ArticleThe Journal of organic chemistry2015
Fragment Coupling and the Construction of Quaternary Carbons Using Tertiary Radicals Generated From tert-Alkyl N-Phthalimidoyl Oxalates By Visible-Light Photocatalysis.
Article in The Journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed.
- Visible-Light-Induced Radical Cascade [4 + 2]/[4 + 2] Cycloaddition of UnderexploredOrganic letters · 2026Article
- Harnessing Photochemistry in Natural Product Synthesis: From Strategy to Applications.Journal of natural products · 2025Review
- Enantioselective Alkoxycarbonyl-Lactonization of Alkenes via the Merger of Photoredox and Copper Catalysis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Deoxygenative Functionalization of Alcohols and Carbonyl Compounds via Electrochemical Reduction.Angewandte Chemie (International ed. in English) · 2025Article
- Visible-Light-Mediated Rose Bengal- or [Ru(bpy)ACS omega · 2025Article
- Metallaphotocatalytic triple couplings for modular synthesis of elaborate N-trifluoroalkyl anilines.Nature communications · 2024Article
- Strategies and Tactics for Site Specific Deuterium Incorporation at Each Available Carbon Atom of α-Pinene.The Journal of organic chemistry · 2024Article
- Asymmetric synthesis of unnatural α-amino acids through photoredox-mediated C-O bond activation of aliphatic alcohols.Chemical science · 2024Article
- Metal-free photocatalytic cross-electrophile coupling enables C1 homologation and alkylation of carboxylic acids with aldehydes.Nature communications · 2024Article
- A Chemoselective Polarity-Mismatched Photocatalytic C(spAngewandte Chemie (International ed. in English) · 2023Article
- Selective Cleavage of Lignin Model Compounds via a Reverse Biosynthesis Mechanism.Organic letters · 2023Article
- Total Synthesis of Rameswaralide Utilizing a Pharmacophore-Directed Retrosynthetic Strategy.Journal of the American Chemical Society · 2022Article
- Article
- Metal-free deoxygenative coupling of alcohol-derived benzoates and pyridines for small molecules and DNA-encoded libraries synthesis.Chemical science · 2022Article
- Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis.Chemical reviews · 2022Review
- Selective deoxygenative alkylation of alcohols via photocatalytic domino radical fragmentations.Nature communications · 2021Article
- Photoinduced 1,2-dicarbofunctionalization of alkenes with organotrifluoroborate nucleophilesChemical science · 2021Article
- Interrupting the Barton-McCombie Reaction: Aqueous Deoxygenative Trifluoromethylation ofOrganic letters · 2021Article
- Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy.Chemical reviews · 2020Article
- Visible-Light-Induced Alkoxyl Radicals Enable α-C(spiScience · 2020Article
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4 authors.
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Abstract
The coupling of tertiary carbon radicals with alkene acceptors is an underdeveloped strategy for uniting complex carbon fragments and forming new quaternary carbons. The scope and limitations of a new approach for generating nucleophilic tertiary radicals from tertiary alcohols and utilizing these intermediates in fragment coupling reactions is described. In this method, the tertiary alcohol is first acylated to give the tert-alkyl N-phthalimidoyl oxalate, which in the presence of visible-light, catalytic Ru(bpy)3(PF6)2, and a reductant fragments to form the corresponding tertiary carbon radical. In addition to reductive coupling with alkenes, substitution reactions of tertiary radicals with allylic and vinylic halides is described. A mechanism for the generation of tertiary carbon radicals from tert-alkyl N-phthalimidoyl oxalates is proposed that is based on earlier pioneering investigations of Okada and Barton. Deuterium labeling and competition experiments reveal that the reductive radical coupling of tert-alkyl N-phthalimidoyl oxalates with electron-deficient alkenes is terminated by hydrogen-atom transfer.
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