Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 5, Pages 901-907Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo01218a
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Funding
- Natural Science Foundation of Henan Province [202300410232]
- Henan Normal University [2019QK01]
- Start-Up Fund from Henan Normal University [5101039170194]
- China Postdoctoral Science Foundation [2020T130176]
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The reported reaction utilizes organic photoredox catalysis to achieve intermolecular pyridylation/phosphinoylation of alkenes, with broad substrate scope under mild metal-free conditions, suitable for gram-scale production and modification of medicinal molecules. Mechanistic investigations indicate that triethylamine functions as both single-electron transfer (SET) and hydrogen atom transfer (HAT) agents in the reaction.
Reported here is an intermolecular pyridylation/phosphinoylation of alkenes using 4-cyanopyridine and diphenylphosphine oxide under visible-light-induced organic photoredox catalysis. The reaction occurs under mild metal-free conditions, possessing a broad substrate scope. The protocol can be practiced on a gram scale and applied to the modification of natural product-derived and medicinally relevant complex molecules containing a styrene unit. Mechanistic investigations suggest that triethylamine serves as both single-electron transfer (SET) and hydrogen atom transfer (HAT) agents.
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