ArticleBeilstein journal of organic chemistry2020
Visible-light-induced addition of carboxymethanide to styrene from monochloroacetic acid.
Article in Beilstein journal of organic chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Divergent functionalization of alkenes enabled by photoredox activation of CDFA and α-halo carboxylic acids.Chemical science · 2024Article
- Oxidative Addition of C-Cl Bonds to a Rh(PONOP) Pincer Complex.Organometallics · 2022Article
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4 authors.
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Abstract
Where monochloroacetic acid is widely used as a starting material for the synthesis of relevant groups of compounds, many of these synthetic procedures are based on nucleophilic substitution of the carbon chlorine bond. Oxidative or reductive activation of monochloroacetic acid results in radical intermediates, leading to reactivity different from the traditional reactivity of this compound. Here, we investigated the possibility of applying monochloroacetic acid as a substrate for photoredox catalysis with styrene to directly produce γ-phenyl-γ-butyrolactone. Instead of using nucleophilic substitution, we cleaved the carbon chlorine bond by single-electron reduction, creating a radical species. We observed that the reaction works best in nonpolar solvents. The reaction does not go to full conversion, but selectively forms γ-phenyl-γ-butyrolactone and 4-chloro-4-phenylbutanoic acid. Over time the catalyst precipitates from solution (perhaps in a decomposed form in case of
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