Photocatalytic Activation of Heterocyclic Iodonium Ylides for the Synthesis of Dihydrofuropyranones and Dihydrofuropyridones.

Kelsey T Sumter, Carly Slough, Hayley E Johnson, Catherine S Kesler, Mary Elisabeth Daub

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Article in The Journal of organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 authors.

Kelsey T SumterDepartment of Chemistry, Furman University, 3300 Poinsett Highway, Greenville, South Carolina 29613, United States.

Carly SloughDepartment of Chemistry, Furman University, 3300 Poinsett Highway, Greenville, South Carolina 29613, United States.

Hayley E JohnsonDepartment of Chemistry, Furman University, 3300 Poinsett Highway, Greenville, South Carolina 29613, United States.ORCID 0009-0003-6149-709X

Catherine S KeslerDepartment of Chemistry, Furman University, 3300 Poinsett Highway, Greenville, South Carolina 29613, United States.ORCID 0009-0004-2612-9571

Mary Elisabeth DaubDepartment of Chemistry, Furman University, 3300 Poinsett Highway, Greenville, South Carolina 29613, United States.ORCID 0000-0002-1368-9607

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

β-Distabilized iodonium ylides undergo photocatalytic activation using neutral eosin Y and visible light to afford dihydrofuropyranones, dihydrofuropyridones, and dihydrofurans. Steady-state absorption spectroscopy and application of the method of continuous variations to complexation-induced chemical shifts provide evidence for the binary complexation of eosin Y and β-distabilized iodonium ylides. Preliminary mechanistic studies using transient absorption spectroscopy suggest monoanionic eosin Y as the active photocatalyst functioning via an oxidative quenching cycle. This simple approach to enhancing the reactivity of heterocyclic iodonium ylides expands the scope of their use as building blocks in the synthesis of heterocycles.

Identifiers

PMID40934390

DOI10.1021/acs.joc.5c01187

PMCPMC12481581

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