6533b7d9fe1ef96bd126ca7b
RESEARCH PRODUCT
Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates
Olga M. MulinaAlexander O. Terent'evAlexey I. IlovaiskyTill Opatzsubject
Sulfonylchemistry.chemical_classificationDouble bond010405 organic chemistryChemistryOrganic ChemistryProtonation010402 general chemistry01 natural sciencesBiochemistryMedicinal chemistry0104 chemical sciencesCatalysisNitrobenzenechemistry.chemical_compoundDrug DiscoveryPhotocatalysisSelectivityEosin Ydescription
Abstract A metal-free visible light photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates in moderate to high yields is described. The reaction proceeds in ethanol and uses eosin Y as a readily available photocatalyst in combination with nitrobenzene as an electron shuttle. Taking into account the number of steps involved (generation of the sulfonyl radical, its addition to the double bond, elimination of molecular nitrogen with formation of an iminyl radical, followed by its reduction and protonation) as well as the number of redox-active reaction partners involved, the selectivity of the process is quite impressive.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2021-02-01 | Tetrahedron Letters |