ArticleNature communications2021
Efficient access to aliphatic esters by photocatalyzed alkoxycarbonylation of alkenes with alkyloxalyl chlorides.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 74 citations in OpenAlex.
- Additives Promote Divergent Reactivity in Photolytic Deoxygenation and Lactonization Reactions of Cobalt Alkoxycarbonyls.European journal of organic chemistry · 2026Article
- Enantioselective Alkoxycarbonyl-Lactonization of Alkenes via the Merger of Photoredox and Copper Catalysis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
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- Fluorinated Radicals in Divergent Synthesis via Photoredox Catalysis.Accounts of chemical research · 2025Article
- Stereoretentive cross-coupling of chiral amino acid chlorides and hydrocarbons through mechanistically controlled Ni/Ir photoredox catalysis.Nature communications · 2022Article
- A general electron donor-acceptor complex for photoactivation of arenesChemical science · 2022Article
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Authors and funding
9 authors at 3 institutions in 1 country.
Funding
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Abstract
Aliphatic esters are essential constituents of biologically active compounds and versatile chemical intermediates for the synthesis of drugs. However, their preparation from readily available olefins remains challenging. Here, we report a strategy to access aliphatic esters from olefins through a photocatalyzed alkoxycarbonylation reaction. Alkyloxalyl chlorides, generated in situ from the corresponding alcohols and oxalyl chloride, are engaged as alkoxycarbonyl radical fragments under photoredox catalysis. This transformation tolerates a broad scope of electron-rich and electron-deficient olefins and provides the corresponding β-chloro esters in good yields. Additionally, a formal β-selective alkene alkoxycarbonylation is developed. Moreover, a variety of oxindole-3-acetates and furoindolines are prepared in good to excellent yields. A more concise formal synthesis of (±)-physovenine is accomplished as well. With these strategies, a wide range of natural-product-derived olefins and alkyloxalyl chlorides are also successfully employed.
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