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Synthesis 2021; 53(06): 1003-1022
DOI: 10.1055/s-0040-1705978
DOI: 10.1055/s-0040-1705978
review
Shining Light on the Light-Bearing Element: A Brief Review of Photomediated C–H Phosphorylation Reactions
We thank the Canada Research Chairs Foundation, the Canada Foundation for Innovation (CFI), the Fonds Québécois de la Recherche sur la Nature et les Technologies (FQRNT) Center for Green Chemistry and Catalysis, the Natural Sciences and Engineering Research Council of Canada (NSERC) and McGill University for financial support.
Abstract
Organophosphorus compounds have numerous useful applications, from versatile ligands and nucleophiles in the case of trivalent organophosphorus species to therapeutics, agrochemicals and material additives for pentavalent species. Although phosphorus chemistry is a fairly mature field, the construction of C–P(V) bonds relies heavily on either prefunctionalized substrates such as alkyl or aryl halides, or requires previously oxidized bonds such as C=N or C=O, leading to potential sustainability issues when looking at the overall synthetic route. In light of the recent advances in photochemistry, using photons as a reagent can provide better alternatives for phosphorylations by unlocking radical mechanisms and providing interesting redox pathways. This review will showcase the different photomediated phosphorylation procedures available for converting C–H bonds into C–P(V) bonds.
1 Introduction
1.1 Organophosphorus Compounds
1.2 Phosphorylation: Construction of C–P(V) Bonds
1.3 Photochemistry as an Alternative to Classical Phosphorylations
2 Ionic Mechanisms Involving Nucleophilic Additions
3 Mechanisms Involving Radical Intermediates
3.1 Mechanisms Involving Reactive Carbon Radicals
3.2 Mechanisms Involving Phosphorus Radicals
3.2.1 Photoredox: Direct Creation of Phosphorus Radicals
3.2.2 Photoredox: Indirect Creation of Phosphorus Radicals
3.2.3 Dual Catalysis
3.3 Photolytic Cleavage
4 Conclusion and Outlook
Key words
photocatalysis - photoredox - phosphorylation - organophosphorus compounds - phosphorus chemistryPublication History
Received: 29 September 2020
Accepted after revision: 24 October 2020
Article published online:
23 November 2020
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