Visible-light-induced bifunctionalisation of (homo)propargylic amines with CO2 and arylsulfinates

An unprecedented carboxylative sulfonylation of (homo)propargyl amines with CO2 and sodium arylsulfinates under visible light irradiation has been developed with high efficiency. This ruthenium-catalysed photochemical protocol offers broad substrate scope giving 2-oxazolidinones and 2-oxazinones bea...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2023-11, Vol.59 (92), p.13711-13714
Main Authors: Mandapati Bhargava Reddy, McGarrigle, Eoghan M
Format: Article
Language:English
Subjects:
Amines
Carbon dioxide
Isomerization
Light irradiation
Ruthenium
Substrates
Sulfones
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Summary:An unprecedented carboxylative sulfonylation of (homo)propargyl amines with CO2 and sodium arylsulfinates under visible light irradiation has been developed with high efficiency. This ruthenium-catalysed photochemical protocol offers broad substrate scope giving 2-oxazolidinones and 2-oxazinones bearing alkyl sulfones in good yields under ambient reaction conditions. An in situ double bond isomerisation occurs in tandem. A mechanistic rationale for these radical-initiated carboxylative cyclisations involving sulfinyl radicals is presented, supported by control and quenching experiments.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc04160c