ArticleNature communications2022
[3+2] Cycloaddition of alkyl aldehydes and alkynes enabled by photoinduced hydrogen atom transfer.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Diastereoselective synthesis of substituted cyclopentanonesChemical science · 2026Article
- Photocatalytic Stereoselective Editing of Alkynes to 3D Molecules via Hydrogen Atom Transfer-Mediated Dynamic Epimerization.Nature communications · 2026Article
- Photocatalytic streamlined dual-functional group transfer from cyanopyridine to internal alkynes.Nature communications · 2025Article
- Tetrafluoroisopropylation of alkenes and alkynes enabled by photocatalytic consecutive difluoromethylation with CFNature communications · 2024Article
- Visible Light Promoted [3+2]-Cycloaddition for the Synthesis of Cyclopenta[The Journal of organic chemistry · 2023Article
- Visible-light-induced [3+2] cycloadditions of donor/donor diazo intermediates with alkenes to achieve (spiro)-pyrazolines and pyrazoles.Chemical science · 2023Article
- Asymmetric imino-acylation of alkenes enabled by HAT-photo/nickel cocatalysis.Chemical science · 2023Article
- Design principles of the use of alkynes in radical cascades.Nature reviews. Chemistry · 2023Review
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Authors and funding
7 authors.
Funding
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Abstract
[3+2] Cycloaddition is a step- and atom-economic method for the synthesis of five-membered rings. Despite the great success of 1,3-dipolar cycloadditions, the radical [3+2] annulation of alkynes remains a formidable challenge. Herein, a photoinduced decatungstate-catalyzed [3+2] cycloaddition of various internal alkynes using abundant aliphatic aldehydes as a three-carbon synthon is developed, producing elaborate cyclopentanones in 100% atom economy with excellent site-, regio-, and diastereoselectivity under mild conditions. The catalytic cycle consists of hydrogen atom abstraction from aldehydes, radical addition, 1,5-hydrogen atom transfer, anti-Baldwin 5-endo-trig cyclization, and back hydrogen abstraction. The power of this method is showcased by the late-stage elaboration of medicinally relevant molecules and total or formal synthesis of (±)-β-cuparenone, (±)-laurokamurene B, and (±)-cuparene.
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