},
volume = {21},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.orglett.9b03053},
number = {20},
pages = {8290--8294},
doi = {10.1021/acs.orglett.9b03053}
}
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MLA
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Cullen, Stephen T. J., and Gregory K. Friestad. “Alkyl Radical Addition to Aliphatic and Aromatic N-Acylhydrazones Using an Organic Photoredox Catalyst.” Organic Letters, vol. 21, no. 20, Sep. 2019, pp. 8290-8294. https://doi.org/10.1021/acs.orglett.9b03053.