ArticleNature communications2020
Radical-mediated C-C cleavage of unstrained cycloketones and DFT study for unusual regioselectivity.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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5 citing papers in PubMed.
- Origin of LiMaterials (Basel, Switzerland) · 2023Article
- Metal-Free Catalysis in C-C Single-Bond Cleavage: Achievements and Prospects.Topics in current chemistry (Cham) · 2022Review
- Computational, Mechanistic, and Experimental Insights into Regioselective Catalytic C-C Bond Activation in Linear 1-Aza-[3]triphenylene.ACS omega · 2022Article
- Solvent-controlled photocatalytic divergent cyclization of alkynyl aldehydes: access to cyclopentenones and dihydropyranols.Chemical science · 2021Article
- Regioselective activation of benzocyclobutenones and dienamides lead to anti-Bredt bridged-ring systems by a [4+4] cycloaddition.Nature communications · 2021Article
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6 authors.
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Abstract
The C-C σ-bond activation of unstrained cycloketones represents an ingenious and advanced technique in synthetic chemistry, but it remains a challenging area which has been largely underexplored. Herein we report an efficient strategy for the direct C-C cleavage of cyclohexanones and cyclopentanones. The cyclic C-C σ-bond is readily cleaved under mild conditions with the aid of an in situ formed side-chain aryl radical. Density functional theory calculations are carried out to shed light on the unusual regioselectivity of C-C bond cleavage. The reaction affords a variety of structurally diverse 3-coumaranones and indanones that widely exist in natural products and bioactive molecules, illustrating the synthetic value of this method.
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