Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine

In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed C sp 2 -P and C sp 3 -P bond formations were efficiently achieved by reacting aryl/alkyl...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-07, Vol.19 (26), p.595-5911
Main Authors: Koohgard, Mehdi, Hosseini-Sarvari, Mona
Format: Article
Language:English
Subjects:
Functional groups
Oxidants
Oxidizing agents
Phosphonates
Zinc
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Summary:In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed C sp 2 -P and C sp 3 -P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups. A set of zinc phthalocyanine-catalyzed phosphonylations of alkyl/arylhydrazines with trialkylphosphites under visible light was developed. The reactions proceeded in the presence of atmospheric oxygen without using any additional ligand and/or base.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob00848j