The radical chemistry of N-sulfenyl phthalimides/succinimides for C S bonds formation

Xiao, Qian; Zhong, Jian-Ji

doi:10.1016/j.tetlet.2024.155153

Tetrahedron Letters

2024

DOI: 10.1016/j.tetlet.2024.155153

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The radical chemistry of N-sulfenyl phthalimides/succinimides for C S bonds formation

Qian Xiao,

Jian-Ji Zhong

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2024

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Cited by 5 publications

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Photoredox Radical‐Polar Crossover Reaction ofgem‐Difluoroalkenes: A Facile Access to Diverse Difluoroalkyl Sulfides

Liang,

Wang,

Miao

et al. 2024

ChemCatChem

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Difluoroalkyl sulfide (‐CF2S‐) moieties are an important class of skeletons in medicinal chemistry. Herein, a photoredox radical‐polar crossover reaction is reported for the three‐component thiofluorination, thiohydroxylation, thioalkoxylation, thioaminolation, and thiochlorination of gem‐difluoroalkenes towards diverse α‐functionalized difluoroalkyl sulfides. Such an approach features mild conditions, operational simplicity, and good substrate scope.

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Photoredox Radical‐Polar Crossover Reaction ofgem‐Difluoroalkenes: A Facile Access to Diverse Difluoroalkyl Sulfides

Liang,

Wang,

Miao

et al. 2024

ChemCatChem

View full text Add to dashboard Cite

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A General Electron Donor‐Acceptor Photoactivation Using Oxime Esters Enabled Divergent Thioetherifications^†

Lu,

Jiang,

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryThe EDA complex‐mediated reactions involving oxime esters have been few studied. Herein, an EDA complex formed by thiophenolate anion and oxime ester is reported for photoinduced divergent synthesis of thioethers, depending on different types of oxime esters. Operational simplicity, mild reaction conditions, and flexible options of leaving group demonstrate the generality and synthetic utility of this approach. Such an approach can also enable an interesting thiol‐catalysis for the synthesis of phenanthridines.

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Unexpected Formation of a Chiral spiro‐system in the Reaction of the Dilithium Derivative of Hexafluorocumyl Alcohol with N‐(t–butylsulfenyl)phthalimide

Zając,

Żurawiński,

Sieroń

et al. 2024

ChemPlusChem

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An unexpected course of the reaction of hexafluorocumyl alcohol dilithium derivative 2 with N‐(t‐butylsulfenyl)phthalimide (3) has been presented. The process proceeded under mild conditions and resulted in previously undescribed chiral spiro‐system – 3',3'‐bis(trifluoromethyl)‐3H,3'H‐1,1'‐spirobis(isobenzofuran)‐3‐one (5) as the only product. A detailed spectral analysis of the product has been provided, and mechanistic aspects have been investigated. Attempts to separate the enantiomers of compound 5 using a semipreparative HPLC method with a chiral stationary phase column have been described. The repeatability of the reaction using analogs of alcohol 4 has also been tested. DFT calculations of absolute configuration assignment have been performed successfully.

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The radical chemistry of N-sulfenyl phthalimides/succinimides for C S bonds formation

Cited by 5 publications

References 100 publications

Photoredox Radical‐Polar Crossover Reaction ofgem‐Difluoroalkenes: A Facile Access to Diverse Difluoroalkyl Sulfides

Photoredox Radical‐Polar Crossover Reaction ofgem‐Difluoroalkenes: A Facile Access to Diverse Difluoroalkyl Sulfides

A General Electron Donor‐Acceptor Photoactivation Using Oxime Esters Enabled Divergent Thioetherifications^†

Unexpected Formation of a Chiral spiro‐system in the Reaction of the Dilithium Derivative of Hexafluorocumyl Alcohol with N‐(t–butylsulfenyl)phthalimide

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The radical chemistry of N-sulfenyl phthalimides/succinimides for C S bonds formation

Cited by 5 publications

References 100 publications

Photoredox Radical‐Polar Crossover Reaction ofgem‐Difluoroalkenes: A Facile Access to Diverse Difluoroalkyl Sulfides

Photoredox Radical‐Polar Crossover Reaction ofgem‐Difluoroalkenes: A Facile Access to Diverse Difluoroalkyl Sulfides

A General Electron Donor‐Acceptor Photoactivation Using Oxime Esters Enabled Divergent Thioetherifications†

Unexpected Formation of a Chiral spiro‐system in the Reaction of the Dilithium Derivative of Hexafluorocumyl Alcohol with N‐(t–butylsulfenyl)phthalimide

Contact Info

Product

Resources

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A General Electron Donor‐Acceptor Photoactivation Using Oxime Esters Enabled Divergent Thioetherifications^†